FRONT MATTER
SECTION 1
Thank You 1Password
This book is a gift, courtesy of the folks at 1Password, the best password management solution. While you are getting better at your email, don’t forget to secure your passwords.
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A Note from Dave at 1Password To all our amazing customers. We wouldn't be here without you. Thank you for enabling us to work at our dream jobs. –Dave Teare
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Dedication
To Alisa, with much love.
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SECTION 4
Acknowledgements You get a cookie.
Merlin Mann, David Allen, and E. B. White. My thanks also go to the hardworking software developers and engineers who made the great email applications and services that make taming email possible. I did not include anything in this book that I didn’t feel was useful and a potential solution for my readers.
So many people helped make this book possible. First, I want to thank my family. Daisy, Samantha, and Sarah were all troopers, letting me spend countless hours researching, writing, and screencasting to make this book possible. I also want to thank the many teachers I’ve had along the path as I figured out how to deal with email, including
For some time, I’ve admired Mike Rohde’s sketches. I’m thrilled that he 5
agreed to illustrate this book. Darren Rolfe has helped me with every cover of the MacSparky Field Guides and for that I’m eternally grateful. I’d also like to thank my principal proofreader, Leilani Resurreccion. I also had an intrepid group of friends that offered their time and feedback including J.F. Brissette, Jean MacDonald, and Eddie Smith.
Finally, thank you MacSparky readers and Mac Power Users listeners. I cannot overstate how much love and appreciation I have for each and every one of you.
There is also a group of people at Apple that built the iBooks Author tools and manage the iBooks Store. I’m one of the smallest publishers in the iBooks Store but they don’t treat me that way. These books would simply not exist without the hard work of the entire iBooks team.
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David Sparks, November 12, 2013
SECTION 5
About David Sparks David Sparks is a productivity con man who claims to help you get more efficient with your technology but can just as easily wreck your day with some bit of fiddly awesomeness. David publishes MacSparky.com (website), where he writes about getting the most out of Apple technologies. Additionally, David contributes to Macworld magazine (website). David writes and publishes the MacSparky Field Guides (website) that include
Paperless, Markdown, and 60 Mac Tips. David also wrote two previous books, Mac at Work and iPad at Work, which a lot of people seemed to like. David cohosts the Mac Power Users podcast (website) where he, along with Katie Floyd (website), routinely tackles technology and workflows in excruciating detail. David also speaks about technology at places such as Macworld/ iWorld and the American Bar Association. 7
When David isn’t speaking and writing about technology, he practices law in Orange County, California, and spends his time with his wife and two daughters.
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SECTION 6
The MacSparky Field Guides The MacSparky Field Guides exist to turn their readers into bad-ass wielders of technology.
The MacSparky Field Guide series -Official Mission Statement is a nutty idea cooked up by David Sparks to publish quality, exhaustive guides for getting the most from your Apple technologies. They are intended as a soup-to-nuts explanation for people who want to get some serious work done. These books go into glorious, agonizing detail about practical technology solutions. 9
The MacSparky Field Guide series are intended to be the Pixar movies of tech books with excellent execution, cutting-edge technology, and, at the end of the day, a good story for the reader. Throughout the Field Guide series, David Sparks demonstrates workflows and applications to help you along.
This book is a mixture of finely crafted words, photo galleries, interactive images, screencasts, and audio interviews all designed to make you the boss of your email. There is nearly an hour-and-a-half of video in this “book”. You, my friend, are about to receive your email black belt.
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1 of 12
Most presentations are terrible. That, however, does not need to be the case for your presentations. This Presentation Field Guide explains how to plan a presentation that will connect with your audience, the technical wizardry to create a stunning presentation, and walks you through presentation day to make sure it goes off without a hitch. The material is accessible to beginners and power users alike with a thoughtful, fun, and systematic approach to planning, creating, and delivering a stellar presentation. There’s even a video. (website)
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Paperless takes the mystery (and fear) out of going paperless with your Apple technology. The material is accessible to beginners and power users alike with a thorough explanation of all the hardware, software, and workflows necessary to finally conquer paper.
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Markdown started as a clever way to write for the web but has become so much more. This book demystifies Markdown, making it easy for anybody to learn. You can go from no knowledge to Markdown pro. It will change the way you write forever.
1 of 11 13
60 Mac Tips is a carefully built list of tips and tricks to make you more efficient on your Mac. The book explains why each trick is special and most include a screencast showing you how to perform it on your very own Mac. Carefully paced, this book takes intermediate and beginner Mac users and turns them into Mac power users.
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SECTION 7
How to Read This Book This “book” is a brave new venture into a multimedia something. This book is sold in the iBooks format through the Apple iBooks Store for the Mac and iPad and as a PDF file. This is the PDF version. The PDF version includes all the movies and gallery
photos from the iBooks version but not in the self-contained iBooks format. Instead, this PDF download includes the PDF file, which you are now reading, and several folders with all of the screencasts and photo galleries from this book. There are several screenshots of videos in this book but in order to see the videos themselves, go to the accompanying folders. A BRIEF WORD ABOUT LINKS There are several links in this book that take you to websites, app stores, Twitter, Wikipedia, and YouTube. For some readers, 15
these external links are jarring in that they take you out of this PDF and in and into some other application on your Mac or iPad. I put these links in parentheses or brackets so you, dear reader, know when you are about to kick yourself out of this book. Want to see how that works? Press this (YouTube). Now let’s go tackle email together.
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SECTION 8
Email Field Guide Update Log Every MacSparky Field Guide gets free updates for two years after its initial publication date. (This book was originally published in November 2013.) My goal is to keep the book current with the latest workflow updates, apps, and technologies. Here is a list of the changes.
❖ Added new section on Apple Mail Drop. ❖ Added new section and screencast on the Apple Mail Markup Extension. ❖ Added new section and screencast on minimizing draft messages on iPad and iPhone. ❖ Updated section on Swipe Options based on iOS 8 improvements.
VERSION 1.2, NOVEMBER 2014 ❖ Added additional Gmail backup solution, Backupify
❖ Added an explanation of Apple Mail Handoff.
❖ Added Google Takeout to archiving chapter. 17
❖ Added a new section for VIP Threads in Apple Mail.
❖ Converted Email Port list into a table ❖ Added Apple Mail archive keyboard combination
❖ Added Key Rocket for Gmail Chrome extension
❖ Rewrote the description of MailMate based on recent developments
❖ Added bacn remover Unroll.me ❖ Updated for Microsoft Outlook 2014
❖ Added additional screenshots to the Outlook Gallery
❖ I topped the coolant and wiper fluid
❖ Added explanation of yearly archives VERSION 1.1, DECEMBER 2013
❖ Added an explosion video sans advertisement
❖ 100% better controls on the audio interviews
❖ Squashed typos
❖ Fixed my misguided confusion between carbon paper and mimeograph
❖ Added 1.21 jigawatts to the the flux capacitor
❖ Fixed Screencast 4.20 VERSION 1.0, NOVEMBER 2013
❖ Changed the recommended write order to add recipient last
“It’s Alive!” (YouTube) 18
CHAPTER 1
THE EMAIL PROBLEM
SECTION 1
The Email Problem museum a collection of richly composed correspondence between loved ones and not-so-loved ones that really give you a window into their world and thoughts. I even saw this with my own parents’ correspondence. With the advent of the telephone, however, that all changed. Most people of my generation never got into the habit of writing letters to one another. We called each other on the telephone (and now we text). It always felt to me as if we left something special behind.
I’ve always had this thing for the way people used to write letters to one another. Look at anybody worth remembering from the beginning of recorded history to the mid-20th century and you will find in some
Then email arrived.
20
I got my first email account in 1988. As a nerd with a closet letter fetish, it seemed that email was the perfect solution. So I started looking for friends with email accounts whom I could write with Winston Churchill-calibre aplomb. In those first few years I wrote some real doozies. Before long however, my email correspondence became decidedly less archival and much more practical. Moreover, my email correspondents shifted from my dearest friends to people interested in helping me get rid of my pesky cash for highly dubious products, services, and “enhancement” drugs.
got sloppy. Even worse, there was a lot more of it and I began to let email run my life. Then I started writing books, producing podcasts, and otherwise putting myself out there. The email problem that I was barely managing blew up in my face. I can even tell you the exact moment that I realized my email problem was out of control. It was shortly after Paperless was released and I was working through a big stack of emails. It was becoming a daily chore for me. For hours every day, I was digging myself out while sitting on the couch. During the same period my 11-year-old daughter was building something with a particularly daunting set of LEGO bricks. So that’s how it was: Dad emailed, Sarah built. I finally responded to the last email and looked down to see Sarah had finished with her LEGO
This transition was gradual and unexpected. At some point, I became conscious of it and slowly my attitude (and enthusiasm) toward email changed for the worse. My emails became much shorter and my email habits 21
set. I didn’t get to help her with a single brick. As if on cue, I then received an email from a reader who chastised me for not responding to her email that she sent six days earlier. It read: “Since you don’t take email seriously, I recommend you remove your email address from your website.” My reaction was not subtle (YouTube).
Mr. White. He was carpet-bombed with letters and responding to this mail (not writing more books) took all of his time. (E. B. White did not publish another children’s book until 1973.) He became so frustrated with the mail that he somewhat in jest asked one young correspondent to “start a movement in America called ‘Don’t write to E. B. White until he produces another book.’”
This problem is not new. E. B. White wrote Charlotte’s Web in 1952 (Wikipedia). I think everyone could agree it was a pretty good E.B. White book. The trouble was that every teacher and librarian in the country started instructing schoolchildren to send letters to
When a school librarian saw his response, she wrote to him complaining. E. B. White replied, explaining how the practice of having all of these children write to him was overwhelming. He went on to explain how he had an idea for a new novel and had started working on it but was unable to begin writing in earnest because when he looked at his desk, all he could see were “the unanswered letters and the undone things 22
[that] lie in accusing piles”. E. B. White, one of the greatest novelists in American history, concluded, “I get impatient with the morning mail, because it is, in a sense, my enemy—the thing that stands between me and a final burst of creative effort.” Sound familiar? You can read the entire letter, which is fascinating, in the sidebar. (Source: Letters of Note [website].) The problem is that email is endless. Some of it comes from people with good intentions, and a lot of it comes from robots or people who don’t give a damn. Every email (good-intentioned or not) creates its own sense of urgency that, if humored, will seem more important than going to work, paying the bills, and (ridiculous as this sounds) even building a LEGO set with your daughter. The more you engage in email, the more email engages you. Put simply, there isn’t a simple solution to the email problem. Everybody has to make their own peace with it as best as they can. However, using the best tools, the automation your 23
E. B. White: The morning mail is my enemy.
North Brooklin, Maine May 7, 1961 Dear Miss B., I’m sorry this letter has been put off for so long, but there has been serious illness in my family and I have let things slide in consequence. I was surprised when my letter to Cathy Durham was returned to me by you. Of the thousands of letters I have written to children, it’s the only one that has bounced, and I don’t feel quite sure what happened. I assume you were disinclined to exhibit it, but I think the letter belongs to Cathy and if you’ll send me her address I’ll return it —she might like to have it about
computer can provide you, and a little common sense, you can make a bad situation much more bearable. That is really the point of this book: to confront email, to help you make smart decisions about how to deal with it, and to provide you the right tools to pull it off. It took that lost moment of not being able to play with Sarah for me to realize I needed to become the boss of email and not vice versa. That is exactly what I’ve been doing for the last year—studying, experimenting, and developing new workflows that let me tame the beast and even, once in a while, build something really cool with my daughter.
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CHAPTER 2
TACTICAL EMAIL
SECTION 1
Getting Tactical So how do you conquer email? There are two levels to the problem: tactical and technical. On the technical level, there are a lot of different tools, applications, and services to help you. This book is going to make you a PhD on the technical side of email for your Mac, iPad, and iPhone.
the tactical level. Whether you write email exclusively on your iPhone with the stock mail app or instead write email on your own custom mail application on your Mac, there are certain email techniques universal to all email systems. These tactical-level issues range from what to do with your inbox to how to handle email signatures. This chapter will focus on the best techniques for dealing with email on this tactical level and gives you ideas you can use in any email program (even non-
But before we dive into the nitty-gritty, I’d like to spend some time looking at email on 26
Apple operating systems). This chapter is going to discuss several principles of email that I will be referring to throughout the book. Where the rest of the book discusses the how of email, this chapter explains the why.
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SECTION 2
Your Inbox YOUR INBOX IS NOT YOUR TASK LIST
and keep it for later. (There is a book on that: Paperless [iBooks Store]).
Imagine that mailbox outside your house. There is a pretty simple workflow involved with paper mail. A very nice postal worker (usually they’re nice [YouTube]) arrives at your abode and crams lots and lots of paper into a little box. You then fetch the paper and sort through it. You throw some of it away. You read some. You may even scan some
The one thing you are not going to do is walk out to your mailbox, look through your mail, and then stuff it all back in your mailbox, wishing the postal worker luck getting tomorrow’s load into the already full box. That would be crazy. Nevertheless, crazy is what a lot of us do every day. We look through our inboxes at things we’re not exactly sure 28
what to do with, close the window, and go back to Twitter or Facebook or whatever else helps us release our happy chemicals while we try to forget the piles and piles of electronic mail sitting there.
bankruptcy”. Many people will mindlessly delete great big piles of important email with no actual plan in mind and then immediately resume the bad habits that got them there in the first place. This is something like an alcoholic throwing out all the whisky only to head to the liquor store an hour later. There is a better way.
The next time we go back to our email clients, we see the exact same emails we ignored last time plus a whole new pile of mail dropped there while we were away. At some point it becomes paralyzing. EMAIL BANKRUPTCY
One solution is to add a secret email address. Some people do this in effort to avoid a lot of the email noise. They set up a secret email address and only provide it to those nearest and dearest to their heart. The problem is that inevitably this email address gets distributed wider than you wanted and
So we struggle through this dysfunctional relationship with our electronic mailbox until one day we open our email clients and feel as if we are getting sucked into a sarlacc pit (Wookieepedia). For a lot of people, this leads them to simply delete the entire contents of their inbox and declare “email 29
PROCESSING YOUR INBOX
you’ve still got the overload problem on the “public” email account.
Leaving all of your emails in your inbox makes as much sense as leaving all of your paper mail in the mailbox in front of your house. You need to process your inbox. In 2007, my friend Merlin Mann gave a Google Tech Talk about email called “Inbox Zero” (website)(video). The talk is legendary among the geek community and for good reason: it is dripping with good common-sense advice about tackling your inbox.
You can’t ignore that original account either because occasionally something comes in and it is important to you, so now you’ve got two accounts to deal with. Moreover, some friends will start sending you messages to both accounts simultaneously and then all hell breaks lose. You’re better off applying filters and using some of the other techniques covered in this book and keeping just one email address.
There is a workflow that can help you avoid email bankruptcy. With a little practice, you can get really good at going to your mailbox and leaving it empty. Here are the steps to inbox bliss:
If you’re reading this with an inbox count of four digits, you’re not alone. Don’t despair. Instead of declaring email bankruptcy, send your existing emails to an archive (so you can at least search it later) and start fresh using the techniques from this book.
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1. IF IT’S TRASH, TRASH IT. IMMEDIATELY.
For instance, I may receive a greeting card from a friend: “Dear Dave, I sure am glad you got that thing removed. You don’t look nearly as hideous as you used to. Cheers, Jimbo.”
It is easy enough to trash offers from Nigerian princes. (However, with a good system for dealing with spam, covered in Chapter 7, you shouldn’t need to see email from Nigerian princes.) There are a lot of other emails that may not seem as obvious trash can fodder but still are. These are emails that you can see no possible reason for ever needing again. Perhaps it is because we have these digital things in our lives and it feels as if they have unlimited storage, but I find myself much more resistant to trashing email than I am to trashing similar paper mail.
The card may make me feel all warm and squishy inside. It may even have a picture of a kitten hanging from a branch on the cover. Regardless, after a day or two I’ll throw it away. However, I have trouble trashing even the most mundane email I receive from Jimbo (even that one thanking me for feeding his pet gator Felix). Why is that? Maybe it is because emails don’t take up physical space in our lives so we are more likely to keep 31
them. Nevertheless, they do take physical space on our computer storage devices. Moreover, they take up room in the email indexes our computers must track so they can search out email for us. If the email truly is trashable (even from a loved one), trash it.
friends here. Almost everything I don’t delete ends up in the Archive folder eventually. Note that it is an Archive folder (singular), not Archive folders (plural). Back in the day I had lots of folders to hold old email. I had folders for friends and family. I had folders for the day job. I had folders for every case I worked on. I had folders for emails from my favorite online news groups. You name it, I had a folder for it. Before long my email client had this long scrolling list of folders.
2. IF IT’S ARCHIVAL, ARCHIVE IT. If Jimbo writes to tell me what a swell guy I am (some people think I am), I may decide that is one worth keeping. Maybe I’ll want to read it the next time I need to buoy my delicate sense of importance. That’s an email requiring filing but no response. (What do you say to someone telling you what a swell guy you are?) Emails such as that go in the Archive. On all of my email accounts, I’ve got a mailbox labelled “Archive” where I dump emails. I don’t just send emails from 32
Then I had to carefully click and drag each email to its appropriate folder. If I missed and dropped the email in the wrong folder, I had to go drilling to find it and put it in the right place. I also found myself facing an existential crisis every time I had an email that could potentially fit in multiple folders. Does this email go in the Jimbo, Friends, or Gator folder? Because I was crazy, I probably created a new folder called “My Friend Jimbo’s Gator”. If that is you, stop the madness. Every email client in this book has a remarkable search engine. I’m going to teach you how to use them in later chapters. With all of my email in a single folder, by typing Jimbo and gator in the search box, I can find that same email with zero upfront investment of time labeling and filing. All of that time you are spending
carefully creating, organizing, and filling that detailed folder hierarchy is wasted. With modern email clients, you can dump it all in one folder and you will find it. There are some exceptions to this rule, and I’m going to explain those further later in this book, but the big point here is that the days of filing emails in particular folders are largely over. If you are reading these words and the idea of using just one archive for your email is sending cold chills down your spine, my advice would be to try it for a short time. You will probably find you spend less time sorting mail and still can find whatever you need. Some people will create single year archives, like Archive 2013 and Archive 33
2014. That way, they can move the archive out of their email application at the end of the year. If you absolutely must have folders, try your best to limit it to no more than ten. Give yourself at least a fighting chance to not get lost in the morass of mailbox folder hierarchy.
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3. IF YOU CAN RESPOND QUICKLY, THEN RESPOND QUICKLY.
Date: November 12, 2013 10:05 AM To: Jimbo
If the mail is not trash or immediate archive fodder, you’re going to respond to it. If it is a short email that you can respond to without a lot of time or effort, do it right then and there.
From: David Re: Gator Kebabs Dear Jimbo, Umm … no. xoxo, David
There are a lot of emails you can respond to quickly. Productivity nerds (because they are productivity nerds) like to get “scientifical” about this. Some say only answer if you can do so in two minutes. Others say five. I really don’t care. If you can respond quickly and get it out of your life, go for it. Then archive the original email and get back to whatever blows your hair back.
Date: November 12, 2013 10:00 AM To: David From: Jimbo Re: Gator Kebabs Hey Big Dav-o, I was wondering if you’d like to spend Labor Day with me on the swamp. I just got a new banjo and my gator kebabs are to die for. Your pal, Jimbo
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4. IF YOU CAN’T RESPOND QUICKLY, RESPOND LATER.
After lovingly responding to the emails in the Action folder, you can send them to the —wait for it—Archive folder.
If you don’t have time to respond or you need to think about it more before sending a reply, put the email somewhere else where you can find it and reply later. One of the easiest ways to accomplish this is to create an Action folder. Over the course of your day (or two), you’ll collect emails in this folder and when you’ve got more time you can go through the Action folder and respond. So when you read that email from an old friend asking you to attend a screening of a documentary on pork rinds and you are torn between the desire to see your friend and the certainty that just watching a film on pork rinds will make you ill, you can move the email to the Action folder and deal with it later.
There is a trap that comes with using an Action folder. If you are unable to routinely empty that Action folder, you’ve just created the same overstuffed inbox with a different label. Once you start using an Action folder, make a promise to yourself that you’ll empty it out every few days. If you find that doesn’t work for you, you’ll have to look at some the other options outlined in this book such as server-side email filtering, deferred email, and other magic tricks you’ll master before finishing this book.
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5. IF THE EMAIL REQUIRES EVEN LATER ACTION, SAVE IT FOR LATER.
time. Doing so will lead to you falling off the wagon, and before long you’ll have hundreds of these emails piled up. These emails create future tasks. It could be as simple as writing a reply or much more complex such as setting up a binary filing system. The point is you shouldn’t be managing that task by leaving the email in your inbox. Instead, create a task in a task application and then send the email into the archive.
Some email requires a response that takes longer than the day or two you need to work through your Action folder. This may be an email that by its nature can’t be answered that quickly (e.g., “Write me back in two weeks about the status of my kumquat plants.”) or something that is going to take more time than you have to dedicate in the next few days (e.g., “Send me the status report once you’ve finished labelling all the office supplies in binary and reorganized them numerically.”). These emails shouldn’t sit in the inbox or Action folder for weeks at a
There are several great Mac and iOS applications to pull this off. Apple’s Reminders app is free and syncs with iCloud between your Mac, iPhone, and iPad. On your Mac you can drag an email out of Apple Mail and drop it in 37
Reminders to create a link so you can jump right back to the message later. Then assign a future date to the reminder and you’re set.
(website) for this purpose. Those aren’t the only options, but they are a good start. The point is that you need a trusted system for setting up tasks for future email responses so you can get them out of your hair right now and get back to work.
I use OmniFocus (iPhone App Store) (iPad App Store) (Mac App Store) (website) to keep track of tasks. (If you want to learn about OmniFocus, check out my screencasts [website].) Some people use Evernote
I walk through all of the steps of processing my inbox in screencast 2.1.
Screencast 2.1 Clearing Out My Inbox
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ADDING COMPLEXITY Having just a few places to sort mail makes a lot of sense, but sometimes it is not enough. While this workflow is a great start, it’s not the only (or necessarily best) solution for everyone. At the end of the book, I’m going to outline my personal workflow in detail, and it includes a lot more steps than this. Specifically, I am using various bits of software and Internet mojo to filter all incoming email into mailboxes relating to the different facets of my life, and I deal with those with different frequencies according to their relative importance. I’ll explain all the tools I use in this book and my workflow in detail in chapter 10.
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SECTION 3
Email Notifications At some point along too much email, make The first thing we do, let’s kill the Ding. the way of email no sense whatsoever. It’s software like having someone in development, somebody had the idea of your house tap you on the shoulder every adding a notification system to your time a commercial plays on the email client. Because each and television. The Ding is evil. every one of us is our own very Seriously. special flower, we need to be Stop and think about it for a notified at the very moment minute. Every time you get any someone writes us. Maybe this type of momentum going with made sense back when we your work or, even worse, at received two or three emails a play, that Ding goes off. What day. Maybe. However, is the result? A rebellious piece of notification systems in this day your brain disengages from and age, where everybody gets way 40
whatever real work you are doing and thinks that it may be the most important email in the world. Like some Pavlovian dog, you then pull your phone out of your pocket or switch windows on your Mac to your mail application to find out that you’ve been made an unbelievable offer for Dr. Funkenstein’s Fancy Hair Tonic. At that point, you’ve successfully enabled someone creating spam on the other end of the planet to interrupt your work or play. Here’s the corker: in five minutes it is going to happen again. Now think about the number of times that can happen in a day. By default on the Mac, Apple Mail checks your email every five minutes. On your phone, push notifications will do it more frequently, indeed with every new email. Let’s just stick with five minutes to be conservative. A notification every five minutes means 12 interruptions an hour. Assuming that you are around computers or cell phones 12 hours a day, that is 144 interruptions a day. It gets worse when you start thinking in terms of weeks, months, and years. So the question becomes what possible benefit are you getting 41
How many email interruptions? A lot.
1,008 per Week
4,320 per Month
52,560 per Year
out of notifications that you are willing to allow your iThingies to interrupt you 52,560 times per year? Moreover, if you do think it is somehow worth it, how on earth do you get anything done or enjoy any downtime? I think it’s madness and everybody should turn it off.
go to email, and discover that the email isn’t from Apple but instead a dodgy person on the far side of the world who has $2.5 million for me just as soon as I give him my credit card and Social Security numbers. Email has the word mail in it for a reason. By definition, mail (and email) is a delayed form of communication. You write something down, you lick a stamp, and you send it off. While email is 7,842 the digital equivalent of that, it works the same way. Once you press the Send button, there should be no expectation that the other person will immediately receive it and reply. There are other forms of communication for that (such as the telephone and, to a lesser extent, text messaging). People that expect
Badges are the same. Who can avoid that mocking red circle telling you that now you have four unread messages? My trouble is my imagination. I look at that badge and I begin to think the answer to all of my problems might be in there. Maybe someone at Apple likes my book so much they’ve decided to buy 100 million copies so they can ship it on every new iPad. Then I stop everything I’m doing, 42
you to immediately read and reply to their emails are wrong, and you should not adopt your behavior to fit their neurosis.
through the roof. What is wrong with you? Don’t you understand technology? (Sadly, the above exchange is barely fictional.)
In my day job, I’m a lawyer. There are lots of lawyers who have an inflated sense of their own importance. Routinely, I get telephone calls from attorneys like this:
I check my email once in the morning, sometimes at lunch, and always in the late afternoon. That is enough. Over the years, I’ve received phone calls from lawyers, clients, and even judges all complaining that I didn’t receive and respond to their email within minutes of them sending it to me. Every time I have the same discussion, explaining I don’t check email 12 times an hour. Those people that care have figured out that if they need an immediate response from me, they can call me on the telephone. You shouldn’t feel the need to immediately respond to every email you receive. The Onion (website) agrees.
Other guy: Did you read my email? Me: What email? Other guy: That email I just sent you. It’s so important. I can’t believe you didn’t read it. What is wrong with you? You are a bad person. Me: When did you send the email? Other guy: I sent it five minutes ago. I’ve been sitting here waiting for your reply. My blood pressure is going 43
My advice is to immediately start turning off notifications, badges, new mail sounds, and everything else that can get between you and your work (and play). I can hear your thoughts at this moment: That’s all fine and dandy for you, Mr. Fancy Pants, but if my spouse/boss/clients/parents/ kids/stalkers email me, I need to know immediately. I get that. I even have a few of those types of people in my life, too. There are ways to let those people through and later I’m going to show you how to do that, no matter what email system you use. The point is, however, those people are the exception, not the rule. That way when you do get a notification, it truly means it is something worth the interruption, not a smoking deal on Viagra.
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SECTION 4
Writing Email So far, I’ve covered the tactical part of receiving email. Now I want to look at writing email. There are a number of practices you can adopt with the way you reply to email to make life easier for you and your correspondent.
The default write order starts out with you selecting the recipient for your message, which makes enough sense, but then everything goes off the rails. Next, it wants you to type in the subject line for a message you haven’t written yet. Because you haven’t written the message, there is a bit of mental friction between us getting our thoughts together and making a cogent subject line at that time, so we skip it or just leave it with whatever the mail client added (e.g., “re: re: re: re: re: That Thing”).
REPLY WRITE ORDER I’ve always had a gripe with email application developers concerning email replies. When you go to reply to an email, the tab order is all out of whack.
Next, the application wants you to write the body of your message. Rarely does the 45
application even prompt you to add an attachment, which means about half the time you’ll forget to add an attachment. Because the default write order is all out of whack, so are the messages we often send using it. It makes a lot more sense to add attachments next and then write the body of the message before filling out the subject line and sending. I’ve got an alternative write order that makes a lot more sense.
The next thing you do is write the message. That’s the reason you started this whole process. I have some very specific ideas about how to write the message body with inline replies—and explain that later in this chapter—but for now get into the habit of writing the message body next. Also on the subject of the message body, try and keep it brief. Email is a problem for everyone and sending a 3,000-word screed when all you really want is to borrow the industrial plunger isn’t very nice.
1. Add Attachments Don’t you hate getting an email making reference to a nonexistent attachment? Don’t you hate even worse when you send an email making reference to an attachment you forgot to attach?
3. Add a Sane Signature Email signatures should be simple and smaller than the body of the message. There is more on this later in this chapter.
2. Compose the Message Body
46
4. Write the Subject Line Finally, after you’ve attached any necessary files and written everything else, make an intelligent subject line.
Write Order According to MacSparky
5. Enter the Message Recipient and Copies Waiting until last to add the recipient assures you’ll never suffer from premature email sendation. 6. Proof and Send Read the whole thing one last time and send it off into the world.
47
EMAIL RECIPIENTS
actually remember doing this in high school.) People back then didn’t make the decision to Cc someone lightly because they knew what a pain in the neck it was. The trouble with email carbon copies is that they are ridiculously easy to pull off. Type in another name in a Cc field. That’s it.
That Cc in your mail client stands for carbon copy, which itself is a reference to the old days when a copy of a document or letter was made with carbon paper. Anyway, the old folks would literally make a carbon copy and send it off to someone else when it seemed appropriate. This isn’t a new problem. Thomas Jefferson even had a system for copying his letters as he sent them out (website).
Cc
As a result, once people figure out the Cc field, they go crazy with it. I get carbon copied on emails that I have no business reading. Sometimes they do it to cover their backsides. Other times they do it to show how smart they are. Nearly every time they do it, they take a little bit more of my time and attention without a good reason. Be stingy with those carbon copies. Only Cc somebody who really needs to be in the loop and has something to add.
Back in my day, we went past carbon paper to the mimeograph (Wikipedia) but it was still a big deal. You had to get this really smelly fluid, type the letter on special paper, and then roll the paper through a machine like some Gutenberg-inspired artisan. (I 48
Another ugly side effect of carbon copy abuse is the Reply All button. If you are trying to share information or schedule a meeting between several people, Reply All makes sense but otherwise, step away. So often I’ll get a message from someone copied to 20 other people announcing their dog got rid of its fleas, they just graduated at the top of their rehab class, or something else they felt like telling everyone they knew. When I receive these notes from friends, I’m happy for them but I also groan inside because I know that within minutes, and continuing for the next week, my inbox will be under attack from Reply All replies. Other recipients get the message and, either through ignorance or in attempt to show everyone else how clever they are, Reply All with their pithy response, which eggs on others in the group to reply to that and before long my email is exploding with
unwanted correspondence. (There is a way to autodelete these strings with email rules, covered later in chapter 4.) Stop the madness. Stay out of these selfcongratulatory email chains. If you want to send a note of congratulations back to your friend, reply to your friend directly. Do not Reply All. That way your friend gets your note about what a unique and special snowflake they really are, and you don’t show up in 20 other people’s mailbox. Then set up your rule and punch eject.
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On the subject of Reply All, treat that button like a loaded gun. Reply All has resulted in more hurt feelings, firings, lawsuits, divorces, and other forms of social disharmony than any other setting on your computer. Every time your mouse hovers over the Reply All button, your Spidey senses should tingle and you should ask yourself, “Do I really want to reply? To all?”
Bcc
horse-sized duck?” This event, dubbed the
“Replyallcalypse”, is legendary on the Internet (website).
A final, cautionary tale on Reply All. In 2012, a student at NYU was trying to forward an email from the Bursar’s office to his mom. He accidentally hit Reply All and ended up sending that email to 39,979 NYU students. The recipients, being college students and grasping the potential for anarchy, immediately began Replying All to 39,979 people with probing questions such as “Can I borrow a pencil?” and “Would you rather fight 100 duck-sized horses, or one
The final subject of consideration is the Bcc (blind carbon copy) field. This also has long roots in the pre-computer world. If you 50
were sending a letter to Franklin and a secret copy to Eleanor, you’d blind carbon copy Eleanor and Franklin would be none the wiser. You can do that now by putting Eleanor’s email address in the Bcc field on an email to Franklin. Eleanor will get a copy of the email and Franklin will never know. As an example, when I send emails to the opposing attorney on a lawsuit, I always Bcc my client. That way the other attorney does not get my client’s email address, and my client knows what I’m up to. I think you can go too far with Bcc. At some point, secretly blind carbon copying everyone just becomes spooky. Use it where appropriate, but don’t get paranoid.
discussion. You want to tell everyone that you just won a cow chip throwing contest. (Yes, they exist [website].) However, you want to be a a good Internet citizen and not give everyone on your mailing list the email address of everyone else on your mailing list. What to do? Blind carbon copy everyone on your list. When you send that email, the recipients will only see your email address and theirs. Not only does this protect your friends’ email addresses from unwanted disclosure, it also prevents that carbon copy cataclysm I wrote about earlier.
Another appropriate use of the Bcc field is sending out a notice to a big group of people while at the same time preserving their privacy. Let’s go back to the carbon copy 51
SUBJECT LINES THAT MATTER
Re:
At some point, it became okay to send an email with a subject line that looked something like this:
Request to Borrow Your Industrial Plunger
The Cost to Replace Your Plunger?
I think the hangup with subject lines has a lot to do with the fact that every email client prompts you to type a subject line before your message. The trouble is we aren’t exactly sure what the subject line should read until after we write the message so we skip it and then never go back. (See the previous section about write order.)
“Re: re: re: re: re: re: Question?”
When you are looking at a list of 50 emails, how does this help you? If you are going to take the time to write me, why not take a few more seconds and help me out with a discernible subject line?
This collective ethic that it is okay to send emails with lousy subject lines sucks. I’ve surely done it enough times myself, but it’s time to stop this. If we are going to help each other conquer email, we have to start spending a few more seconds writing subject lines that make sense.
The best subject lines convey a short version of the key points and questions posed, for example:
Confirming Lunch Tomorrow
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There are some other commonly accepted shortcuts to use in subject lines. EOM means end of message. For instance, you could send an email with a blank body and a subject line that reads, “Yes, I will buy your kumquats. EOM”. Then your recipient knows the entire contents of your message without opening it.
simple and don’t use many. If you can effectively use EOM and NNTR, you are already way ahead of the pack. This isn’t rocket science. Imagine you are on the other side of that email and you’ve got another 200 emails alongside it. Also imagine that you have no idea what the purpose of the correspondence is as it arrives because the the subject lines look like they were typed by 10,000 monkeys with 10,000 typewriters. Now look at your subject line and decide whether or not it’s good enough to convey the key information to your recipient. Start doing this right now and your email correspondents will love you more than their first big fluffy teddy bear.
NNTR is another popular shortcut that means no need to reply. An NNTR message could have a message body. NNTR tells the recipient they don’t need to continue the lunacy by writing back with something inane. There are others such as “Action”, “Time Sensitive”, and “Low Priority”. There is, however, a line with this stuff. If, for example, you need a guide for these codes, you’ve gone over that line. Keep them 53
INLINE REPLIES
the specific part of the letter we were addressing.
Back when we all had quill pens and parchment to communicate with each other, we had to do a lot of signposting in our correspondence.
With email, both of those problems are solved. We reply to an email and the recipient can see the original text right in your reply. Also, the original text is somewhere in the reply so we don’t need to restate the original subject. The question becomes how effectively we leverage these benefits.
An Old-Timey Letter
Dear Sebastian, I am in receipt of your letter dated August 1, 1776. In reference to your recent bout of hookworm infection, I recommend much leeching and bleeding. Cordially, Alexander
By default, every mail client I’ve ever used sets up top-posting replies. That means you type the reply to an email with all of the text of the original message below it. This is not ideal. Top-posting requires the recipient to decide exactly what you are talking about, which isn’t always easy.
Back then we had to tell the recipient (1) which letter we were responding to and (2)
Take, for instance, this email.
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As the reader you can imply that Wolfgang agreed to the loan and forbad the medical disclosure, but are you sure? The reason we do top-posting replies is because they appear easier. I’d argue they aren’t easier because in order to send a top-posting reply correctly, you have to go back to the old days and summarize the points you are replying to (e.g., “In reply to your request for $10,000, absolutely not.”). Also, I think we lean toward top-posting replies because this is what our email clients push us toward, and that has always been the way we replied to written correspondence. (It’s the only way to respond to written correspondence.) Topposting is not the best way to reply to email. Now we are using computers and we have new and better options available to us. In this case it is the inline reply.
Dear Wolfgang, I know you’re busy but please give me a quick reply. Can I borrow $10,000 and is it okay if I tell Thelma about that medical condition of yours? Sincerely, Meriweather
Wolfgang gets the email and responds. Meriweather, Yes and absolutely not. Wolfgang
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Imagine taking a written letter, cutting it into pieces, glueing it on a piece of paper, and writing your replies to specific questions below the relevant portions of the glued-on written letter. Computers make this possible (and easy). These are called inline replies. Inline replies remove the possibility of misinterpretation. As the name implies, inline replies take place right inside the text of the original message where you leave the original email text and reply under the relevant portions of the original message. Wolfgang’s inline reply is in the sidebar. If you take the time to write inline replies, your correspondent will always know exactly what you are talking about. Unless I’m replying to a very simple email, I always do inline replies. The longer the email you are responding to, the more sense this makes. With all of the email clients recommended in this book, creating an inline reply is not difficult. Start a reply and type your greeting at the top (e.g., To my deadbeat friend Meriweather). Then insert carriage returns inside the source email text where you want to reply. The end result is a very clear email that your 56
A Sample Inline Reply Meriweather, > I know you’re busy but please
> give me a quick reply. Can I
> borrow $10,000 Absolutely not. > is it okay if I tell Thelma about
> that medical condition of
>yours? Yes. Sincerely, Wolfgang
2. PRUNE THE EMAIL THREAD.
correspondents will appreciate. It takes a few seconds more to create than a topposting reply (Seconds!) and makes your reply much clearer to its recipient.
Nobody likes receiving an email that includes a thread of 20 prior emails and responses. Nobody is going to read it and they won’t appreciate all the word noise you are throwing their way. Prune old emails out of your reply. Most applications make it relatively easy to select big chunks of text. Rarely can I justify keeping more than two or three prior emails when responding to a thread. Delete everything you don’t need and send a nice, concise, tight response.
BEST PRACTICES FOR EMAIL REPLIES There are some rules of thumb that make a lot of sense for writing email replies: 1. RESPECT THE RECIPIENT’S TIME. Whoever is on the receiving end of the email has no control over what you are about to send. Respect the recipient’s time by thinking through your response and writing a tight, short email. Spending a little bit of your time to save a lot of your recipient’s time should be the rule.
3. NO OPEN-ENDED QUESTIONS. Ask detailed questions enabling your recipient to give a detailed answer. “Do you want the ball bearings made of unobtanium or dilithium?” Whenever you send an email with an open-ended question at the end such 57
as “Thoughts?” or “Ideas?”, a puppy dies. Please don’t kill puppies. 4. DON’T SHOUT! DON’T YOU HATE IT WHEN SOMEONE WRITES TO YOU IN ALL CAPS? DOESN’T IT FEEL LIKE SHOUTING? WHAT’S EVEN WORSE IS WHEN THEY decide to selectively leave portions of the email in lower case and then GO ALL CAPS WITHOUT WARNING TO EVEN FURTHER CREATE THE SENSATION OF GETTING YELLED AT. I hate that.
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EMAIL SIGNATURES
McSweeney’s did an essay on lawyers’ email signatures that is absolutely worth clicking out of this book to read (website). My favorite line explains, “This disclaimer is not unlike the ceaseless blaring of a distant car alarm—a oncesincere warning that has evolved into an unpleasant nuisance, rendered meaningless by its own ubiquity.” Sometimes email signature gibberish is required. For instance, some people in the financial services industry are often required to do it. However, the vast majority of us are not required to do so and shouldn’t.
Signatures are another opportunity to abuse your readers. As a lawyer, I frequently get emails from other lawyers where the signature block is larger than the text they are sending me. In their signature, they will include paragraphs and paragraphs of text about what to do if the email gets lost and explaining how important they are. They’ll even list their email address since, apparently, I wouldn’t have the common sense to look at the top of the email if I wanted to find their email address. Then they add two or three pretty graphics that I don’t care anything about but may mislead me to think there are some attachments of relevance, leaving me to click on them only to see a very lackluster law firm logo.
Signatures should be as simple as possible. Don’t add any fancy graphics that require the recipient to wonder if you’ve attached something important or just an asinine logo, and don’t go crazy with typography either. I 59
keep my signatures largely in plain text and just a couple lines. My usual signature for my lawyer job lists my name, my firm’s name, and my phone number. That’s it:
like you spent more time crafting your signature than the response. I insert my email signatures, when I use them, using TextExpander (website). There are several ways to build in email signatures on the various Mac and iOS applications covered in this book and I will explain them later. The point of this discussion is that you start thinking about using simple signatures that don’t subject you to ridicule.
David Sparks
Finch & Sparks
123-456-7890
I don’t use a canned signature for personal email correspondence. Instead, I usually write David. Rarely, I use an email signature for my MacSparky correspondence that lists my website and calls me an “author” and “broadcaster”, which makes me feel really cool. If I want to feel cryptic, I’ll just write D. The point is to keep it simple. Don’t add graphics, and just give the key information so when you send an email, it doesn’t look
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AUTOMATED REPLIES
An Away Message with Too Much Information
A lot of email clients provide a system for you to send automated replies. Usually found in an email clients’ Settings tab under vacation responders or vacation replies, this is often used for vacation messages.
Hello, I am going to take a three-hour tour on a small boat with a bizarre group of travelers, a confused captain, and his scatter-brained first mate. I shouldn’t be long. Unless the weather starts getting rough and things go horribly wrong, I’ll reply tomorrow. In the meantime, you can contact Jenny at my office at 123-867-5309. Your pal, The Prof.
The problem with the above sample is that it gives way too much detail about what the Prof. is doing. A professional work message 61
CONSIDER THE NECESSITY OF REPLY
simply says you are “away” or “out of town”. I’m not against away messages; they give immediate feedback to the correspondent and let them know when you’ll be back.
A lot of email doesn’t need a reply. If someone writes you,“Thanks”, leave it at that. Don’t write back, “Thanks for saying thanks.” That just embarrasses everyone involved. “Great” and “Awesome” are also frequent offenders. Any time you find yourself writing a one or two word email that isn’t “Yes” or “No”, ask yourself if it is really necessary.
I’ve also seen some people use autoresponders to broadcast the general status of their life. It will say they are very busy and they typically don’t answer email for at least a week. “Hey everybody. I suck and it takes me 6.2 weeks to answer email. Peace out.” On one hand, I see this as really responsible way to communicate expectations. On the other, it always leaves me feeling a bit put off when these messages bounce back at me. Maybe it is because I don’t get offended when people take a long time to respond to me in the first place.
MOVING FORWARD With all of these tactical concepts in mind, let’s now roll up our sleeves and dive into the technical side of email. Put simply, it’s time for you to become the boss of your email.
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CHAPTER 3
HOW EMAIL WORKS
SECTION 1
Why You Should Read This Chapter Email, by its nature, requires the Internet. As users, it is easy to lose sight of this. We think of email as a thing that is on our computers or on our phones but in reality our phones, tablets, and computers more likely only have an image of that email that actually exists somewhere out there on the Internet. Understanding this fact is
critical as an email power user because this simultaneously explains some of emails’ limitations and provides us users a vector to game the system and get better at email. So as much as you want to skip this chapter— don’t. Not only are you about to learn how email works, I’m going to point you to some services that take advantage of email technologies that will change your game. So let’s stop for a moment to talk about underlying email technologies and how the Internet robots think about your email.
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SECTION 2
Email Protocols POP MAIL
POP
For the Internet pioneers, figuring out how to send mail using a computer was actually pretty tricky and, of course, everyone did not agree on the best way to go about it. One of the first standards for handling email was the Post Office Protocol (POP)(Wikipedia). POP was born in 1984. Think about it for a moment. Ronald Reagan was the U.S. president, The Terminator was a new movie, and the POP email premiered. Back in those days, it was unlikely a person would have
more than one computer, and this was reflected in the basic POP architecture.
POP, in essence, is a dummy one-way connection from a mail server to your computer. A POP mail server gets a new mail message from somewhere else on the Internet and waits for you to log in. When you do, the POP sender licks the virtual envelope and pushes the email down to your computer, emptying its virtual mailbag into your computer. The email then resides on your computer for you to read, process, and store. In a lot of ways, the POP
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email protocol is the most similar to the way paper mail is delivered in the physical world. The Internet is a virtual delivery
person. The message is received, then the message is delivered. (I know this is a simplification, but stay with me.)
Screencast 3.1 How POP Email Works
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For a lot of people POP mail worked just fine for a long time. Things, however, got more complicated when people began using more than one computer to read email. This was initially a problem for corporate types who had a computer on their desk and a laptop for the road. The problem began spreading to everyone else with the arrival of smartphones, cheap laptops, and other connected devices. Suddenly, the issues inherent in POP’s delivery system became obvious to everyone.
as the server was concerned, it handled that email when it was delivered to your desktop Mac, and the server was done with it. This made computer users a little crazy. So in response, network administrators flipped a switch on the POP servers that kept the original email message on the POP server. So, returning to the analogy, the mailperson put a copy of the mail in your inbox and kept the original. This way, when you logged on with your phone or laptop, the message was still on the server and was delivered again. The problem is that the virtual POP mailperson wasn’t very smart and he would not remember he already delivered the message once or even know what you did with it.
Put simply, we all had more than one mailbox. POP would deliver a message to our desktop Mac mailbox, emptying its virtual mailbag, and when we logged on with our laptops and phones looking for that important email we knew we saw on the desktop computer, the POP delivery robot said, “Sorry. Nothing here. Empty.” As far
This “fix” created its own set of problems. Because the POP standard was always 67
intended to be unidirectional in its mail delivery, the server had no idea what you did with that message after it was delivered. So if you first received the message on your Mac and filed or deleted it, the server had no idea. The next time you logged in with your laptop, the exact same messages arrived in your inbox all over again. Users found themselves deleting the same spam email multiple times. They also had to file email multiple times and, of course, in no time at all they had different versions of their email library on each of their computers and hijinks ensued. If this story sounds familiar to you, you’re probably using a POP mail service.
more. Most email service providers have moved on. The only places I routinely find POP mail services today are those free accounts you get from Internet Service Providers (ISPs). Cable companies, for instance, still often give their users POP mail accounts. The answer to all the problems POP mail creates is a different email standard that can talk back and forth between the server and your email clients, so when you delete or file a message on one computer, it happens everywhere else. Enter IMAP.
POP mail used to be the standard. Most people had a POP mail account and one computer, and they were blissfully ignorant of POP mail’s failings. That’s not so true any 68
IMAP MAIL
in the bill drawer, so does he. Creepy, right? IMAP talks with your mail applications and keeps track of what is going on with your mail. Indeed, what is really happening with IMAP is your email never leaves the server and those local emails on your phones, iPads, and Macs are just mirroring the IMAP mail. The truth, as they say, is in the cloud. When you delete a piece of spam mail on your computer, the IMAP server takes note and deletes the spam mail on your server. Then when your iPhone later checks in, the server says, “Hey, I’ve deleted that spam message,” to which your iPhone responds with the digital equivalent of “okey-dokey” and deletes the same message from its inbox. This way, your mail is always in sync everywhere. As a result, IMAP always knows what emails you’ve
IMAP
There’s actually some dispute over exactly what IMAP stands for. The acronym is most commonly used to stand for Internet Message Access Protocol so let’s stick with that. IMAP (Wikipedia) introduces two-way communication to the mix, allowing your mail server and the mail client on your computer/tablet/phone to talk to one another. IMAP, which first appeared in 1988, is no late bloomer in the email services game. Returning to the real world analogy, imagine IMAP as a creepy mailperson. He delivers your mail and keeps a copy of everything he delivers. He then peeks through your window and if you throw away junk mail, so does he. If you put a bill
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Screencast 3.2 How IMAP Email Works
read, replied to, filed, and otherwise dealt with and shares that information with every connected email device. When you open that letter on your Mac from your second cousin asking for money to buy a new sump pump,
it will already appear as read when you open your mail application on your iPad. IMAP also tracks and syncs email folders. When you create a folder on your Mac or iPad, it populates up to the server and then down to your other devices. Have you ever 70
created a folder on your Mac to see it later magically appear on your iPhone? If so, you probably have an IMAP server. These synced folders make it possible to use many of the tricks, such as use of the Action and Archive folders, covered in the Tactical Email chapter.
One of my favorite geeky little pleasures is watching my email client send off 42 emails after landing from a long flight. I imagine these little folded electronic paper airplanes firing off in all directions to my correspondents all over the world like something out of Harry Potter and it makes me happy. (I am such a nerd.)
Just because IMAP is a server-based solution doesn’t mean you don’t have local copies of your emails. All of my Macs have copies of all of my email. My iOS devices don’t have all of my email because they don’t have adequate space to hold it all but they do have my most recent email stored locally. Regardless, because I’ve got local copies, email largely works even when I’m off the Internet. The next time I connect to the IMAP server, it checks all the offline activity and syncs everything up, including sending held messages from my outbox.
POP mail has some advantages. It doesn’t use as much bandwidth (since it only talks one way) and if you are freaked out about the way IMAP keeps your messages on a server out there somewhere, POP lets you download all email to your computer to satisfy that growing sense of paranoia. In my opinion, however, these advantages are greatly outweighed by the monumental pain in the neck that comes with a POP account if you own more than one Internetconnected thing. 71
Many of today’s current email services are based on IMAP. The Internet is full of companies that will, for a fee, sell you an IMAP-based email account. (I pay for IMAP email on my MacSparky.com domain from Hover.com [website].) Apple’s iCloud mail and Yahoo mail are also IMAP mail services. Unfortunately, not all IMAP service providers use the same implementation of IMAP. After all, the standard has been around since 1988, and there are a quite a few iterations lying about. Quite often, this is another instance of getting what you pay for. The free IMAP you get from an ISP is usually a lot rougher around the edges than one you pay for. Personally, I’ve been happy with Hover’s implementation and use that for my MacSparky accounts. Another IMAP service provider worth checking out is FastMail (website). While Gmail supports
IMAP, it really isn’t IMAP. (I’m going to explain Gmail next.) Also, except for a few apps designed specifically around Gmail, I’m not aware of any currently developed mail application that does not support IMAP mail. One of the advantages of an IMAP mail service is that because the mail is stored on a server, you can offload some of the work of sorting and organizing that email to Internet robots. In the last few years, we’ve seen some very sophisticated services that will predictively organize your email into folders for you. There are two that I think are worthy of recommendation: Sanebox and AwayFind. I rely on these services to avoid E. B. White’s despair and will be explaining them at length later in this chapter.
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GMAIL
lot of times it actually is a good thing. You can go overboard with it, though. Adding labels to emails takes time. If you deal with a lot of email, that time stacks up pretty quickly.
Gmail is an outlier in all of this. Gmail supports both POP and IMAP protocols, but at the same time Gmail is neither POP nor IMAP. Gmail organizes email with tags (called labels). You can place multiple labels on a single email letting you organize by several criteria. For example, I could label an email “Eddie Smith”, “friend”, “plunger”, and “money owed”. I could then search for all emails that contain the labels “friend” and “money owed” and this email would appear. Using IMAP, you can’t place an email in more than one folder so there is only really one dimension of organization. Labels give you as many dimensions as you please. That seems like a good thing, and a
The big takeaway for Gmail (at least with respect to discussing the underlying technologies) is that because it really isn’t POP or IMAP, traditional mail applications sometimes have fits dealing with Gmail. Some clients deal with multiple labels on Gmail by making multiple copies of the message and creating a separate folder for each tag. Crazy. If you use Gmail a lot, I’m going to recommend you use Gmail’s own web interface or one of the applications built exclusively for managing Gmail. Gmail gets its own chapter in this book, chapter 5, so you’ll get all the nitty-gritty soon enough.
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I CLOUD
EMAIL
devices such as Android phones and Windows computers.
iCloud (website) is the name Apple applies to a whole bunch of different web and cloud-based services. One of those is iCloud mail. iCloud accounts are free when you buy an Apple device, but as you use iCloud more, you may need to buy additional storage from Apple.
As IMAP mail services go, iCloud is pretty good. For the last few years Apple has been investing heavily in server farms, and iCloud Mail is becoming increasingly reliable. Because it is an Apple product, it is tightly integrated in the OS X for Mac and iOS operating systems and is easy to set up. In addition to specific email clients, you can access your iCloud email account from any web browser at iCloud.com. Apple’s web portal to email is remarkably Apple. It doesn’t have the utilitarian look (or amazing keyboard shortcuts) you get with Gmail, but it looks great and has a lot of nice little touches that make it feel more like an independent application than a web page.
For the purposes of this book, I’m just going to to talk about iCloud Mail, which is Apple’s version of an IMAP mail service. You don’t have to use Apple’s mail client to access iCloud Mail. It works on any email client that supports IMAP, which is pretty much all of them. You could even access and use your iCloud email account on non-Apple
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Gallery 3.1 shows email management at iCloud.com.
Gallery 3.1 Using iCloud in the Web
to an email of your choice. These rules are applied on the iCloud also has iCloud.com the ability to servers so the apply server-side emails get rules. I’m going to managed even if explain email all of your rules in depth computers and later in this book mobile devices are in chapter 4. turned off. (This Email rules let Start by logging in at iCloud.com is in contrast to you automatically the Apple Mail perform actions application rules on email matching that are much certain criteria. more robust but iCloud.com’s implementation lets you look also require a running Mac, which is also for emails with particular senders, covered in Chapter 4.) recipients, or subject matters and trashes or files those emails for you, or forwards them 75
Recently, Apple has come under criticism about the way the iCloud Mail services filter spam. Specifically, Apple can sometimes get too aggressive with spam filtering and messages that should be delivered aren’t getting delivered. In 2013, Macworld magazine explained this in an article (website) where the authors, by including the term “barely legal teens”, were unable to get messages to one another even though they were not the kinds of messages those words imply. I’ve been using the Apple Mail service for years for my personal account and I’ve been happy with it. Since I spend so much time working on Apple devices, having an iCloud email account is really convenient.
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MICROSOFT EXCHANGE
solutions. That is no longer true. Now OS X for Mac and iOS both natively support Microsoft Exchange. Indeed, in my experience my iPad and iPhone support Microsoft Exchange better than the Windows 7 computer sitting sadly in the corner of my office. You can easily access Microsoft Exchange with the native Apple Mail clients. Microsoft also has a version of its email/calendar/contact/task application, Outlook for the Mac, which is covered in chapter 6.
Microsoft has its own mail and messaging protocol for Microsoft Exchange. Exchange is one of the most common solutions for syncing up mail, contacts, calendars, and tasks in companies. The mail component works a lot like IMAP but also differs with respect to the specifics. While I know lots of people who use Microsoft Exchange technologies at their work (indeed, I use it at my day job), I don’t know anyone that uses it for their personal account. For a long time, Microsoft Exchange email meant you were limited on your options for accessing your email to Microsoft-specific 77
THE CASE FOR OWNING YOUR OWN EMAIL DOMAIN
Apple’s iCloud Mail. Those accounts aren’t dependent on where you live or who you pay for that copper wire leading into your secret lair. However, some emails can feel like a stigma. When I see someone with an AOL address, for instance, I don’t expect them to be very computer savvy.
While on the topic of email technologies, I’d urge you to consider the idea of owning your own email address. So often, people’s email is based on their Internet Service Provider (ISP) (e.g.,
[email protected]). I get why people start these emails: they are easy and free. However, these ISP emails are usually the worst when it comes to service. They also often default to the POP standard, and they are not mobile. If you pack up and move to a different town with a different cable or DSL provider, you’ve got to get a new lousy free email account and get word out to your friends and family that the old one no longer works.
If you really want to do this right, take the extra step of setting your email to your own domain. It is not that expensive to buy a domain, such as
[email protected]. Then you could set up an email at your own domain, such as
[email protected]. That way you’ve got an email address that truly is yours—for life. To register a domain costs about $10 per year. You’ll also need to get an email hosting service, which is offered by many domain name server companies.
It makes a lot more sense to set up your own portable email. You could do this with an email provider such as Google’s Gmail or 78
When my daughters were born I immediately registered their domains. Now they are teenagers and the domains are still parked but I’m sure they’ll want them at some point. The nice thing about owning your own email through your own domain is that it is uniquely you and lets you avoid hitching your email address to someone else’s product.
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SECTION 3
Common Email Account Settings EMAIL PASSWORD
No matter what email vendor you use, there is a good chance that at some point you’re going to need your account details to set up an email client or troubleshoot a problem. Here’s the skinny.
Make sure to keep your email password somewhere safe. A spreadsheet document on your desktop labelled “Passwords” is not safe. I use 1Password (iOS App Store) (Mac App Store) (website). There are other options depending on which platform you’re on. I write a lot more about email passwords in chapter 8.
EMAIL ADDRESS I’m a big fan of simple email addresses. Mine is
[email protected]. Email addresses such as
[email protected] and
[email protected] seem like a great idea right up until that point you need to give your email to a prospective employer or new client. Keep it simple. 80
FULL NAME
email address (e.g.,
[email protected]) but sometimes it’s the name without the email address (e.g., david). A few years ago it was the username on the account (which might be something such as davids42148) with the mail server when you signed up for the service and not your email name. This practice led to much rending of garments and, as far as I can tell, none of the major email providers do this anymore. If your mail service doesn’t provide you any guidance, start with the email address. That’s usually the answer.
Use your full name. For example, David Sparks, or better yet, Sir Pincus Redbottum III, Esq. DESCRIPTION When setting up an email account in your email client, you’re often asked for an account description. If you have multiple accounts, this helps keep your head on straight. For example, you could describe your Microsoft Exchange account as “Work” and your iCloud account as “Home”.
INCOMING MAIL SERVER This is the mail server that throws email at you. Usually it is very simple, such as mail.hover.com or imap.mailserver.com. If you’re feeling lucky, try using mail or imap along with the name of your server (e.g.,
USERNAME Often account setup will prompt for a username. This is the name attached to the user on the mail server. It is usually your 81
mailserver.com). If that doesn’t work, do an Internet search with something such as “mail settings for [insert service] mail account” and you’ll find what you need pretty quickly. The mail server settings always throw people off. Once you figure it out, write it down somewhere. (This is another thing I do in 1Password.)
1Password’s Email Settings Screen
OUTGOING MAIL SERVER This is like the incoming mail server. Indeed, with some services they use the 82
identical server. Others use a slightly different server, such as smtp.mailserver.com. (SMTP stands for Simple Mail Transfer Protocol.) Again, a web search or call to your mail server’s customer support should set you right. Several of the better mail server companies even have step-by-step screenshots showing you how to enter these credentials with all of the major email clients.
SSL
coffee shop’s wireless router in that transparent envelope. It didn’t take long for crooks to figure this out, and now there will routinely be some reprobate in the corner monitoring the traffic, looking for someone broadcasting their email “in the clear” (which is nerd speak for unencrypted). Once they get your email username and password, then they log into your email and all hell breaks loose. Don’t believe me? Think about all the emails you have with account details, credit card transactions, banking information, and other details of your life you’d rather keep on the down-low. The concept freaks me out so much that I almost always prefer to use the Internet connection from my iPhone or iPad even when there is free WiFi.
When the IMAP and POP protocols were first created, nobody thought much about security. Moreover, nobody was thinking about things such as WiFi and wireless communications. As a result, they didn’t build any encryption into email. When you sent an email message, it was wide open for anyone to read as it made its way through the Internet. It was like sending letters with transparent envelopes. This problem was mitigated by the Internet Service Providers that have been systematically upgrading the security of your data once you put it in their hands. The real trouble started with WiFi. When you go to the coffee shop and suck down your triple shot latte while answering email, you are sending mail, usernames, and sometimes even passwords from your computer to the
SSL (Secure Sockets Layer) is a bit of magic that encrypts that data over the air so 83
nobody else can see it. You’ll see this on your banking and other e-commerce sites. It also works on your email and you should always turn it on. It is a method by which your normal “in the clear” information is wrapped up inside an encrypted envelope. SSL is employed on the web to secure ecommerce and banking websites, and it does much the same for your email.
POP
IMAP
SMTP
Standard
110
143
25 or 2525
Secured
995
993
465
(SMTP is a separate email protocol used for moving email around the Internet.) The point here is that if you are prompted for a port, the above should work. If they don’t, contact your email provider for the details.
PORTS Sometimes email configurations will ask you to list a port. This is not making reference to Portuguese wine but something more akin to a shipping port with berths for all the incoming and outgoing Internet data. A few ports were set aside for email. These are the most commonly used email ports:
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SECTION 4
Third-Party Mail Services
A common theme emerging through this discussion is that all modern email protocols involve keeping a copy of your emails at Google, Microsoft, iCloud, or some other server. There are a few implications to this. One involves security and privacy, which is explained later in chapter 8, but
another involves convenience. It is so convenient having your email sync everywhere. It didn’t take long for people to start thinking about the fact that if their email was in the cloud, perhaps the cloud could manage their email for them while they were busy doing other things, such as building LEGO sets with their
85
children. A couple of noteworthy services doing this are SaneBox and AwayFind.
respond to? Which were filed? Which were immediately deleted? You can also have SaneBox look at your Twitter, Facebook, and LinkedIn contacts so that it has a better idea of who is important to you. SaneBox does not read the contents of your email. Instead SaneBox looks at the message headers, the senders, dates, and what you did with it. Nobody (and no computer) at SaneBox reads your mail. This point was so important to me that I called and asked before signing up. SaneBox then uses that information about what you did with your email in the past to help automate what SaneBox will do with your email in the future.
SANEBOX SaneBox (website) is a service that monitors your email accounts. It works with IMAP, Gmail, and even Microsoft Exchange accounts. SaneBox will monitor your email account and act on your email for you. I like to think of it as my own personal email robot ready to do battle with all of those other email robots out there trying to take my precious time. This is a fee-based service. When you first sign up, SaneBox looks through your email to see what you did with it: Which emails did you 86
EMAIL FILTERING
SaneBox has picked up my instruction here and normally puts those types of email messages in the News folder. The advantage of this is that I can deal with critical email from my email inbox, put off less critical mail in the Later folder until I have more time, and decide—much later—if I’ll go through the News folder or delete it in bulk. SaneBox also sends me an email (I appreciate the irony here) that summarizes everything it sorted for me so I can make sure it is not screwing up. If it does make a mistake, such as putting an important email in the Later folder, I can manually move it back to the inbox, and SaneBox will notice and self-correct next time.
SaneBox’s banner feature is email filtering. Specifically, it analyzes each new email based on your past interactions with your inbox. It leaves the most important messages in your inbox and moves all others out into folders you create with your SaneBox account. For example, I have several SaneBox folders on my MacSparky.com email account. One is called “Later”. SaneBox puts emails in the Later mailbox that are not from key people in my life. When I look at my email in the morning, the MacSparky account may have two or three messages in the inbox and the Later folder may have 20 or 30. I’ve also got a SaneBox folder on that account called “News”, in which I’ve pushed marketing and newsletter-type emails. Again
SaneBox’s ability to determine the appropriate folder for an incoming email is uncanny. SaneBox does a fantastic job of predicting where I want an email to go and 87
putting it there. Within a few days of signing up for the service, I quickly began to rely upon it. When it does make a mistake and I move an email from the one SaneBox to another, SaneBox remembers that the next time I receive an email from that person. I was so impressed with SaneBox that I called and asked how they did it. They explained that their servers aren’t just looking at whom the email comes from but also how I respond. An email that I open immediately implies more priority than one that I don’t. Emails that I respond to are more important than emails I delete. There is a lot to how SaneBox works.
email. It does, however, have your email login and password, which is required to observe what you’re doing with your email. I spoke with representatives from SaneBox about this and they explained that the email access data is on a nonpublic server and held very securely. They further explained that their employees don’t have access to your email. At the end of the day, to get a service this useful you’re going to have to give the server email access. There simply is no other way. This is one of those convenience versus security questions that each person has to answer for themselves. In my case, I decided to use SaneBox for my personal and MacSparky accounts but don’t use it with my day job lawyer account.
A legitimate concern about using services such as SaneBox is the protection of your email privacy. In order to work, SaneBox needs to have access to your inbox. SaneBox never looks at the body of your 88
Regardless, this service really works and is tremendously helpful in separating the wheat from the chaff. Think about this for moment: How much would you pay someone to check mail 24/7 and perform this initial sort for you? It’s like magic. This alone is worth the price of admission for SaneBox and there are additional features.
your email database, this gives you an easy place to find all received email attachments. THE BLACK HOLE One of the stock SaneBox folders is ominously named SaneBlackHole. I explain later in chapter 7 why spam is such a problem and why unsubscribing doesn’t always work. Indeed, in some cases unsubscribing merely confirms that there is a human at your email address and the crooks then send even more spam. If you drop an email into the SaneBlackHole folder, SaneBox will monitor all future emails and capture anything similar in the future. It is a user-controlled unsubscribe button. This doesn’t just work for people selling you Viagra either. There are some people in my life that have earned their way into the Black Hole.
CLOUD ATTACHMENTS Another common email gripe is the way attachment files clog up your email database. SaneBox attempts to solve this by letting you attach your email account to your Dropbox (website), Box (website), or IBM SmartCloud (website) and automatically routing your incoming email attachments to your cloud storage. In addition to helping keep down the size of
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EMAIL REMINDERS
and then pass the potato back over to them. A challenge for you is to then remember to check back on the project later if they don’t respond. SaneBox allows you to add reminders to outgoing email.
A lot of times email exchanges are like a game of hot potato. Somebody may ask you to do something on a project. You’ll do it
Screencast 3.3 Configuring and Using SaneBox
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If you send an email to your coworker and copy (or blind copy) the email to
[email protected], in one week SaneBox will throw the email back at you (unless you have received a response from that person). It is all really clever. It doesn’t just have to be one week. It could also be
[email protected] or
[email protected].
folders will disappear from your inbox until the designated time. You can also set up a custom folder with a different defer date. While I was initially skeptical about the wisdom of deferring email, I’ve come around to appreciate it as I wrote this book. There is some email that can wait until tomorrow, or Saturday, or next week and getting it off your plate by deferring it is a good way to make that happen.
Instead of replying to your coworker you could also forward the email to
[email protected] and then SaneBox will resend you the email at that time.
If you are dealing with a large volume of email, SaneBox can be some of the best money you spend to help manage the onslaught for you. I will explain my personal email workflow at the end of this book in chapter 10 but for now I can tell you SaneBox is a critical component to that.
DEFERRING EMAIL SaneBox has a mechanism for deferring email through mail folders. By default it has @SaneTomorrow and @SaneNextWeek folders. Any email you copy into those 91
Can you tell I’m pretty smitten with SaneBox? Screencast 3.3 explains some of SaneBox’s best features.
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AWAYFIND
to someone’s email within minutes, it will recommend adding them to the list.
AwayFind (website) attempts to settle the problem of email notifications. I have already explained my disdain for email notifications. Nevertheless, there are some people for whom you will want notifications. Perhaps you have a boss that expects you to reply to emails within 10 minutes or a client project for which you absolutely must know as soon as an email arrives. Rather than constantly checking your email for these key people or events, AwayFind checks your email for you and notifies you when you receive an email from a specific person or concerning a specific subject.
AwayFind will also look for emails on a particular topic. You create these by providing AwayFind keywords that you want it to look for. For instance, if you add the words sales proposal to an AwayFind search, any email matching that criterion will give you an alert. One of the most clever implementations is the ability to look at your calendar and notify you if that person emails you. For instance, if I’m going to meet Brett in the next hour and he sends me an email, AwayFind will send me a notification regardless of whether I designated him as a person to follow.
AwayFind even looks at your email history to help you decide which people are important to you. If you routinely respond 93
There are several methods for AwayFind to notify you. You can receive a text message or be notified through the AwayFind iOS App on your iPhone (iOS App Store). AwayFind is a paid service, though a free plan is available. In my experience, AwayFind works best with Gmail and a Google Apps account. The Gmail integration is great, and many of the AwayFind features and services will appear right in your Gmail window. Apple now has a similar service with VIPs (covered in chapter 4), but they are not as smart as AwayFind. VIPs focus on people and not on subject matters or upcoming appointments. Also, you can’t set VIPs to autoterminate like AwayFind can. Now that you’ve wrapped your head around how email works, let’s put this to practice with some of the most popular mail applications and services available for the Mac, iPad, and iPhone, starting with Apple Mail.
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The AwayFind iPhone App
CHAPTER 4
APPLE MAIL
SECTION 1
Apple Mail For the longest time, there was a real shooting war between rival email client applications. Several companies actively developed email software and, as customers, we had many options to choose from. That ended when the companies that shipped the operating systems started to include their own email clients. For
the Mac, it was Apple’s Mail application (or app), and for Windows, it was Microsoft’s Outlook Express. When consumers started getting email clients with their operating systems that met most of their needs, they were much less likely to shell out money for an independently developed email client. While this appears to be changing 96
(and I’m covering some competing mail applications in chapter 6), Apple Mail is still the most frequently used mail client on the Mac, iPhone, and iPad.
operating system in ways that competing clients simply can’t match. So let’s dig in and I’ll show you how to get the most from Apple Mail.
In my first draft of this book I equated Apple Mail to vanilla ice cream. In later drafts, I explained how recent updates added chocolate chips. However, as I finish this book, it occurs to me that Apple Mail has become quite powerful including specialized tools, keyboard shortcuts, automation, and multi-platform features (like VIP) that most email clients can’t touch. We’ve come a long way from vanilla ice cream. I am an email power user and I use Apple Mail every day. On the Mac side, Apple Mail plays nicely with third-party plug-ins, which can dramatically improve Apple Mail’s functionality. Also, because it is Apple’s Mail application, it is tied into the 97
APPLE MAIL OVERVIEW
increase its functionality. Also, the Mac doesn’t use the same one-app-at-a-time paradigm that the iPad and iPhone do, making it easier to share data out of Apple Mail on the Mac.
Apple Mail seeks to provide the user a common features set and email paradigm across all Apple devices. If you use Macs, iPads, and iPhones, this is convenient. Some of the features covered in this chapter just work across all of these platforms and can be a useful tool in your arsenal. There are, however, differences between the platforms.
The iPad version of Apple Mail loses the plug-in support and keyboard shortcuts that come with Apple Mail but still does a good job of presenting a lot of data regarding your email. I often process email on my iPad. I find the Retina display, onscreen keyboard, and easy portability to be the right fit to let me manage email just about anywhere.
The Mac version provides the most traditional email experience. It takes advantage of your computer screen to show you the most data. It also takes advantage of Mac’s keyboard and mouse to include some useful user interface mechanisms, such as keyboard shortcuts, to help you make quick work of your email. Another advantage of Apple Mail on the Mac is support for AppleScript (the Mac’s scripting language) and the ability to add plug-ins to further
The iPhone version of Apple Mail is, in my mind, all about processing my inbox. Much of the Apple Mail user interface on the iPhone is designed around reading, filing, and quickly responding to email on your 98
phone. I find the iPhone works great for clearing out an inbox, but it’s not my first choice for writing email of any significant length. That’s me. I know people who are comfortable writing long passages with the iPhone keyboard. For them the iPhone is where they manage most of their email. The point is every iteration of Apple Mail is a little different, and Apple Mail attempts to take advantage of the platform it was designed for.
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SECTION 2
Setting Up Your Accounts SETTING UP ON THE MAC
We used to have just one email account and one computer. Now we’ve got multiple email accounts, multiple computers, and multiple other iThingies that go in our pockets and bags. Setting up your email account—if you’re not used to these things—can seem daunting but it’s not. Anyone can do it in Apple Mail.
On your Mac, you set up new mail accounts in the Mail application or through Internet Accounts in System Preferences. After launching System Preferences and clicking Internet Accounts (under Internet & Wireless), you’ll see the left pane displays existing accounts while the 100
right pane displays services to set up new accounts. These preconfigured services include iCloud, Microsoft Exchange, Gmail, Yahoo, and even AOL. (There are other services listed in this menu unrelated to email including Twitter, Facebook, Vimeo, and Flickr.) If, for instance, you want to set up an iCloud account, click on the iCloud icon in the right pane and then System Preferences will walk you through the setup. You can forget all about ports, IMAP server addresses, and all the other details I explained in the previous chapter. When using these most common services, all you need is your email address and password. Apple Mail does the rest and your account is set up.
Gallery 4.1 Apple Mail Setup Screens on the Mac
Here is the Internet Accounts System Preferences on the Mac in 10.9 Mavericks.
However, Apple’s list of preconfigured email services is not exhaustive. There are a lot of email providers that didn’t get one of 101
Apple’s magic buttons. For those, you’ll need to enter your email credentials manually. Do that by clicking the Add Other Account... button. The application walks you through a series of dialog boxes, shown in gallery 4.1, which prompts you for the details of your email account. I explain those details in chapter 3. If you don’t have all the details, a quick Internet search or phone call to your service provider should get you set up. I keep notes on all my email accounts in 1Password (iOS App Store) (Mac App Store) (website) so when setting up a machine, I’ve got everything I need. Once you get to the end of the dialog boxes, Apple Mail will see your new email account, and you can get back to work.
Screencast 4.1 Setting Up Your Email Accounts on the Mac
email accounts on the Mac from inside Apple Mail by clicking Mail on the Mail menu bar and clicking Add Account… or Preferences.... Click on the Accounts tab and then the plus sign (+) at the bottom-left portion of the dialog box. This opens a series of dialog questions very similar to those found from the System Preferences screen explained earlier. In fact, once you’re done setting up the email account, that
You can also set up new 102
SETTING UP ON THE IPAD AND IPHONE
account will show up in System Preferences under Internet Accounts. Screencast 4.1 demonstrates setting up an email account on the Mac.
Managing email accounts on the iPad or iPhone does not take place in the Mail app. Instead, you’ll find the account tools in the Settings app in the Mail, Contacts, Calendars screen. This screen includes several settings and preferences for your mail accounts. For now, just look at the top, which includes a list of accounts. (See gallery 4.2.) Tapping on an existing account slides in a screen with additional options and settings for that account. The iCloud account settings are, not surprisingly, the most extensive since iCloud is an Apple product, and its services reach deep into the Mac and iOS operating systems. Particularly relevant to this book is the Mail switch. If you turn it off, your iCloud mail disappears from Apple Mail. Switching it 103
back on returns it. This on/off function works for all of your installed mail accounts. This can come in handy. For example, when truly on vacation or even just spending an afternoon with my family, I’m not above simply turning some email accounts off.
with iCloud, you’ll be prompted for your Apple ID and password. That’s it. Tap in those two items and you’re set. Often these third-party services will also provide you calendars, contacts, notes, and other services as part of your account. If they do, you’ll be prompted with the account setup to choose which services to turn on. Only turn on those services you plan on using. If, for instance, you love your Gmail account but don’t plan on using Google’s calendar service, turn it off. If you have three calendar services turned on but only use one, you are inevitably going to put an event in one of the dormant calendars, miss your nephew’s Eagle Scout ceremony,
To add a new email account, tap Settings→Mail, Contacts, Calendars→ Add Account.... This opens the Add Account... screen shown in gallery 4.2. For setting up accounts with the most common email providers (including iCloud, Microsoft Exchange, and AOL), you simply need to pick the provider and enter your account details. For example, when setting up an email account 104
have your sister angry at you for six months, and then not get a very good birthday present from her. So as you can see, turning off redundant, unused services always leads to better presents.
“Other”. Tap Other and then tap the Add Mail Account button. Apple then presents you a series of entry boxes with descending levels of nerdiness. The first is the easiest, asking for your If you’ve got an name, then email email account with address, password, This is the first email setup screen, letting you a provider not choose between available services. and an account included on Apple’s description. iOS list, all is not lost. will then try and Similar to the Mac, hook up the there is a mechanism for manual setup. account on that information alone. If it fails Under the list of built-in accounts in the (and it often does), it will take you to Add Account... screen is a button labelled another screen asking for more details. This Gallery 4.2 Apple Mail Setup Screens on the iPad
105
is where all of those account details I covered in chapter 3 come in handy. If you master those, you shouldn’t have any trouble setting up an email account on your iPad or iPhone. Screencast 4.2 Setting Up Email Accounts on the iPad
When you are done, enable your new account and get back to the Mail application to make sure everything is working. Gallery 4.2 shows several screenshots on how to set up new mail accounts on iOS. Screencast 4.2 includes a demonstration of setting up a new mail account on the iPad. As you can see, setting up new email accounts on the Mac and iOS for use in Apple Mail is not difficult. At this point you should be able to set up all the accounts for yourself, your family, and coworkers. That always leads to better presents.
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SECTION 3
Checking Mail CHECKING MAIL ON THE MAC
sticking it to the man, digitally. They won’t see any incoming email while 1 working. A less extreme solution is to let email push to your devices so the messages are there when you go looking for them, but turn off all notifications so you don’t hear the ding every time someone (or some robot) sends you an email.
Apple Mail checks email automatically when you load the application and is set, by default, to accept push notifications. That means if an email service includes the ability to push an email (and notification) to your devices immediately upon delivery, Apple Mail will do so. Alternatively, you can set Apple Mail to check for new mail after a certain time interval or not at all. Telling your email client not to check automatically can make sense. I know some people who turn off all email delivery when they are focused on a project. It’s their own way of
On the Mac, you can adjust how often Apple Mail checks for new email. Click 107
Mail→Preferences...→General→Check for new messages: and choose how frequently you’d like to check for new mail. You can set this for each individual email account.
Apple Mail on the Mac includes a unified inbox. That’s the primary inbox in Mail that combines inboxes from all of your active email accounts. You can also check for specific accounts if that makes more sense for your workflow. On the Mac, if you find yourself frequently accessing a particular inbox—or any email folder for that matter— drag it up to the toolbar. This is a more recent feature in Apple Mail for Mac that allows you to quickly access your most frequently accessed folders. They’re always up in the toolbar, and you can click on them at any time. Even better, you can access each toolbar mail folder with a key combination. To do so, hold down the Command key and press the number key corresponding to the folder on the toolbar. The first folder will be Command+1, the second folder will be Command+2, and so on. For instance, in the screenshot below,
Setting the Email Frequency in Apple Mail
108
The Command Plus Number Trick
Screencast 4.3 Checking Email in Apple Mail and Navigating Mailboxes with Keyboard Shortcuts
Command+3 will jump to the Action folder. I use this feature all the time to move between my mail folders. Screencast 4.3 demonstrates how to check your mail on the Mac and move between email folders.
109
CHECKING MAIL ON IOS The Apple Mail app on your iPhone and iPad checks for new messages automatically by default. It also has the option to change this setting to time intervals or not at all. On the iPhone and iPad, tap Fetch New Data in the Mail, Contacts, Calendars screen, shown in gallery 4.3. On this screen, you can set new data preferences for each mail account. For instance, you could set your Microsoft Exchange account to push mail at you whenever it is received and set your personal email account to only fetch new mail when you specifically request it. Or better yet, the exact opposite of that. It is worth noting that these push settings are done not just by account but also by mailbox. You could, for instance, push your inbox and Action mailbox but leave your Archive mailbox alone. Apple Mail on the iPad and iPhone also has a unified inbox. This wasn’t true with the original release of iOS, and its addition was welcomed by those of us with multiple email addresses. One nice addition with iOS 7 is customization of the mailbox view in iOS Apple Mail. By default, this screen displays the unified inbox along with specific inboxes for each 110
Gallery 4.3 Setting Email Frequency on Apple Mail for the iPhone and iPad
of your email accounts, the VIP mailbox, and flagged messages. However, tapping the Edit button in the top-right corner lets you turn off any mailbox you don’t use. For instance, if flagged messages aren’t your thing, you can turn off the flagged message mailbox. (I so rarely flag messages that I’m tempted to turn it off.)
the Mac (explained later), these preformatted folders are useful. Another nice addition in iOS 7 is the ability to place some of your favorite email mailboxes on this screen. For example, that Action mailbox that I keep yakking about is Screencast 4.4 Checking Email and Setting Up Custom Folders on the iPhone and iPad
You can also turn on additional email boxes that provide different windows into your email. There is an Unread box that displays all unread email from your inboxes. There is another view, labelled “To or CC”, that only shows messages addressed or copied to you directly. There are also options to display all messages with attachments, all draft messages, all sent mail, and all trash. While iOS Apple Mail doesn’t have the Smart Folders you can create with Apple Mail on
111
on this screen on my iPhone. To add a mailbox, tap the Add Mailbox… button in the Edit screen, navigate to the mailbox you want to add, and tap on it. I’ve added several of my most used mailboxes to this list and it makes iOS mail management much easier. Screencast 4.4 demonstrates how to check your mail on the iPhone and iPad, move between email folders, and set up and use custom folders on iOS Apple Mail.
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DATA DETECTORS
Apple Mail Data Detectors in Action
Data detectors are one of the most useful features of Apple Mail. The application is always studying your incoming email for phone numbers, addresses, or calendar items. On the Mac, hover your mouse on the information, or on iOS, tap on it, and Apple Mail presents you options. Phone numbers can get added to existing or new contacts. Apple Mail will also display the phone number in large type across the screen. An address may get added to a contact or displayed in the Maps application (new in OS X Mavericks). Calendar events get added to your calendar. Data detectors also work with shipment tracking numbers such as FedEx and the U.S. Postal Service; clicking on it gives you the option of tracking your package. I use data detectors nearly every day for updating and adding
contacts and calendar events. Screencast 4.5 shows how to work with data detectors.
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SETTING APPLE MAIL NOTIFICATIONS
iPhone give you plenty of control over notifications.
Notifications are a big deal. I talked about this in the Chapter 2 discussion of tactical email. There must be someone at Apple who agrees with me because the most recent versions of Mail on the Mac, iPad, and
NOTIFICATIONS ON THE MAC In Apple Mail on the Mac, click Mail→Preferences...→General→New messages sound:. Set to None and banish the ding from your life. I leave the Play sounds for other mail actions option checked because the whooshing sound of sent mail satisfies something deep within my soul. Turn off Dock unread count: if you’d like, or point it at different Smart Folders. I’m going to explain Smart Folders in detail later in this chapter.
Screencast 4.5 Using Apple Mail Data Detectors
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notification pop on your Mac’s screen every time you start getting some work done? I have the attention span of a puppy and those notifications cause me nothing but trouble. I can be sitting there, working hard on the final equation for a drug to prevent people from using the word literally in every sentence. Then, suddenly, my Mac gives me a notification that I’ve received an email for 30% off yack-herder shoes and I’ve lost it. My miracle cure has literally left my head, and I’m back to the drawing board. I’m sure there are studies, but I don’t need to link them. Everyone reading these words has experienced the loss of concentration that comes with little interruptions. I recommend turning the notifications off entirely.
Gallery 4.4 Mac Email Notification Screenshots
You can turn the message sound off in the General tab of Apple Mail’s preferences.
OS X for Mac now gives users pop-up notifications just like iOS does. It’s a terrible idea. Can you imagine getting an email
Unfortunately, turning off notifications isn’t possible for everyone. Maybe you’ve got a crazy boss that expects you to reply to 115
emails within minutes or a sick relative. In that case, set those people who are important enough to merit your immediate attention as VIPs (covered later in this chapter) or use a service such as AwayFind (covered in chapter 3) and limit notifications to just those people. Respect yourself. Protect your focus and attention.
Screencast 4.6 Setting Email Notifications on the Mac
Gallery 4.4 shows notification screenshots on the Mac and screencast 4.6 walks you through notification setup on the Mac.
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NOTIFICATIONS ON IOS
Email Notification Settings on the iPhone
On your iPad or iPhone, go to the Settings app, tap the Notifications button, and then tap the Mail button to see the Mail notifications. The first setting lets you adjust the number of unread messages to display in the notification screen that appears when you drag down from the top of the screen. You can then set specific notifications in relation to each of your email accounts. Do you want to get badges and notifications from your work account but not your personal account (or the opposite)? Adjust your accounts accordingly. I turn off nearly all of my notifications. There are three types of alerts: (1) Banners, which show up at the top of the screen and fade out after a few seconds; (2) Alerts, which appear in the center of the screen and don’t go away until you tap the screen to dismiss them; and (3) None (my beloved), which gives you no notifications. In this screen, you can also turn off new mail notification sounds and the badge that appears 117
on the mail icon. I really dislike both of these distractions and did my own private happy dance when Apple gave us the option to turn them off. The new email badge on my iPhone is one of those things I am absolutely powerless to resist. Turning it off removes the temptation.
Screencast 4.7 Setting Email Notifications on the iPad
The final two iOS notification-related mail settings let you choose to show a preview of the message in notifications and whether or not notifications show when your iPhone and iPad are locked. I’ll leave these up to you, but be warned: if you have any concern for your email security, letting your device display messages when they are locked probably isn’t a good idea. Screencast 4.7 demonstrates email notification settings on the iPad.
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Filing Email in Apple Mail So let’s say an email lands in your inbox and you deal with it. You and that email are at peace with one another. How are you going to file the email away? There are several ways to do that on the Mac, iPad, and iPhone.
time. It also requires you to lift your hands from the keyboard, which slows you down. Not only that, it entails a very fine mouse gesture. Those folders in your sidebar are not very large, and if you’re not careful, you will drop
FILING EMAIL ON THE MAC The most common method for filing email on the Mac is clicking it with the mouse and dragging it to a destination folder in your sidebar. That is, however, the worst way to file your email. Using the mouse to click and carefully drag to a folder requires extra 119
emails into the wrong folder. In fact, even if you are careful, you will occasionally drop emails into the wrong folders. Even worse, you won’t always notice when you make that mistake. Then later, when you go looking for the email, it will be missing and, at best, you’ll spend even more time hunting for it. If you take an email that you meant to place in your Action folder but accidentally place it in your trash instead, you’ll never respond and look like a flake to somebody.
The Control + Command + Number Trick
system, Apple has added its own keyboard shortcuts to Apple Mail. Remember those keyboard shortcuts I explained above concerning accessing email folders? They also work to move email messages to those folders. Where the Command key and a corresponding number will jump to a folder, Control, Command, and a corresponding number will move the current email to the folder. This makes filing email easy with the keyboard. For instance, you could be in your inbox and see an email from a friend thanking you for buying her a fancy new chainsaw, and you can send it to the Archive
There are better ways to file email on your Mac that are faster and more reliable. Part of becoming an email pro involves mastering these. Until recently, the only way to automate filing email with keyboard shortcuts in Apple Mail required a thirdparty application, such as Mail Act-On (explained later in this chapter). However, with recent versions of the Mac operating 120
by holding down the key combination
Control+Command+4 (assuming your Archive is the fourth folder in your toolbar). There will be no messy mouse clicking and dragging and no potential for putting it in the wrong folder. Best of all, once you master this keyboard shortcut, you will do it automatically. This is how I file email in Apple Mail on my Mac, and it is really fast. It becomes muscle memory and you can zip through your email quickly. Some users even give the mailboxes names mathching their position. (e.g., “1Action”)
archive a message and saves you extra room in your menu bar. Screencast 4.8 demonstrates how to move email messages on the Mac.
Screencast 4.8 Filing Email on the Mac
Another great keyboard shortcut is Control +Command+A, which will 121
FILING EMAIL ON IOS
Filing an Email on the iPhone
Filing email on your iPhone or iPad requires manipulation of the touch screen. This is different from keyboard shortcuts and probably a bit slower but also more reliable than using the mouse on the Mac. Simply, there are trade-offs. Viewing an email you’d like to file on your iPhone or iPad, tap the Folder icon in the toolbar at the bottom. This will bring up the menu showing a list of all the folders on that particular account. Tapping any one of those folders will move your message to the destination folder. If you would like to move the email to a different account, tap Accounts in the top-left corner of the screen (or swipe from the left side of the screen), and that will bring you to a list of all of your email accounts. From there you can select a different email account and get that email account’s list of folders. Tap the appropriate folder in the other email account, and iOS Mail will send your email there. If at any point you decide you don’t want to file that email after all, tap the Cancel button, 122
and you’ll go back to your email.
select a few (or all) of your emails. As you tap each circle, it fills in blue with a white check mark. You can also select all messages with the Mark All button. Tapping the Mark All button also gives you options to flag or mark messages as unread. Once you’re done selecting messages, iOS Mail gives you options to trash the selected emails or move them to a different folder using the same mechanism for moving a single message.
Screencast 4.9 Moving Email Messages in Apple Mail on the iPad and iPhone
If you’re already a keyboard junkie on the Mac, tapping and filing each individual email will start to make you crazy. Fortunately, iOS Mail has a solution for processing multiple emails at the same time. To do so, while viewing your email list, press the Edit button on the top-right corner. iOS Mail then moves all of your emails slightly to the right on the screen and inserts empty circles next to each message. Tap on the circles to 123
Another recent improvement in Apple Mail is the ability to process email without opening it. If you swipe slowly from right to left across an email in your message list, iOS presents Delete and Flag buttons. There is also a More button. Tapping that opens additional options for processing email such as Reply to All, Forward, Flag, Mark as Read, Move to Junk, and Move Message... buttons. This gesture has become second nature for me and I use it to blast through my inbox on my iPhone daily. In iOS 8, Apple added an additional gesture for left to right where you can mark a message as read or send it to the archive. This preference is set in the Mail Preferences screen in Mail→Swipe Options.
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Another common problem with Apple Mail on the iPad and iPhone before iOS 7 was accidentally filing emails in the trash or wrong folder. When that happened, you had to navigate to the misfiled folder (or trash), find the lost email, and then manually move it to its proper location. That was really time consuming. Now if you misfile a message, shake your iPhone or iPad like you are auditioning for a salsa band. The iPhone or iPad will then prompt you to undo your last move. (In case you didn’t know it, shake to undo is a common but little known gesture in many iOS applications.)
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Searching Apple Mail the screen (or press Option+Command+F) and start typing your search. For me, this usually starts with typing a person’s name. As you start typing a name, Apple Mail will compare it with with its own knowledge of your email database. As you continue typing, it will suggest names from your known contacts and email correspondents. If you move the mouse point over that name or press
So you’ve mastered reading and filing email messages. How about finding them? Apple Mail also has some great tools for this purpose. SEARCHING EMAIL ON THE MAC Search in Apple Mail has come a long way in the past few years. In order to search your email database, click in the Search bar in the upper-right corner of 126
the Arrow Down key to select that name and press Enter, Apple Mail then focuses its search on that person. You can then click on the front of that person’s name and select To, From, or Entire Message. If you select “To”, you’ll only see emails you sent to that person. “From” displays emails from that person. “Entire Message” displays any emails that have that person’s name (even if they weren’t written by or to that person). That search is contained in a small rounded rectangle in the Search bar. That is called a search token.
emails to that person in February 2013. You don’t have to stop there. Maybe you want to look for emails to that certain person during February 2013 containing the word ornery. To the right of your date token, type ornery and select Any. You can also narrow a search to a specific mailbox by clicking on it in the sidebar or the toolbar, assuming you’ve put some of your mailboxes in the toolbar. There are more search tokens than name and date.
The great thing about email search tokens is you can use more than one of them. Say, for instance, you wanted to look for emails to a certain person but just emails for the month of February 2013. Type in February 2013 to the right of the existing name token, and then Apple Mail will look for 127
Here’s a rundown of search tokens:
list of emails with those types of attachments.
Name
All Text
Search for a name including messages sent to or from that person, or in the entire message.
If you don’t select a specific token, Apple Mail will search the entire message.
Date
Using the above criteria, I’m usually able to find anything I’m looking for. There is more you can do, though. The Search bar follows Boolean logic (AND, OR, NOT). Boolean terms must be in all caps to work. You could, for instance, search for an email message that contains pork chops AND applesauce. The Boolean term NOT will exclude any email with that term in it. The minus sign (-) in front of a word works the same as NOT. For example, pork chops AND applesauce -peter looks for an email containing the words pork chops and applesauce but not the word peter.
Search for a specific month (February 2013), year (2013), and even date range (2/1/13-3/15/13). Subject Look for particular words in the email’s subject line. Attachments Type PDF, Keynote, iWork, Doc, Excel, or any other file format you like in the Search bar and Apple Mail will give you a 128
Remember these email searching tricks because they are going to help you make some great Smart Mailboxes, covered later in this chapter.
you see now why I’m against making big heaping piles of email folders? It isn’t that hard to search out email anymore. Screencast 4.10 demonstrates using search tools in Apple Mail.
As you can see, with a little effort you can drill down pretty deep, pretty quickly. Can
Screencast 4.10 Using Search Tools in Apple Mail on the Mac
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SEARCH EMAIL ON THE IPAD AND IPHONE Searching email on the iPhone and iPad is done through the Mail Search bar. To get there, go inside any mailbox on your iPad or iPhone and pull it down. This exposes the Search bar. Type in your search term, and your iPhone or iPad will search for you. There are buttons to conduct the search in the current mailbox or in all of your mailboxes. There are no search tokens on iOS devices like those found in Apple Mail on the Mac. The iPhone or iPad will report back immediately with any matching emails currently downloaded and then start searching your email server for any additional email messages. This illustrates one of the issues with email on the iPad and iPhone. On your Mac, all of your emails exist on your hard drive; that isn’t the case on the iPhone and iPad. These portable devices have limited storage capacity, and some people (like me) have a lot of email. Apple, wisely, doesn’t want someone with a 12GB email database to be left with only 4GB on a 16GB iPhone, so the iPhone and iPad don’t download all of 130
Searching Apple Mail on the iPhone
your email. Instead they download only the most recent emails and access the rest through the email database. That involves going to the Internet and slows you down a bit. iOS Apple Mail also isn’t as powerful as
the Mac version without those great search tokens. On the brighter side, with iOS 7, searching mail on iOS devices got a lot faster. Screencast 4.11 demonstrates using search tools in Apple Mail on the iPad.
Screencast 4.11 Using Search Tools in Apple Mail on the iPad
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EMAIL FLAGS
with an alarm klaxon going off. Fortunately, that is pretty rare, but it is nice having that tool available when necessary.
Flagging an email now may help you find that email later in Apple Mail. A flag is simply a marker that tells Apple Mail “I am special”. Apple Mail has built-in filters that will display only flagged messages. In Apple Mail on the Mac, there are several different colored flags to choose from. Unfortunately, the colored flags all show up in iOS Apple Mail as orange.
Screencast 4.12 demonstrates setting and using flags in Apple Mail.
Screencast 4.12 Setting and Using Flags in Apple Mail
I rarely use flags. Because I’m pretty regimented in the way I handle email, I find I simply don’t need flags that often. Occasionally, however, I will get swamped. My email will start to accumulate, and I simply won’t have time to process it properly. If I’m buried like that and see an email that is very important but something I can’t deal with immediately, I will flag it for later. To me, a flagged email truly is an email 132
SECTION 6
Writing Email with Apple Mail You wouldn’t think there is any reason to include a section on how to write an email. We’ve all been writing email for years. In chapter 2, I explained a better order for writing email messages. There are, however, a few tricks you should be aware of when writing email in Apple Mail.
http://www.google.com/url?sa=t&rct=j&q= %20paperless&source=web&cd=2&cad=rja&ved= 0CEcQFjAB&url=https%3A%2F %2Fitunes.apple.com%2Fus%2Fbook %2Fpaperless%2Fid520393162%3Fmt %3D11&ei=7YT6UayMLKWEiwKfuYGACw&usg=AFQjC NEhQPcZNamr58mqY4hlDQELR_2NDw&sig2=sigjrn rpdHiPa3J2uCkrzA&bvm=bv.50165853,d.cGE
Not only is it inscrutable, it also takes a lot of characters so it may end up on more than one line in your email client. Sometimes email clients on the other end will look at that line break and not realize it is a hyperlink, so the recipient not only gets an ugly link in the email, they also get a broken
THE EMBEDDED HYPERLINK Quite often you’re going to want to link something in an email. The trouble is a lot of links on the Internet are pretty ugly. Here’s an example of a link for my Paperless book in the iBooks Store: 133
Screencast 4.13 Creating Embedded Hyperlinks in Apple Mail on the Mac
one. In Apple Mail, you can fix this with embedded hyperlinks. With an embedded hyperlink, you can type a small bit of text and then bury in that text a hyperlink to somewhere else. The magic key combination for doing this on the Mac is Command+K. Highlight the text you want to link, hold
down the Command+K keys simultaneously, and Apple Mail opens a window for you to paste in your link. When you’re done, the text will display with a different color and your recipient will know to click on the link to go off into the Internet. You can also create an embedded 134
QUOTING LIMITED TEXT IN A REPLY
link through the Apple Mail menu at Edit→Add Link... path. There is one downside to embedded links. If your recipient forwards the message, the next recipient can’t use it. They don’t work in forwarded messages.
Another nice touch in Apple Mail is the ability to quote a limited portion of an email in your reply. Let’s say you receive a 2,000word email, in the middle of which is buried a single question. If you highlight the question and press Reply, the draft reply will only include the selected question as quoted text. This makes for a much cleaner response. This trick works on the Mac, iPad, and iPhone versions of Apple Mail, and I use it every day.
Embedded hyperlinks on iOS aren’t as easy. There is no current mechanism in iOS Apple Mail to embed a hyperlink. There is, however, a way around this. There are several third-party text editors that support creating hyperlinks, and some of those will export directly to a new mail message. I demonstrate this using Drafts in chapter 6, where I include screenshots showing how to create an embedded hypertext link.
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Moreover, using selected text for a reply is a great way to kick off an inline reply, explained in chapter 2. SETTING AN EMAIL’S SEND-FROM ADDRESS
on the one you want to use and continue composing your message.
Because most of us have multiple email accounts, we are going to occasionally need to set the account we want the email to be sent from. It doesn’t make sense to send an email to a client from your personal address, and it doesn’t make sense to send an email to your friend from your work address.
This works fine for most people but for those of us who are impatient and don’t want to lift our hands off the keyboard to change the email send-from account every time we want to send a message, you can create a keyboard shortcut on the Mac. In order to do this, go into the System Preferences pane on the Mac and create a keyboard shortcut. You can create one for each of your email accounts and then tie them to a keyboard combination. I do this for all of my email accounts and find it much
On the Mac, in the compose email dialog box, there is a selection box above the message body window where, with your mouse, you can click on the email address you want the message to be sent from. Click
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quicker for changing the send-from address before firing off my emails. Screencast 4.14 demonstrates how to do this. Changing the send-from account on an iPhone or iPad requires tapping the Cc/Bcc, From: field at the top of the message. This unfolds to show each of those fields. You can then tap the From: field and select the email address from which you want to send the message. This is also how you add carbon copy (Cc) and blind carbon copy (Bcc) recipients. One of the improvements to iOS Apple Mail with iOS 7 is a sort of logic where Apple Mail predicts which email account you want to send from. If you are sending an email to a coworker, for instance, the app is likely to set your work account as the send-from account. It is right more often then not, but you still should keep an eye on what account you are sending from.
Screencast 4.14 Setting Keyboard Shortcuts for the Email Send-From Accounts in Apple Mail
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ADDING ATTACHMENTS
screen with your mouse until Spaces moves over to the Mail screen. If you find this as vexing as I do, get a copy of Unclutter (Mac App Store) (website), Yoink (Mac App Store) (website), or one of the myriad other apps available in the Mac App store designed to solve this very problem.
You can add an attachment to an email message on your Mac by clicking the Paper Clip icon button and selecting the attachment from your Mac. You can also drag a file into the body of your message, and Apple Mail will add it as an attachment. I’ve become so reliant on dragging attachments into messages that when I use an email client that doesn’t support this, I find it jarring. When working with Apple Mail in full screen mode, dragging attachments into messages gets trickier. You need to pull the file to the edge of your
Another nice touch in Apple Mail is the ability to set the size of a photo attachment for your email. With rapidly-increasing files size of photos taken by modern digital cameras, it can make a lot of sense to reduce the file size of photo attachments.
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application. From there, tap the Sharing button to share the subject PDF file via email. That creates a new email message and attaches the file. This isn’t particularly intuitive but it works. This is one thing I'd like to see get easier with future versions of iOS Apple Mail. Screencast 4.15 demonstrates how to use email attachments in iOS.
On iOS, adding attachments is not as intuitive. Tap and hold inside an email message, and Apple Mail provides a pop-up with the option to insert a photo or video file. It does not, however, give you the ability to insert a PDF or other type of file. In order to do that, you need to open an application on your iPhone or iPad that manages the source file. For instance, for a PDF file, open your favorite PDF
Screencast 4.15 Making Email Attachments in iOS
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With OS X Yosemite, Apple added the ability to send large attachments from iCloud accounts using Mail Drop. Normally you cannot attach large files to emails. Most email servers choke on anything larger than 10MB which, in this day and age, isn’t very large. With the addition of iCloud Drive, Apple Mail now has the ability to automatically upload oversized attachments to iCloud Drive and serve that to a recipient via a link. This is an improvement over existing solutions that require you to separately upload and create a link for embed. If your recipient is also an iCloud subscriber, their Apple Mail will automatically download the attachment making the process even easier for users.
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MINIMIZING EMAIL DRAFTS ON IPHONE AND IPAD One problem that always drove me nuts on iOS is the way I'm locked down as soon as I start composing an email. Traditionally, you couldn’t, for instance, go refer to a different email message while composing a new one short of saving the message as a draft and completely backing out of the composition screen.
Screencast 4.16 Minimizing Message Drafts in iOS
With iOS 8, you can now swipe a draft message’s title bar down and it will park itself at the bottom of the screen. You can then look through other messages and then go back to your compose window by tapping in the title bar at the bottom of the screen This even works for multiple messages.
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Shift+Option+Command+V
pastes text and matches the current style. This is useful when pasting text copied from your browser.
USEFUL MAC KEYBOARD SHORTCUTS There are several more useful keyboard shortcuts when writing a message in Apple Mail on the Mac:
Shift+Command+T
sets the current message to plain text mode and removes all formatting.
Command+S
saves the current message.
Command+K
inserts a hyperlink for the selected text to a website or download link. Screencast 4.13 demonstrates this.
Shift+Command+D
sends the current message. Shift+Command+: (Colon)
toggles spelling and grammar.
Control+Option+Command+P
saves the currently selected email to PDF.
Shift+Command+V
pastes text as a quotation. 142
In addition to these, you can also create a keyboard command for any menu item in Apple Mail using your Mac’s keyboard shortcut feature, as demonstrated in screencast 4.14. As a bit of advice about keyboard shortcuts, don’t try and learn all of these shortcuts in one go. Pick a few that you can use often and get comfortable with those. Once they are second nature, pick a few more. Before long, you’ll be flying through Apple Mail without lifting your hands from the keyboard.
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EMAIL SIGNATURES Automating signatures in your email is one of the easiest ways to save yourself a lot of time. Every email you send is going to include a signature. Why not have the computers do this for you? I explained at length the good, the bad, and the ugly of email signatures in chapter 2. So how do you go about setting up an email signature in Apple’s Mail app? accounts and even have multiple signatures per account. If you do that, when writing an email message, Mail will give you the option to select which signature to use with your outgoing mail. You can also check the box to have Apple Mail match the typography of the mail message with the inserted signature.
EMAIL SIGNATURES ON THE MAC Go to Mail→Preferences... (or press Command+, [Comma], which opens Preferences in most Mac applications). Then select the Signatures tab. From here you can start adding stock email signatures. Tap the Plus (+) icon button and go to town. You can attach signatures to specific email 144
Using Apple Mail’s built-in signatures makes a lot of sense if you have just one signature you always use. I have several different stock email signatures:
XOXO, David
Your pal, David
With kind regards, David
Cordially, David
hands are already on the keyboard, they are much faster. Screencast 4.17 demonstrates how to set up email signatures and use TextExpander on the Mac.
Screencast 4.17 Setting Email Signatures on the Mac
I don’t particularly like you, but I’m sending this anyway, David Rather than setting these up in Apple Mail, which requires a lot of keystrokes and mouse movements with each message, I use TextExpander (website) snippets. For instance, typing yp, triggers Your pal, David. Because the TextExpander signatures are triggered by key combinations and my 145
EMAIL SIGNATURES ON IOS Mail signatures are managed on iOS in the Mail, Contacts, Calendars tab of the Settings application. In this window, you can set a single signature for all accounts or specify a separate signature for each mail account. Since Apple doesn’t support TextExpander touch (iOS App Store) (website) in Apple Mail for iOS, I use this feature on my iOS devices for all of my email accounts. For my day job, I have a signature that includes my name, my company name, and my phone number. For my personal and MacSparky accounts, the autosignature just signs David. I can then dictate in the closing or use iOS’s keyboard shortcut feature. Screencast 4.18 demonstrates email signatures in Apple Mail on the iPad.
Screencast 4.18 Setting Email Signatures on the iPad
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APPLE MAIL STATIONERY
Apple Mail Stationery on the Mac
Several years ago, Apple added stationery to Apple Mail. When composing a new message in Apple Mail on the Mac, you’ll see a Stationery icon button on the far right in the toolbar. (It looks, not surprisingly, like a very small piece stationery.) Clicking on that opens up a series of formatted stationery forms to choose from. They have multiple themes including birthdays, announcements, photos, sentiments, and plain old stationery. You can select any of the professionally designed stationery, replace the stock text and images with your own, and then send it off. It makes for a very attractive email. It works pretty well, and it even displays properly in webmail clients. I often use it to send birthday greetings to friends. This is another feature that’s only available in
Apple Mail. There are some third parties that sell additional stationery forms for Apple Mail. Equinux (website) has one of the biggest selections of additional stationery. 147
USING HANDOFF With iOS 8 and Yosemite, Apple added a new feature called “Handoff” that let’s you start work on one device and continue it on another. Let’s say, for instance, you are working on a long email response when you suddenly get called away from your Mac. Using Handoff, you could open your iPhone or iPad and a Mail icon shows up in the lower-right portion of the lock screen. Swipe that up and your Mac hands off the draft email to your iOS device and you can pick up where you left off. I originally thought this was a gimmick but now I find myself using it all the time with Apple Mail.
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SECTION 7
Apple Mail VIPs One of the challenges of email— perhaps the challenge—is separating the wheat from the chaff. We have these email addresses, which are often public, and anyone (or any robot) in the world can send something to us asking for our attention. Some of those messages are from kind, emotionally mature humans. Many are not.
applications will treat them with special love and care. There is a separate email folder that holds VIP email. This way, if you only have a few minutes, you can check just the VIP box and make sure there is nothing important from people you consider important.
VIP
You can also customize notifications settings on the Mac and iOS so that you only get notifications from VIPs. This is an excellent way to minimize distractions and still get the notifications you need. If you turn off all notifications except for your spouse, your
To help solve this problem, Apple added VIPs to Apple Mail. You can mark someone such as your spouse or crazy boss as a VIP, and the Apple Mail Mac and iOS 149
crazy boss, and your favorite clients, then an email notification means something to you. It is more than an unwanted distraction.
Intelligently using VIPs, you can go back and turn on those notifications I kept telling you turn off earlier. Just make sure the notifications are for VIPs only.
I think VIPs were a great addition to Apple Mail and use them often. It is one of those features that make it hard for me to consider leaving Apple Mail as my primary email client. In addition to having my family and coworkers set as VIPs, there are some clients and friends who have made the cut. I frequently put people on the list temporarily. If I’m in the middle of a contract negotiation, I’ll make the other lawyer a VIP and then remove her from the list after we are done. If I’m about to record a Mac Power Users episode with a guest, I make that guest a VIP so I’ll know immediately if she emails me. If you are using Apple Mail, you should start using VIPs both early and often.
SETTING VIPS ON THE MAC The easiest way to make someone a VIP in your Mac is to hover the mouse cursor to the left of their name on your email list or in an email message. The outline of a star appears. Click on it and the outline of the star darkens. Congratulations, you just made that person a VIP. You can also do this by tapping the Arrow to the right of 150
their name and selecting Add to VIPs. To remove the person from your VIP list, do the same. It is so easy to add and remove people from VIPs that there is no reason not to use it aggressively. Don’t put yourself in a rut of picking a few people and forgetting about it. Instead, make your VIP list dynamic, and look constantly at your email recipients for potential temporary VIP users. Once you add someone as a VIP on your Mac, any email from that person (from any of their accounts) will get the VIP treatment. Because you are letting VIP contacts through your email firewall, this allows you to have your cake and eat it too. Specifically, you can get rid of most email notifications while only keeping those that you really need.
Apple Mail ships with a useful VIP Smart Mailbox that allows you to easily see all VIP email. Screencast 4.19 Using Apple Mail’s VIPs for Fun and Profit
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SETTING VIPS ON IOS You can set someone as a VIP on either your Mac or iOS device and iCloud will keep track for you. On your iPad or iPhone, tap on the person’s name in the Address bar, and a pop-up menu appears that includes the option to add the person to your VIP list by clicking Add to VIP. It works the same for removing people from your VIP list. Screencast 4.19 demonstrates creating VIP users and some of the advantages of having an active VIP list.
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IMPORTANT MAIL THREADS Starting with iOS 8, Apple Mail lets you designate specific email threads as very important in addition to emails from people you designate as VIP. To set a thread as important, tap the flag button at the bottom-left of the screen while viewing an email in the thread. Then tap Notify Me. Apple Mail puts a little alarm bell icon on messages in the thread and when a new one arrives, you get notified. If you are trying to close a deal or expecting to meet someone, this is an excellent way to get messages without having to make every person in the thread a VIP.
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Smart Mailboxes So far, I’ve spent plenty of time preaching against having too many mailboxes in your mail setup, but what if there was a special sort of mailbox that didn’t require you to move messages into it but instead simply made its own lists of messages that it thought you should read? What if you could use several of these special mailboxes and even have a single email show up in them multiple
times? That’s right. I’m talking about a mailbox that defies the laws of mailbox physics. I’m talking about Smart Mailboxes on the Mac version of Apple Mail. Smart Mailboxes are not a destination for mail like an Archive or Action folder would be, but instead a sort of filter that scours your email messages collecting just those that you want. Easy to use, Smart 154
Mailboxes look through all of your various mail files and displays only those emails with an unread status. If you are using some of the advanced techniques taught in this book, you are going to have unread mail all over your system. If you really want to see what’s new, this simple Smart Mailbox solves the problem. Gallery 4.5 includes the setup screen for a Smart Mailbox displaying all unread messages. You can go a lot deeper though.
Smart Mailbox Search Criteria
To set up a Smart Mailbox, click the Plus icon button in the lower-left corner of Apple Mail 155
on your Mac. That lets you select from creating a new conventional mailbox (that resides on your POP or IMAP server) or a Smart Mailbox. Click Smart Mailbox. Alternatively, select Mailbox→New Smart Mailbox... from the Mail Menu bar. Apple Mail creates a new Smart Mailbox. You can give your new Smart Mailbox a clever name and start setting up its filter criteria. Conditions may include the sender, recipient, and other recipients. Using this, for example, you could make a Smart Mailbox that only has messages from your partner. Apple Mail will also look at the date viewed,
last read, and what account it came in on. You can filter a Smart Mailbox on a message’s priority and flag status (or lack thereof). The list goes on with filters based on whether or not the message was replied
to, what mailbox it is in, and its attachments. Using these criteria creatively, you could develop some pretty useful filters. For instance, if you are working on a project, you could create a group of the
Screencast 4.20 Creating Apple Mail Smart Mailboxes
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Gallery 4.5 Sample Smart Mailboxes
This shows all non-junk email that is still unread.
people in your address book who are essential to that project. You could then make a Smart Mailbox that looks for all emails in the last three months with just people from that group. It doesn’t matter where those emails actually reside on your email server. They could be in your inbox,
Archive folder, Action folder, or any mail folder you create. They will all show up in the Smart Mailbox. Smart Mailboxes organize the mail for you once you establish their criteria, and they are always comparing your entire email 157
library to their rules, even the mail they’ve already listed. For instance, if you set up an Unread Smart Mailbox, the act of reading a message will result in the message being marked read, and after you are done reading it and move on to the next unread message, it gets booted from your Unread Smart Mailbox. This doesn’t mean the message moves out of your inbox, gets archived, or anything else. The message simply disappears from the Smart Mailbox because it no longer qualifies for the club.
demonstrates how to create and use Smart Mailboxes and gallery 4.5 shows some of my favorite Smart Mailbox recipes.
Smart Mailboxes are a great way to manage unique or project-related mail messages. Unfortunately, it only exists on the Mac. Smart Mailboxes don’t appear on iOS devices. Apple Mail for iOS does include a predefined set of quasi-smart folders, but these aren’t nearly as powerful as folders you can create yourself. Screencast 4.20 158
SECTION 9
Apple Mail Markup and Extensions With the release of OS X 10.10 Yosemite added a clever feature to Apple Mail that lets you annotate attachments right in the mail message. The feature is called Markup and it can make sending an image with a little doodle, or arrow, or other annotation loads easier.
job of figuring out what you are doing and cleans it up. Markup is one of Apple’s first official implementations of OS X extensions, which arrived with Yosemite on the Mac and iOS 8. As swell as Markup is, I'm even more excited about what other extension services Apple (and others) can bring to the Mac and iOS. Screencast 4.21 demonstrates Apple Mail Markup.
To kick it off, click on a file inside a mail message. An icon appears in the upper-left corner. Click it and select Markup and you’re off to the races. You can draw lines, shapes, and text. Even if you’re drawing skills are a little rough, Markup does a good
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Screencast 4.21 Apple Mail Markup
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S E C T I O N 10
Apple Mail Rules APPLE MAIL RULES
shows an inexhaustible ability to annoy you? Rules can fix that.
I don’t know about you, but I’ve always wished that I had my own personal robot. When I was a kid, I wanted a robot to clean my room and do my homework. These days, I’m looking for a robot just to deal with the amount of information being thrown at me everyday. The mail rules feature in Apple Mail is about as close as you’re going to get to having a robot to deal with email for you. This is perhaps the most underutilized feature in Apple Mail. Have you received email repeatedly from someone that doesn’t quite qualify as spam but at the same time
Rules apply a series of filters to all of your incoming mail. You can set very specific filters that, in turn, can apply very specific actions to emails matching your criteria. Rules are the natural successor to Smart Mailboxes. Where Smart Mailboxes find and display messages, mail rules find email messages and do things to them. For instance, at the most basic level, you could have a rule that any email coming from the domain IAmAnnoying.com gets immediately marked as read and sent to the trash can. I 161
Criteria for Apple Mail Rules
have a remarkable number of rules that are this simple. Every time I get a marketing email, I create such a rule, muttering softly under my breath, “IAmAnnoying.com, you are dead to me.” The good news is it truly is dead to me. Anytime an email arrives from that domain, Apple Mail marks it as read and deletes it before I ever see it, and I never see another email from IAmAnnoying.com. You can also use rules to forward messages. For instance, if you wanted to make sure a coworker gets every email from a key client, you could set up a rule for that. It would simply look for any email coming from a particular address. Whenever it detects the arrival of a message from the client, the rule springs into action. You could even color the email red, then forward a copy to your coworker’s email address. I demonstrate a rule similar to this in screencast 4.22. I think a lot of people are intimidated by Mail’s rules because most of us are not computer programmers and something this powerful sounds like high-order wizardry. That’s not true. Anybody reading this book can set up a very sophisticated set 162
of useful rules.
Apple Mail Rule Actions
So how does it work? Mail’s rules are modular. First, pick the criteria of a mail rule that qualifies the message for the rule. There are a lot of options including the sender, the recipient, other recipients, the subject line, whether or not the message is addressed to your full name, the date sent, the date received, which of your email accounts it was sent to, whether or not the sender is in your contacts, a previous recipient, a VIP, or a member of a group from your address book. That is not all. You can also make a rule based on the content of the email. If, for instance, the email includes the
word cockamamie, you could apply a rule to it. There are also filters looking for emails marked as junk, signed, encrypted, or with high, normal, or low priorities. Apple Mail will even look at attachment types and names when applying rules. As you can see, this is a powerful set of filters. You can combine them to have filters require all or any of these criterion to be satisfied.
Once Apple Mail finds an email matching your criteria, there is an equally large list of things you can do with it, including copying and moving the message, setting the color, or playing a sound. For instance, when my 163
daughter was out of town once, I had a rule that would play a chime any time I received an email from her. (This was before Apple added VIPs and notifications to Apple Mail on the Mac.) You can also make the Mail icon in your dock bounce or send yourself a notification. That notification feature is a
new one and integrates very nicely in OS X Mavericks. You can also create an autoreply, forward, or redirect of the message. If it is not worth your time, you can mark it as read or even delete it. If it is special, you can flag it. Finally, you can run an AppleScript for when the mail arrives
Screencast 4.22 Creating and Using Apple Mail Rules
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that could conceivably do just about anything on your Mac.
My Friend-Spammer Rule
messages while still receiving the important ones.
Here is how I solved it with my spammy friends. I noticed that all of the spammy emails were copied to a whole group of people, including people I didn’t know. So I made a mail rule that looked for any email from my spammy friend that was also copied to one of these other strangers. Whenever Apple Mail saw an email matching that criteria, it marked the email as read and trashed it. Since any important emails this person sent me would not be copied to the stranger, those emails never got caught by the rule. This simple,
Let me give you another example. Do you have a friend-spammer? That is a friend that occasionally sends you an important email but much more often spams you with snopes-worthy (website) urban myths, pictures of kittens dressed like sailors, and—of course—chain emails. As a first line of defense, buy them a copy of this book and tell them to stop the madness. If they resist, however, you’ve still got to figure out how to stop seeing their spammy
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Gallery 4.6 Sample Apple Mail Rules
This rule takes those nice “someone liked you on Vimeo” messages and marks them as read and sends them to the archive. I like having them but don’t need to read every one. little rule saved me a great deal of time and aggravation.
and emails from your sales leads green. Then when you look at your email box, you’ll be able to quickly find the emails you need most.
Another good use of email rules is to color your email. Make emails from your boss red 166
Setting up new rules is done in the Rules tab of the Mail Preferences. This screen shows a list of existing rules but also has a button to create entirely new ones or even duplicate an existing rule, which can be useful. This is also the window where you activate (or deactivate) existing rules with checkboxes. Screencast 4.22 shows how to set up rules of your own. Gallery 4.6 shows the window along with some of my favorite rules.
Mac trashes an incoming email from IAmAnnoying.com, that email will go to the trash on your iPhone at the same time. Sometimes I’ll see an email briefly appear in my inbox on my iPad and then suddenly disappear. That always makes me smile because I know my mail rules are doing their job. I know some people who keep a Mac running in their homes 24/7 partly for this purpose.
Apple Mail on iOS doesn’t have rules like the Mac does. If you’ve got a Mac at home or in the office and use rules, leave Apple Mail running on your Mac. Let it do the heavy lifting for your email management. Because you are using IMAP email accounts (You are using IMAP, right?), the effects of all of your rules will show up automatically on your iOS devices. If, for instance, your 167
SERVER-SIDE MAIL RULES WITH ICLOUD
the rule sets available in Apple Mail, users could set up their rule sets in the cloud and not have to run a separate Mac somewhere to manage email for them. As iCloud continues to grow, this is one of my biggest feature requests: better server-side rules. Screencast 4.23 demonstrates setting up iCloud Mail rules.
If you are using iCloud, Apple has some server-side rules that operate at Apple’s servers. However, these rules aren’t nearly as robust as those found in Apple Mail on your Mac (or Gmail’s server-side rules covered later in chapter 5). To activate them, log into your iCloud account at iCloud.com, click the Mail icon button, and tap Rules. The cloud-based rules let you pick just one field for the filter (you can’t combine them like you can on the Mac). The filter set is also more limited, dealing with the sender, recipient, other recipients, and the subject line. Once an email falls in the criteria, the Apple iCloud servers will delete, move, or forward the email. If Apple could improve the iCloud server-side mail rules to something like (or even closer to)
Screencast 4.23 Setting Up and Using iCloud Server Mail Rules
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S E C T I O N 11
Additional Useful Apple Mail Settings Mail→Preferences.... You can also do so with a keyboard shortcut using Command+, (Comma). The Preferences screen has a series of tabs across the top: General, Accounts, Junk Mail, Fonts & Colors, Viewing, Composing, Signatures, and Rules. Several of these items have already been covered in this book, but the others are worth a mention.
There are some additional settings of note in both the Mac and iOS versions of Apple Mail. ADDITIONAL SETTINGS ON THE MAC Access the Preferences panel in Apple Mail in the Menu bar by clicking
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THE GENERAL TAB
you can give Apple Mail instructions as to whether or not it should search the trash, junk mail, and encrypted messages when doing a search.
In addition to setting notifications in the General tab, you can also change the OS X for Mac default mail reader. I’m going to cover some alternative mail applications later in this book, and if one tickles your fancy, you set this up here in Apple Mail. Sometimes you’ll receive calendar invitations embedded in an email message. There is a setting to automatically add the events to your calendar. (I prefer to do this manually.) OS X for Mac has a Downloads folder in every user’s account. This is where Apple Mail sends downloaded files by default. If you want them to go elsewhere, you can change it from this screen. You can also set the behavior for what to do with those downloads. For instance, you could have Apple Mail automatically delete them after you delete the related emails. Finally, 170
THE ACCOUNTS TAB I’ve already covered setting up new email accounts. This tab has even more settings related to your email accounts including the ability to turn your account on or off and how the application manages drafts, sent emails, junk mail, and trash. If you want to get very specific control over your email accounts, this is the place.
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THE JUNK MAIL TAB Apple Mail has its own built-in support for detecting junk mail. I’m going to cover spam emails in further detail later in chapter 7. The Apple Mail junk mail filter and support isn’t bad, but there are better options explained later.
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THE FONTS & COLORS TAB If you’re not happy with Apple Mail’s default text display, go here to change fonts and point sizes. You can also change the colors Apple Mail uses for displaying quoted text in this screen.
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THE VIEWING TAB There are several options relating to how Apple Mail displays messages, including whether or not it displays images and how it groups related messages together. This screen also presents several options to customize how Apple Mail displays images.
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THE COMPOSING TAB This screen has a list of useful options for composing email. It lets you set the default email message as rich text or plain text. Settings for spell checking and addressing new email messages are found here as well. This screen also includes preferences for email responses, such as whether or not to include a quote of the text from the original email message. Apple Mail’s signatures and rules tabs are already covered elsewhere in this book.
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ADDITIONAL SETTINGS ON THE IPHONE AND IPAD
by default. You can also change the flag shape between a dot and a flag. If you’re concerned about accidentally deleting an email, there’s a switch you can turn on that will request Additional Mail Settings on the iPhone permission before deletion. I would recommend this only if you have a low volume of email, otherwise you’re going to spend a lot of time confirming deletes. You can also
On the iPad and iPhone, settings are accessed not in the Mail application but instead the Settings application. Tap on the Mail, Contacts, Calendars button for the mail settings. From here you can make adjustments to your accounts and set your accounts to push new email or have the application fetch email on your schedule (or when you open the Mail app). These topics were covered earlier in this chapter. You can also adjust the number of lines Mail uses to preview your messages. By default Apple Mail previews two lines. I set mine at four lines, which gives me a bit more information and allows me to open less mail. If you frequently use the carbon copy field, there’s a switch to allow you to leave that on 176
instruct Apple Mail to load remote images (or not) and display email messages by thread. Email threads allows you to see both the email messages and the responses directly related to it. I prefer viewing by thread. If you must retain a copy of your email, there’s a way to send a blind copy of all of your outgoing email to yourself. Here is also where you can set up signatures and the default email account used for sending messages. Overall, there are quite a few customization options for Apple Mail on the iPad and iPhone. Spending five minutes to adjust some of these settings will make your email experience better suited for you.
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S E C T I O N 12
Apple Mail Automation Another advantage of using Apple Mail is that it has pretty terrific automation support. There is a small team at Apple that spends its time thinking about automation on your Mac. These are the people that brought us things such as AppleScript, which allows you to use a scripting language to give your Mac commands, and Automator, which reduces automating tasks on your
Mac to dragging and dropping prebuilt tasks on top of one another. Automator is something anybody can pick up with just a little bit of effort. Moreover, Automator includes some really great tools for working in Apple Mail. Microsoft also gets the value of automation and has built several Automator actions for use in Microsoft Outlook for the Mac.
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Let me share an example. Pretend you are a salesperson and you go out on the road and you take notes at client meetings on your MacBook Air. Also imagine you have an assistant that processes those notes for you. In order to make that happen without automation, you need open Apple Mail, address a new message to your assistant, add a subject line, copy the information from your note-taking application and paste it into the new email message, then add your signature and send. When you think about it, that is a lot of steps.
Automator Mail Actions
activate an Automator-created service that does all of the above for you in the background in a way that you don't even see Apple Mail open. I do this with telephone messages at my work. Screencast 4.24 walks you through how I created the script and use it. Looking at the list of available commands for Apple Mail in Automator, there are a lot of options for you to automate your own email workflows. Open Automator and take a good look at these mail automation options. I'm betting that at least one of them will be useful to you.
With Automator you could simply highlight the text in your notetaking app right-click it and then 179
Screencast 4.24 Using Automator with Apple Mail
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S E C T I O N 13
Apple Mail for Mac Plug-ins MAIL ACT-ON
At this point, you are an Apple Mail pro. You understand both the tactical and the technical pieces of making this application sing. Now it’s time to make it dance. A lot of people don’t realize that Apple Mail is extensible. Third-party software developers can write applications that plug into Apple Mail, giving it additional features. Quite a few of them have done so, and there are several additional plug-ins to make Apple Mail work even harder for you.
Note: As this book goes to press, Mail Act-On is not Mavericks compatible. This section was written using the public beta (website) of the Mavericks version that the developer intends to release for purchase by the end of November 2013. Mail Act-On (website) simplifies the process of managing incoming and outgoing 181
email. I explained earlier the ability to automatically file email in different mailboxes using keyboard shortcuts in Apple Mail. That’s a relatively new native feature for Apple Mail. Until Apple added this feature, Mail Act-On was mandatory to streamline mail management. This plug-in still exceeds the native Apple feature in several ways.
developer can bring to an application. It works with all of your mail accounts. It includes the ability to undo rules you have mistakenly applied with Command+Z. It even lets you adjust exactly when the Gallery 4.7 Mail Act-On Screenshots
For instance, Apple Mail’s rules only apply to incoming messages. Mail Act-On expands this to outgoing messages. So if you want to automatically file outgoing messages to a particular folder, this is the best way to pull that off. Mail Act-On’s developer, Indev Software, is —in my opinion—the premier Apple Mail plug-in developer. This plug-in has all the nice subtle touches that an experienced 182
message gets marked as read so it doesn’t screw up any of your other rules. Mail Act-On is one of my favorite Apple Mail plug-ins. Gallery 4.7 includes several Mail Act-On screenshots.
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MAILTAGS
beginning. You can also attach projects, importance, and colors to your messages. It adds data to track due dates for emails and attach them to events and tasks on your Mac. It is, in essence, a bowl of hot steaming metadata poured over your email.
Note: As this book goes to press, MailTags is not Mavericks compatible. This section was written using the public beta (website) of the Mavericks version that the developer intends to release for purchase by the end of November 2013.
This gives you all the advantages of a traditional tagging system. It makes it easier to search and locate specific emails. For instance, if you’ve tagged all emails related to a certain project with a specific project tag, getting access to that entire body of email is as simple as flipping the bit in MailTags for that project tag. You can tag emails as they arrive and as you write them so that all the
For a lot of people, the big selling point of Gmail is the ability to use tags (called labels in Gmail) with their email. (I explain this and Gmail in further detail in chapter 5). However, if you really want tags but also want to stay with a traditional IMAP server and Apple Mail, you need MailTags (website). MailTags allows you to attach keywords and tags to your email messages. That’s just the 184
email related to that specific project will show up.
MailTags, another product from Indev Software, is actively developed and constantly taking advantage of the latest improvements in the Mac operating system. The most recent version added the ability to create notifications based on due dates you assigned to emails using MailTags. Another great feature with MailTags is the ability to apply tags using Apple Mail’s rules. You can automate email tagging and avoid some of the overhead that comes with tagging. One downside is that there is no way to sync the tag information to Apple Mail for the iPad and iPhone, so you won’t see the benefits of your tags there.
The metadata MailTags creates will sync over an IMAP or Microsoft Exchange server so if you have multiple computers, you should get your data on all of them. Gallery 4.8 MailTags Screenshots
A bigger question is whether or not you want to spend time tagging your emails. This depends on you. The search engines in all the modern email clients are very powerful. Using Apple Mail, I can easily 185
search for all email related to a certain person in a certain date range that contain keywords related to a specific project. But all of that is dependent upon the right criteria being contained in those search terms. If someone writes me an email about a specific project but never mentions the name of the project, there’s a chance my search won’t find it. If, on the other hand, I use MailTags and tag every mail related to that project with the project tag, I’m guaranteed to see it. Of course that requires me to take the extra step of tagging each email I write and receive. That time adds up so it becomes a cost-benefit analysis. If investing that time saves you additional time on the back end when you’re looking for these emails, it’s worth it. If, on the other hand, you rarely find yourself searching the tags, then it’s time wasted. You have to decide this one for yourself but if you are
interested in tagging email on the Mac, look no further than MailTags.
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MAILHUB
one sender or in a single thread. You can file or delete all of the messages with one keystroke.
MailHub (website) is another top-tier Apple Mail plug-in. My favorite MailHub feature is predictive filing. When I view a message with MailHub turned on, the plug-in views the message and predicts where I will file it. If the application has it right, pressing Command +Enter files the message in that folder. If MailHub gets it wrong, the application makes it easy for me by pointing to an alternative destination. MailHub also makes suggestions for outgoing emails. If you prefer to file your outgoing emails in project-specific folders instead of a Sent folder, this can be huge. MailHub simplifies dealing with multiple email messages from
Like MailTags, MailHub also has options for email reminders, which show up in your calendar. The reminders include the entire email, which is helpful. MailHub is best for people who use multiple folders for sorting and storing email. If that’s you, you need MailHub. Gallery 4.9 MailHub Screenshots
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CARGOLIFTER
recipient’s mail server is going to reject the mail, and you will, theoretically, get the message returned back to you. If that email included important information, tough luck. This results in much gnashing of teeth every day.
Sending email attachments sometimes feels a little bit like playing a slot machine: you pull the lever knowing you may or may not get the result you want. Specifically, email protocols were never designed to handle large attachments. Different mail servers have different attachment size limits. For some it’s 10MB, for others it may be much more (or much less). The point is when you send an email to someone and you’ve got an attachment that is over that magic number, the
CargoLifter (website) is an Apple Mail plug-in that automatically uploads your email’s attachments to the cloud and adds a link to the end of your email. Putting large attachments in the cloud instead of attempting to attach them to the email makes a lot of sense. This plug-in does the— excuse the pun—heavy lifting for you. The recipient can download the files to wherever she wants on her computer, and you avoid the risk of getting the email bounced or, alternatively, flooding your recipient’s mailbox with unwanted attachments. Another advantage of this workflow is that 188
your PDF doesn’t get stored in someone else’s unsecured email database. CargoLifter supports several different cloud services including Dropbox, Droplr, CloudApp, and YouSendIt. If you’re a lone wolf and you have your own FTP (File Transfer Protocol), SMTP (Simple Mail Transfer Protocol), or WebDAV (Web Distributed Authoring and Versioning) server, CargoLifter can work with those too.Gallery 4.10 includes several CargoLifter screenshots.
Gallery 4.10 CargoLifter Screenshots
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FORGETMENOT
Gallery 4.11 ForgeMeNot Screenshots
So here I am writing a book about email, like I know it all, and during my day job this afternoon, I wrote a detailed email to someone I wanted to impress. I did everything right: I wrote it in the right order. I used some spectacular words. I printed out a hard copy and proofread it with my big, red pen. Then I satisfyingly clicked the Send button only to realize a fraction of a second later that I did not include the attachment.
included. If you want to appear professional when you send an email and you say you’re attaching a file, you probably should attach the file.
Ugh. After I managed to pry my stapler out of the drywall, I sat down, took a breath, and then sent an apologetic email with the attachment
ForgetMeNot (website) is an application that watches your outgoing email for keywords referring to attached files and 190
reminds you if there is not an attachment to the email before sending it. It is already loaded with predefined words, and you can add more custom keywords yourself. It’s a simple little app that solves one of the most common email problems.
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ATTACHMENT TAMER
One of Apple Mail’s features is the ability to automatically resize images before sending. You can send an image in a small, medium, large, or original form. I find this useful, but some people find it annoying. Attachment
Attachment Tamer (website) cures many of Apple Mail’s sins when it comes to the subject of attachments. Sometimes, when sending attachments to our Microsoft Windows brethren, Apple Mail will include an additional file called “ATT0001”. This is a result of differences between the two platforms. Attachment Tamer can send messages compatible with Microsoft Outlook/Exchange and other software, preventing this problem. Also, Apple Mail sometimes truncates the attachment names, making it difficult to discern one from the other. Attachment Tamer displays the full attachment name.
Gallery 4.12 Attachment Tamer Screenshots
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Tamer has a setting to create a default size for automatic image resizing. Attachment Tamer also gives you more control over how attachments appear in your email message. You can specify, for instance, whether PDF files show up as a preview of the document or an icon. This is also true for text and HTML files, images, and audio. Somewhat related, if you want Apple Mail to display attachments as files and not display them inline, you can use a command in the Apple Terminal: defaults write com.apple.mail DisableInlineAttachmentViewing -bool yes
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MORE APPLE MAIL PLUG-INS
MAILRECENT
There are a lot of email plug-ins for Apple Mail available. Here are some more:
MailRecent (website) adds “Copy to Recent” and “Move to Recent” options to the Message menu.
FACE2FACE QUOTEFIX
Apple Mail relies upon your Contacts database to attach photos to your email. Face2Face (website) adds photos from your Facebook and Gravatar accounts to the mix.
If you took my advice about inline replies, you may want to check out QuoteFix (website). It positions the cursor below the original message instead of above it.
FLAGGEDMAILS SIGNATURE PROFILER
This app (Mac App Store) puts access to flagged email messages in your Mac’s Menu bar.
This plug-in (website) gives you even more control over Apple Mail’s Signature feature.
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WINMAIL.DAT VIEWER If you work with winmail.dat files, Winmail.Dat Viewer (Mac App Store) can save you from a lot of headaches.
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S E C T I O N 14
Apple Mail Platform Distinctions Apple Mail is not created equal on the Mac, iPad, and iPhone. Each platform has its own quirks and advantages. The Mac version is best for managing lots of email. This isn’t just because of the Mac’s integrated keyboard. The Mac version has the ability to run all of those plug-ins, AppleScripts, and other automation tools (such as TextExpander) that are not available on Apple Mail for the iPhone and
iPad. Also, because the Mac has a lot more storage than a mobile device, the Mac can hold an entire email archive. Email on mobile devices is more convenient (you can answer email from anywhere) but also more limited. Apple has locked down the iOS operating system in ways that prohibit third-party applications from working with Apple Mail. For example, TextExpander is a great email tool on the Mac but unavailable in iOS Apple Mail. 196
Another challenge with iOS Apple Mail is storage. A lot of us have gigabytes of email. (My Mac currently reports my email library is 14GB.) If you have a 16GB iPhone, you don’t presumably want to use up 90% of your storage with email. iOS Apple Mail stores a limited amount of email on your device and then resorts to the Internetstored version of your email for older mail. Apple has made big strides with Apple Mail such as keyboard shortcuts for filing and organizing, VIPs, and a killer set of tools for creating email rules. Moreover, a lot of these features work across both the Mac and iOS versions, which is extremely convenient. Apple Mail is no longer something you just live with but a powerful, extensible email tool.
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CHAPTER 5
GMAIL
SECTION 1
Gmail In chapter three I explained how surprisingly old the POP and IMAP email protocols are. When Google decided to make its own email product, its engineers took a fresh look at email. Of course Gmail is innovative; it has the backing of perhaps the best company on the planet at managing webbased services and data. Gmail is much more than a front end for an existing email protocol.
Several Gmail features just don’t exist with traditional IMAP mail services, and as email power users, we must take note. Moreover, Gmail is tightly integrated with Google’s suite of utilities, including calendaring, contact management, Google Drive cloud storage, and Google Docs’ productivity tools. If you use Gmail, it makes using these other services even easier. Because Gmail is web based, you can access it through any Internet-connected computer 199
or mobile device. Another advantage of Gmail is Google’s remarkable skill at managing lots of data. Google is full of clever engineers who are constantly cooking up ways to use those Google servers to make email better. Google’s email servers don’t sleep, so all of the Gmail tools I’ll cover in this chapter are working whether or not your computer is turned on.
so much about you that it makes me wonder where this stops being convenient and starts getting creepy. THE CREEPY FACTOR There is a real tired explanation about Google and its products. Google doesn’t charge you for Gmail and other services. Instead, it collects information about your habits and preferences and then uses that information to serve you advertisements that make sense for your preferences. So the way Google makes money is selling ads, not charging you money to use Gmail or other Google services. The point is you’re not paying for Gmail because Gmail is not the Google product—the Google product is you. The more Google knows about you, the better ads it can sell, and the more money it makes.
As this book goes to press, Google is developing its Google Now product. Google Now looks at your email to identify your flight information, view your calendar to determine what time your flight takes off, and sends a notification to your phone letting you know what time you should leave, how traffic looks, and otherwise provide useful assistance. All of this is possible because of the combination of Google services. Indeed, Google can learn 200
As consumers, we need to go into this with open eyes. I don’t think there is a room at Google where people open your email and read your personal correspondence while eating a bacon-wrapped meatloaf sandwich, but I do think there are computers that are constantly scrubbing your Gmail data to look for keywords and terms that tie to products they can advertise to you. Don’t believe me? Look at the sidebar in your Gmail web client. If you write your friend
about how your septic tank recently blew up in a neighborhood apocalypse, there’s a good chance you will see ads for septic tanks on the page. For most people, this isn’t a problem. Indeed, it can be a convenient advantage. Quite often the reason you write about specific products is because you are looking to purchase them. If your email can point you to someone selling the product, all the better. For other people, it’s just too much. I don’t think there is a right or wrong
Google Terms as of November 2013
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answer as to whether or not you use Gmail. I wouldn’t use a free Gmail account for confidential emails. I do use it for my podcast account (and used it for quite a bit more email while writing this book). I’m a little creeped out about how much information Google collects on me. I'm not so creeped out that I think nobody should use Gmail but enough so that I think all users should understand how Gmail works. Moreover, I also think the concept of privacy is in flux, and people increasingly just don’t care that Google scrubs their emails to serve ads.
are talking about so it can serve her better ads. I haven’t agreed to allow Google to do that. Indeed there is litigation against Google on this point as this book goes to press. Gmail is so entrenched at this point that I suspect Gmail is not going to change any time soon. Google has a paid email service for companies called Google Apps for Business. This provides users more privacy, according to Google (website). If you want the benefit of Gmail but are concerned about privacy, consider setting up a Google Apps account to avoid this problem. Either way, there is most certainly an eroding sense of privacy as technology becomes a bigger part of our lives. Companies such as Google and Facebook clearly fall on the side of this argument that the loss of privacy is worth it in exchange for the benefits that arise from
There is another angle to this problem: what about people who are not Gmail users but correspond with Gmail users? When I send an email to my friend through her Gmail account, Google is also presumably reading my message to get a better idea of what we 202
these companies having access to your data. Companies such as Apple and other private IMAP mail servers work on a more traditional model: they aren’t serving you ads but instead taking your money (either through IMAP subscription or as part of hardware sales) to provide you an email service. There isn’t an easy answer to this question, and I'm not going to spend a lot of time navel-gazing about it in this book. Everyone has to make their own decision and should do so with open eyes. If you do decide to use Gmail, there are some pretty great things you can do with it. This chapter will demonstrate my favorite Gmail features and workflows.
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Email in Your Browser Gmail is the ultimate webbased email service. Naturally, it is built around managing email from your web browser. If you’ve spent years working in an email application, this is going to take a little getting used to. Indeed, there are several third-party apps that are designed for Gmail, but if you’re switching to Gmail, I recommend starting in the browser. This is uniquely suited to the
Google experience and, in some ways, better. Even though Gmail is in a web browser, in some ways it feels a lot more like an application: It has keyboard shortcuts. It has special and unique features. It has a settings screen. In other ways, it still very much feels like a website. In my opinion, despite the work of many talented Google engineers, email on the web still does not feel as natural as email in a native application. 204
SECTION 3
Setting Up a Gmail Account getting a username usually takes a few attempts. Once you’ve got your account set up you’ll get to the actual Gmail interface. The left side of your screen lists your mailboxes, labels (explained later), and online social contacts. To find the links to other Google services such as Google+, YouTube, Maps, Drive, Calendar, and more, click the Apps grid to the right of the Search bar at the top of the screen. The rest of the screen is used for some interface buttons and to display your messages.
To create a new Gmail account, go to Gmail.com and click Create an Account, which is located in a blue box in the upperright corner. You will be directed to complete a a series of dialog boxes prompting you for details such as your name, username, password, and other information. It might take a few minutes. Be warned that Google is extraordinarily popular so unless you have a unique name, 205
The Standard Gmail Interface in the Safari Browser
Settings are found by clicking the Gear icon on the right side of the screen, which is where you will manage and enable all the Gmail features covered in this chapter. You can also adjust the density of information provided on the Gmail site with the Comfortable, Cozy, and Compact settings. Traditionally, the Gmail interface was, in my
opinion, hideous. It had bad colors and bad typography, and it looked like something that had 99% engineering and 1% graphic design. It was a running joke that Google made fast, efficient, ugly web experiences. That isn’t true anymore. Google has clearly worked on design a lot, and Gmail is a much more pleasant experience than it used to be. 206
One useful feature for people transitioning to Gmail is the ability to pull email from other email accounts into Gmail for you. If you are moving from a cable company email to Gmail, for instance, this is helpful. To do so go to the Gmail Settings screen and click Settings→Accounts→Check mail from other accounts (using POP3):. Gmail will ask for your account credentials and take care of the rest. You can even send email from within Gmail that appears as if it is coming from your old account, if you like.
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Gmail Inbox Categories In most email applications and services, an inbox is just that: a single place where all new emails collect. Google has a filtering algorithm that it applies to your inbox for you, separating categories of mail. By default these include Primary, Social, and Promotions tabs. If, for instance, an email comes in from LARP-U, your favorite LARP (Wikipedia) costume store, it will go in the Promotions tab and not clutter up your inbox. There are additional categories for updates and forums.
you’ll see 12 Primary messages with tabs including another 30 messages roughly sorted for you. This is similar to the SaneBox service covered in chapter 3. It comes free with a Gmail account and works pretty well. This doesn’t give you the same degree of control as SaneBox, nor does it give you all of the same features, but it is free with every Gmail account and solves the problem of a large, unsorted inbox. Screencast 5.1 demonstrates Gmail Inbox Categories.
The benefit is when you look at your inbox, you won’t see a list of 42 messages. Instead, 208
Screencast 5.1 Gmail Inbox Categories
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SECTION 5
Gmail Keyboard Shortcuts
GMAIL LOVES THE KEYBOARD
that users often forget. In Apple Mail, for instance, you need to hold down three separate keys, Command+Shift+D, to send an email. For me at this point, it’s second nature because I’ve been doing it for so long, but for a lot of people it’s pretty difficult to remember something so intricate for something as simple as sending an email. In Gmail, this takes just two key presses,
Keyboard shortcuts often make the difference between getting your inbox cleared in 20 minutes or five minutes. It is so much faster to keep your hands on the keyboard as you’re working through your email. The trouble with most email applications is that keyboard shortcuts involve complicated combinations of keys 210
Command+Enter, which makes a lot more sense.
in the Gmail Settings tab. Don’t forget to save the settings after turning them on.
That’s not all. Command+N is used to compose a new message in Apple Mail. In Gmail, it is just one key: C. Gmail does keyboard shortcuts better, which is kind of surprising. You’d think that doing keyboard shortcuts in a web browser would be more difficult to implement than in native applications. Whatever the reason, pressing one key instead of two (or three) to trigger a keyboard shortcut is easier to learn, remember, and use. Because these keyboard shortcuts are so easy to trigger, Google makes you turn them on. They don’t want users accidentally deleting, archiving, or moving their emails without realizing what they’re up to. Turn on the keyboard shortcuts in General→Keyboard shortcuts:
Here’s a list of some of my favorite keyboard shortcuts in Gmail. For more, check out Google’s handy list (website). C to compose a new message. R to reply to current email. F to forward current email. J to go to the next email. K to go to the previous email. L to open the label menu. . (Period) to activate the More actions drop-down menu. Y does many things. Its point is to remove a message from wherever you are at. 211
• From Inbox, pressing Y after selecting conversations will archive them.
YO to archive the current email message and move to the next one.
• From Starred, pressing Y after selecting conversations will unstar them.
GC to display your Google contacts. GD to display your draft emails.
• From Trash, pressing Y after selecting conversations will archive them. Screencast 5.2 Gmail Keyboard Shortcuts
• From any label, pressing Y after selecting conversations will remove the label. • It has no effect if you’re in Spam, Sent Mail, or All Mail. GA to display all Gmail you’ve ever sent or received. # to delete current email. GT to display Sent mail. D to compose a new message in a new tab.
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L to open the Labels menu to label a conversation.
CONVERSATION-VIEW SHORTCUTS Google was one of the pioneers in the practice of displaying your messages in relation to one another, sometimes called a threaded conversation. If you look at an email from your friend, for instance, you will see your prior email in the chain displayed right below. Google calls this Conversation View and it’s hugely beneficial. There are keyboard shortcuts that will allow you to navigate while in Conversation View.
Shift+U to mark message as unread. Command+S to save current email as a draft. You really have to see the keyboard shortcuts in action to appreciate how fast they are. That’s why I made screencast 5.2. If, even after all of this, you want further help with Gmail keyboard shortcuts, check out the KeyRocket for Gmail Chrome extension. (website)
N to move your cursor to the newer message. P to move your cursor to the older message. E to archive current email. A to reply all.
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Searching Gmail The reason for Google’s incredible success is its search algorithm. Google was the first company to figure out search and upon that technology, they’ve built their entire company. I remember the first time I used Google search, I thought they must be using alien technologies. Google search was so much better than its competitors at the time that there was simply no contest. They’ve
continued to hold this commanding lead in search technology ever since. The basic search in Gmail is usually all you will need. Gmail does a great job of quickly finding your results as you type in your search. If you need to drill even deeper, you can use modifiers. For example, let’s say you and I have 4,200 emails between us. (We are really close friends.) You want to look for that 214
message from me concerning your pet, a white-faced capuchin monkey named Dreyfus. You could type the following search:
the tools in Gmail (many of which are discussed below) to help refine your search. For instance, you can include operators for whether or not the message is starred (is:starred) or even starred with a specific color (has:red-star). You can limit the query to messages that are marked important (is:important), have an attachment (has:attachment), have been read (is:read), or based upon the message date (after:2012/12/18). You can also modify search terms.
David Sparks subject:Dreyfus You could also replace David Sparks with from:
[email protected]. Google supports several of these operators including Subject:, From:, To:, CC:, and BCC:. Note that the operator is always followed by a colon (:) and immediately followed by the operator subject. (There are no spaces.) Google goes far beyond these basic operators. They take advantage of all
Placing search terms in quotations (”Dreyfus’s diaper”) looks for an 215
exact phrase. Adding the plus sign (+) to the beginning of a word looks for that exact version of the word and not any alternate versions. For instance, +bananas will not return the word banana. Adding the minus sign (-) to a word excludes any emails including that word from the search. For example, subject:Dreyfus -banana will return emails that have the word Dreyfus in the subject line but not the word banana. Google keeps an updated list of its Gmail search terms online (website).
While I’m not a big fan of spending a lot of time organizing your emails into specific message folders, I am a huge fan of power searching your email. If you’ve taken my advice and put most of your emails in a big archive, spend some time getting to know how to search your email application so you can get to what you need faster. Gmail leads the way on this but not as decisively as they used to. Apple Mail also has some very powerful search tools, which were explained earlier in chapter 4.
Once you get good at crafting Gmail searches, you can use the search terms to also create Gmail filters, covered later in this chapter. As boring as this all probably sounds, it is a smart investment of your time to get really good at Gmail search.
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SECTION 7
Gmail Labels Labels are one of placing multiple Gmail’s most copies of the email in compelling features. multiple folders but Gmail labels are, in instead giving it essence, tags. For multiple labels. A instance, an email labeling system could from a customer could let you organize and have labels for see your email in specific products, the multiple ways. As Assigning Gmail Labels customer’s company, another example, let’s product release say you buy a privacy cycles, and other criteria that make sense for scarf (website). You could label the email in it. Unlike IMAP mailboxes, you can apply Gmail with receipt, clothing, taxes, and work multiple labels to a single email. This is not expense labels. You could later search just for 217
emails with the receipt label and your privacy scarf receipt email would be right there. I know a lot of Gmail users have software license labels so every time they buy a new piece of software, they can label the confirming email with the software license and easily find it later. By using Gmail filters, explained later in this chapter, you can automatically assign labels, which gives you the benefit of their organization without the expense of their creation.
email client. They simply don’t know how to process labels and often mistake them for IMAP-type mailboxes. The problem is, however, IMAP email messages don’t go into multiple folders, but Gmail messages can have multiple labels.
Screencast 5.3 Gmail Labels
Gmail labels appear in the left sidebar of your Gmail window. If you create too many and the sidebar starts getting cluttered, you can organize these and even hide certain labels in the Settings window in the Gmail application. Labels are one of the reasons why Gmail often has trouble working in a traditional 218
Some applications resolve this problem by making and filing multiple copies of the email, and others seem to randomly pick one of the labels. The best solution is to use an application that is designed specifically for Gmail and its labels. I will point out a few of the best applications later in this chapter. Screencast 5.3 demonstrates how to create, search, and organize Gmail labels.
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SECTION 8
Server-Side Filtering As you’ve probably always checking your already figured out mail anyway for spam from prior chapters, filtering and to serve you I’m a big fan of email ads, it has some really filtering. The more our powerful tools for email application can autosorting, filtering, manage email for us, and managing your the less time we spend email. dealing with the Moreover, because this is nonsense and the more Creating a Gmail Filter done on Google servers, time we spend with you don’t need to have a the substantive email. Gmail is particularly computer plugged in for this work to take good at this. Because your mail is hosted on place. As much as I like Apple Mail’s rules, their web servers and their web servers are which are even more powerful than Gmail’s 220
server-based rules, Apple Mail’s rules only needs the rule, and (2) do something to the works if Apple Mail is running on a Mac email. somewhere. I know In checking mail for some users who application of a keep a Mac running filter, Gmail looks at at their home all the the sender, time for the sole recipient, and purpose of running subject line, similar Apple Mail rules. to iCloud’s serverYou wouldn’t need side filters. Gmail that with Gmail. In also can search the addition, Gmail’s contents of the online mail rules are message for words more powerful than that are (or are not) those offered by there. The ability to iCloud and other look inside the Available Actions for Filtered Email similar services. message for filter Similar to Apple Mail’s rules, there are two creation gives Gmail filters the edge over pieces to a filter: (1) determine which email iCloud. Gmail also lets you look at more than one criterion. I could look for messages 221
from Katie that don’t include the term Batliff. In iCloud server-side filtering, I can’t combine both of those into a single search. Apple Mail’s rules are better, but they are done locally and, again, require a Mac to be plugged in somewhere.
With a set of rules, Gmail could take much of the drudgery out of managing your email. I use these rules extensively in my Gmail accounts and always wish I had them on my other email accounts. Screencast 5.4 demonstrates creating and using Gmail filters to manage email for you.
Once I’ve selected an email through this filtering, Gmail gives me several options for what to do with it. I can archive the message, mark it as read, star it, apply a specific label to the email, or forward it to a specific person. I can also delete the message or mark it as spam. Likewise, I could mark the email important so Gmail knows where to categorize it when I receive similar emails in the future. All of this is done online by Gmail as soon as the email shows up.
Screencast 5.4 Gmail Server-Side Filtering
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SECTION 9
Gmail Stars Gmail stars are similar to Apple Mail flags but with more features. Gmail stars include different colored stars and little icons such as checkboxes, exclamation points, questions marks, and other symbols. To
cycle through the available stars, just keep tapping on the star. While I appreciate the expanded usage of multiple stars and icons, every time I’ve tried to use them in Gmail I eventually gave up on them. To go through
Setting Up Additional Stars in Gmail 223
and apply the various stars seemed more trouble than it was worth. This might just be me since I also barely use flags in Apple Mail. It may also be because I aggressively use labels whenever I use Gmail and have already created label versions of most of the star symbols. As an example, I have a “Needs Reply” label. I’m not sure this is a knock against Gmail stars so much as an endorsement of the various ways you can mark an email in Gmail as special. If stars make more sense to you than labels, go for it.
Gallery 5.1 Gmail Stars
This email is using a green check mark as its star. It is displayed to the right of the recipient’s name.
To add additional stars and related icons in Gmail, go to the General tab in Settings and scroll down to Stars and drag any stars you want to the in use row. Gallery 5.1 demonstrates Gmail stars.
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S E C T I O N 10
Google Labs In the Gmail Settings page there is a tab for Labs. This is the place where Google tries out new Gmail features. For example, they’ve got one Lab feature that lets you undo sending an email in the first few seconds after you send it. There is another Lab feature that lets you create canned email responses and send them without retyping. Others are more mundane, letting you further customize the interface. The Lab feature list is always changing and experiments appear and disappear, but if you use Gmail you should be checking this out regularly. Google Labs 225
S E C T I O N 11
Third-Party Apps for Gmail APPLE MAIL
treating it, more or less, like an IMAP client, Apple Mail is an option. When OS X 10.9 Mavericks first released, Apple Mail became even less useful as a Gmail client. However, Apple did issue an update to make Apple Mail more Gmail-friendly.
While there is a lot to like about Apple Mail, it is not a very good Gmail client. It isn’t built around Gmail and it shows. You simply don’t get all of the Gmail features listed in this chapter using Apple Mail.
I still think, though, that if you want to get the most out of Gmail, you should use an email client that embraces all of the Gmail features. That is not Apple Mail. There are, however, some good alternatives.
Nevertheless, a remarkable number of Gmail users use Apple Mail to run their Gmail accounts. It makes sense if you also have non Gmail accounts and don’t want to use multiple email clients. If you are just using the basic features of Gmail and 226
MAILTAB PRO
and the application also supports Google Talk. In addition to the drop-down menu bar, you can also expand it for the full Gmail experience with its own screen.
MailTab Pro (Mac App Store) puts your Gmail inbox in your Mac’s Menu bar. From there you can quickly check your mail without going to the browser. There are notifications available (if you go for that),
You can activate MailTab Pro with a keyboard shortcut (Control+G). There is also a keyboard shortcut to open the compose window (Shift+Command+M) that I find really useful.
MailTab Pro Screenshot 227
MAILPLANE FOR THE MAC
If you want a native Mac app for your Gmail instead of the browser, I recommend Mailplane. Mailplane (website) is a Mac app designed around giving you a native application for Gmail. It is currently shipping a third version and includes support for many Gmail features. It integrates with Google Calendar, supports up to 10 separate Gmail accounts, allows you to switch between them with tabs, and automatically uploads attachments to drop into the application to Gmail. It supports Macs with Retina display and even includes support for plug-ins (including AwayFind [website], covered in chapter 3).
On my Mac I prefer to run Gmail from the browser. It really is how Google intends you to use this service and, despite the drawbacks of being in a browser, I still think it is the superior experience for managing Gmail. If you were thinking about using Apple Mail instead, don’t. Apple Mail does work with Gmail, but it feels like a square peg in a round hole. The problem is Apple Mail simply wasn’t designed for some of Gmail’s more innovative features, such as inbox filtering, multiple colored stars, and labels. 228
The experience of using Mailplane isn’t all that different from using Gmail in the browser. Tapping the Mailplane icon in your toolbar opens a browser-like window with your Gmail account, as shown in the accompanying screenshot. I know a lot of Gmail power users who swear by Mailplane.
Mailplane for Gmail
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GMAIL APP FOR IOS
on the iPad and iPhone, I wouldn’t think twice about the decision to use the Gmail app. It’s free and I demonstrate it in screencast 5.5.
Apple Mail for iOS supports Gmail accounts right out of the box. However, the Gmail app from Google does a much better job with Gmail.
Screencast 5.5 The Gmail iOS App
Using the Gmail app, you can get those instant notifications (even customized to specific mailboxes) and take advantage of various Gmail services such as inbox categories, labels, stars, and other features that don’t work in the Apple’s Mail app. In my opinion, the iOS Gmail application is also more attractive than the web-browser version of Gmail. Google has traditionally had a reputation for not making particularly attractive applications, but I think the iOS Gmail app disproves that. For use of Gmail 230
S E C T I O N 12
Should You Use Gmail?
?
For a long time I was pretty judgmental about Gmail. The fact that they use the contents of my email to serve ads was just a nonstarter for me. Over the years however, my own expectation of online privacy has eroded and Gmail has become even more useful with some really compelling features. I no longer think it is a bad idea to use Gmail, but I do think potential Gmail users should go in with open eyes. Understand you’re getting a pretty great email service in exchange for
Google using your data to perfect its ever-growing advertisementserving machine. I explain further in my own workflow at the end of the book that after letting go of my Gmail hangups and using it for a few months while researching this book, I very nearly started using Gmail full time for my own personal email.
In answer to the above question, I think Gmail is a good service. If you decide to use Gmail, you should use it entirely with all of 231
its experimental features and innovations. What I mean is that if you are going to go in with Gmail and let Google collect your information, take advantage of all of the features so you get something in return. If you aren’t going to use Gmail’s best features, you’re better off opting-out and setting up a traditional IMAP account.
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CHAPTER 6
MORE EMAIL CLIENTS
When email first became a “thing”, there was a healthy competition among software developers to win your dollars with their email clients. Somewhere along the way, however, operating system manufacturers, such as Microsoft and Apple, began shipping email clients with a built-in operating system. Suddenly everybody had a competent email program that was free. This decimated the market for third-party email clients and for a very long time there simply was no competition to the free built-in options.
intentioned developers have begun releasing email applications to the market for the Mac, iPad, and iPhone. I attribute this to the fact that people are realizing that email is increasingly difficult to manage and they are looking for solutions. We aren’t just looking for an application that checks all boxes and supports IMAP, Google, or whatever your email choice is. Instead, we’re looking at applications to help us manage email better. In this environment, we just aren’t getting big full-fledged email replacements. We are also getting little speciality email
That, however, is changing. Over the last few years, several well-funded and well234
apps that just solve one problem really well and the full knowledge that you’ll be managing at least some portion of your email in a different application. The good news is that suddenly there is an influx of new third-party email applications, and a healthy competition exists. Innovative solutions to email can make our lives easier, and it seems people are finally swinging at this problem. This chapter points out a few of the most interesting third-party email solutions.
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SECTION 1
Mac Email Clients MICROSOFT OUTLOOK
Outlook (website) is Microsoft’s email, contact management, task management, and calendar application. This is Microsoft’s interpretation of the be-all and end-all application for Exchange users. Outlook works with Exchange Server 2007 or later. In late 2014, Microsoft released an update for Outlook (the prior version was 2011). Interestingly, this was the only All of that said, Outlook works just fine with traditional IMAP and POP accounts.
For a long time there was this bizarre holy war between Microsoft and Apple users. What a lot of Mac users didn’t realize is that there is a contingent of rabid Mac users inside Microsoft who love their Macs and spend every waking moment trying to make Microsoft Office for Mac a uniquely Mac experience while still retaining compatibility with its Windows cousin.
Outlook’s predecessor, Microsoft Entourage, had several quirks (including a single database for all of your email, 236
contacts, and calendars, which, if it got corrupted, may have led users to commit physical violence against their Macs) that kept me from recommending it to anyone. Outlook is much better. It does have a database file but if the database file gets
corrupted or trashed, your data remains and Outlook simply rebuilds the database. When it comes to reading and writing email, Outlook delivers. It includes the features we’ve come to expect. Custom signatures
Gallery 6.1 Microsoft Outlook 2014 Screenshots
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and address and calendar integration are all in the single application. Outlook goes above and beyond with email rules, giving users a similar experience to Apple Mail’s many ways to analyze incoming email and perform specific tasks on them. The application uses Microsoft’s ribbon interface, which a lot of people complain about. I don’t think it is that bad. I would, however, prefer that power users could give more customization to the ribbons so that the features we need most are available and others we don’t use can be sent away.
In terms of automation, Microsoft has always been good about including support for AppleScript and Automator. If you want to automate email using these tools, you’ll be fine with Outlook. The real use case for Outlook is if you are deep in a Microsoft Exchange network. Even though Apple Mail includes Exchange support, Microsoft’s Outlook goes deeper with Exchange features and support. Where Apple Mail includes Exchange support for the convenience of its users, Outlook was built around Exchange support. Many (but not all) of the features from Outlook on Windows make it over to the Mac in Outlook 2014 for Mac.
Outlook is also more stable and, in my experience, faster than its predecessor Entourage. Put simply, it feels a lot more like a Mac app. If you have attachments in an email message, selecting it and tapping the space bar gives you a quick look, like the rest of OS X.
This book is not going to cover the calendar, task management, and contact capabilities of Outlook except to say that they are there 238
and a workable solution, particularly for users on Exchange networks.
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POSTBOX
link from Dropbox and add it to the message.
Postbox (website) is probably the most popular third-party replacement for Apple Mail. It doesn’t try to copy Apple Mail but instead goes a different direction. One of its premier features is the ability to automatically link large files from your Dropbox (website) account into the body of an email message. Simply drag the file from Dropbox into the body of your Postbox message, and it creates a link. The recipients can then download the Dropbox file by clicking the link. This is also possible in Apple Mail, but it’s not as easy. Instead, you need to get the
Like Apple Mail and Gmail, Postbox supports the inclusion of conversations and threaded email discussions. Postbox will look through multiple folders to put these together and makes it easy for you to track an entire email conversation. I also like the clever way Postbox handles replies. Postbox has the ability to create a reply without opening a separate compose window. This lets you view the source message at the top of the screen and reply at the bottom. Alternatively, the compose window has a feature called Summarize that cleans up messy email threads and then replaces them with a digest of who said what. When composing a new message, you can use the search tool to find files for attaching to your
240
email without having to leave the compose window.
same keyboard shortcuts that you get with the native Gmail client. If you want to use
Postbox also includes support for Evernote (website). The connectivity between Evernote and Postbox is impressive. You can automatically use the message subject as a title and apply Evernote tags. Also, message attachments are sent over to Evernote and a direct link is created so you can go straight back to Postbox from Evernote to the source message.
Gallery 6.2 Postbox Screenshots
While in the end I think Mailplane is the goto application for Gmail, Postbox’s Gmail support is not shabby. It works with Gmail labels and even has a dedicated Important view that shows Gmail-identified highpriority messages. Postbox can also detect dates in your Gmail messages and add them to your calendar. Finally, it uses all of the
This is a sample of the way Postbox will summarize a conversation for reply.
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Gmail in addition to other IMAP accounts, Postbox does a good job at managing both. Postbox also has its own tagging support. You can assign a message to a particular tag, and it is applied to all the other messages in the conversation. This works with Gmail or any other standard email account in Postbox. There is a version of Postbox for Microsoft Windows, if that’s your thing. If you are a Microsoft Exchange user, move along. Postbox does not support Exchange email. I spent significant time using Postbox in preparation for this book and was more impressed than I expected to be. It really is nice seeing that third-party mail application developers are bringing some innovative solutions to email.
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MAILMATE
exception. MailMate’s does render HTML in incoming mail.
MailMate (website) is an IMAP and Gmail email client. If you use Microsoft Exchange or Gmail (or even POP), it won’t work for you. The interface is entirely text. As far as I can tell, there is not a single icon in the entire application. There isn’t even any formatting in the application for composing emails. This application writes email in plain text. (There is an exception if you know how to write in Markdown and if you don’t, there is a MacSparky Field Guide on Markdown [iBooks Store] to fix you up.) For some people the plain text is a selling point. I’ve spent plenty of time talking to people about the merits of plain text (website) in any medium and email is no
So why on earth would you ever want to use this application? For one reason, it’s fast. Because it is largely working in plain text, messages display and can be composed very quickly. Also, MailMate has some very powerful search criteria. Where most email applications limit search criteria to things such as the recipient and sender, MailMate goes completely crazy with this. You can search for a single word embedded inside the email header. You can search for quoted or unquoted text. Forensic computer researchers who need to look through vast bodies of email for that one smoking gun would absolutely love the search tools available in MailMate.
243
MailMate has been getting a lot of development love recently and they are funding a new version 2.0 which promises to keep that same under-the-hood power but also add a better interface. MailMate could come out of this next update as the go-to application for Mac power users.
Gallery 6.3 Mailmate Screenshots
In version 1.0 of this book, I had a great analogy of MailMate to a 1970s-era Buick: MailMate isn’t very pretty but man does it have a lot of power under the hood. However, that analogy seems to be falling apart.
244
AIRMAIL
There are built-in filters to show, for instance, all messages with attachments. In that case, you just tap on the Paper Clip icon. It also supports conversation view and lets you organize by subject or person.
Airmail (Mac App Store) (website) is another upand-coming third-party Mac mail client. Airmail supports Gmail, iCloud, Yahoo, AOL, and generic IMAP clients. There is no Microsoft Exchange support.
Gallery 6.4 Airmail Screenshots
For a third-party, independent application, Airmail’s got a lot under the hood. The user interface is very attractive and immediately useable. I found it very easy to manage my email from inside Airmail and really like the little touches, including the very satisfying sound effects as I worked through my mail.
245
Airmail includes great support for keyboard shortcuts (including Gmail shortcuts) and even lets you write your email using Markdown, which always makes me happy. While it is still early days, AirMail is an application that I could see myself someday using full time.
246
UNIBOX
Gallery 6.5 Unibox Screenshots
Unibox (Mac App Store) (website) takes an entirely different approach to email. Instead of organizing your email chronologically, it organizes your email based on your contacts. Once you set up Unibox, you will see a list of your contacts on the left side of the page. If your contacts have photographs in your Contacts app on your Mac, that picture will show up in the mail application. Clicking on the contact displays a list of messages with that contact.
While I like the idea of a different way to organize email, Unibox wasn’t practical with the large volume of email I manage. As this book goes to press, Unibox is new and I’m keeping the app on my Mac to see where the developers go with it.
There are some other innovative features in Unibox. For example, you can see a list of all attachments exchanged between you and another person. 247
SECTION 2
iOS Email Clients MAIL PILOT
Rather than fight the inclination to turn your inbox into a task list, Mail Pilot (iOS App Store) (website) embraces it. Mail Pilot is a mail application for the iPad and iPhone (with a Mac app on the way) that incorporates task management into your mailbox. When a mail message arrives in Mail Pilot, you can archive it, file it away with the project, or even file it away for a specific future date. It allows you to defer an incoming email so you don’t see it for a certain number of days.
One of the underlying themes of this book is that your email inbox is not your task list. Your inbox is illsuited for this purpose and ends up costing you a lot of time and making you act like a flake. Mail Pilot’s developers attempt to turn this fact on its head.
Say your coworker asks you to return his Brony T-shirt (Wikipedia) at the staff 248
Gallery 6.6 Mail Pilot Screenshots
meeting next Wednesday. You could push the email back so you don’t see it until then. In order to make all of this happen, Mail Pilot is required to add several mailboxes to your IMAP account and constantly communicates with servers to make sure it keeps up with what email it should display and which it should hide. There is a growing movement of apps giving you the ability to defer email to some future date. Mail Pilot is probably the best of them. If you find yourself constantly overstuffing your Action box, deferred mail is not a bad idea. I’ve started using deferred email in some instances but I do it through the SaneBox service.
249
DISPATCH
of different ways to put that message somewhere else. As I write these words, there are 16 different available actions for an email message ranging from copying the message to your clipboard to inserting them into some other application, such as Evernote, OmniFocus, Fantastical, or a big list of others. If you’ve got a preferred “thing” you like to do with your email messages outside of the email application of choice, Dispatch streamlines the process of getting it there.
As you’ve read throughout this book, I’m a big fan of letting the robots in our electronics take the tedium out of email management for us. One aspect of this is getting information out of email and into applications where it is better suited. This is more challenging on the iPhone and iPad because iOS doesn’t make it as easy to share data between apps as the Mac OS does. This is the problem that Dispatch (iOS App Store) (website), an iPhone-only mail application, attempts to solve.
Dispatch also gives you a lot of options for other formats of data. For web links, you can open them in any one of a variety of supported iOS browsers (such as Safari, Chrome, and others), you can send the link to 1Password, or you can read it later on services such as Pocket (website) or Instapaper (website). The application also
Dispatch focusses on action-based email management. When you select an email message in Dispatch, the app gives you a lot 250
gives you multiple app destinations for dates and times, phone numbers, emails, and addresses. There is a Quick Action bar across the bottom of a message from where you can perform a variety of actions on an email including marking it as read, flagging the message, archiving it, filing it in a different folder, or deleting it. In Settings you can assign a specific folder to Quick Move. When you do that by tapping and holding on the Down Arrow in the Quick Action menu and dragging it to the left, it sends the email to the folder without requiring you to navigate a folder list. I use this for my Action folder and it helps me make quick work of the inbox. If you drag the Quick Action bar further, you can immediately archive a message. (There is also an Undo button that briefly appears so you can fix any mistakes.) Once you open a message, there is an Action icon that enables you to invoke all of the sharing features I covered above. The interface for this is nice, showing just icons for the applications you’ve turned on. Tap on an icon and the 251
Gallery 6.7 Dispatch for iPhone Screenshots
message gets delivered to the third-party application. For a lot of applications this means you’ll get taken out of Dispatch and taken into the third-party app for additional processing, which throws some people off.
its own built-in text snippet feature. The implementation lets you search your snippets as you use them, which is nice. Dispatch has its own search tools. You can narrow your search to specific fields including the sender, recipient, subject line, and message contents. Dispatch supports multiple email protocols such as IMAP, Gmail, iCloud, Yahoo, and even AOL.
One really clever feature is an automatic salutation. When you reply to a message, Dispatch starts the email for you. If, for instance, I’m replying to an email from Kourosh, the email starts Hi Kourosh. It grabs the first name from the source email and automatically inserts it. You can turn this off, but I really dig it. It makes replying to email just a little bit easier. Also, because I often use Siri Dictation for email replies, I don’t have to worry about Siri choking on my correspondent’s name.
While Dispatch really isn’t the full-fledged email client you would want to use to replace something such as Apple Mail or the Gmail application, it is a powerful tool for helping you manage an active inbox and it gives you features that simply aren’t available in the more full-fledged email applications.
Dispatch can use TextExpander (iOS App Store) (website) text snippets and also has 252
ALTAMAIL
into AltaMail and attach it from inside the application.
Most iOS email clients focus on fixing one or two problems with email. AltaMail (iOS App Store) (website) is more ambitious. It seeks to give you a soup-tonuts email client replacement with some features you won’t find in Apple Mail.
That’s not all. AltaMail also has mail rules. I’ve talked about rules at length already in relation to Apple Mail and Google Mail. I have to admit I was a little shocked when I discovered an iOS developer had the moxie to add a full-blown rules system to an iOS mail application, but that’s exactly what AltaMail did. Swiping left to right on any email message in AltaMail gives you the option of creating a rule based on it. Filters exist for the the sender, recipient, copies, and subject line. Once an email satisfies the AltaMail filter, you can send it to a folder, delete it, forward it, set a flag, or mark it as read. Imagine opening AltaMail on your iPad or iPhone and having it automatically sort and file your email for you. It is possible. Another task AltaMail can perform
A common complaint about Apple Mail is the backward way it goes about attachments.While you can attach pictures and videos to an email message from inside Apple Mail, any other type of attachment requires you to find a separate app that supports that file type and includes an option to share the file via email. AltaMail lets you attach files from cloud storage, including iCloud, Dropbox, Google Drive, and SugarSync, from inside AltaMail. In addition to this, you can save a file locally 253
Creating a Mail Rule in AltaMail
Email templates are prewritten emails AltaMail saves and lets you send over and over again. Let’s say you are the office nerd (like me) and your coworkers seem to have a lot of trouble remembering the WiFi password. You could make a template email with instructions of how to login, the network name, and password. Then every time someone asks you for it (again) you could fire up AltaMail on your iPhone and send off the WiFi email without ever having to type it again. Tying this feature to AltaMail’s mail rules, you could even automate it. If an email arrives from Lars with the word WiFi in the subject line, send the WiFi email template.
on a filtered message is the creation of a template reply, which leads to the next interesting Alta Mail feature.
There are a lot of additional features in AltaMail including Smart folders, multiple account support, a unified inbox, multicolor flags, and the ability to view the raw source 254
of an email, which is a feature I’m not aware of on any other iOS mail application. AltaMail seeks to provide a desktop-class email experience on iOS and succeeds on several levels. Apple sets the tone for app development on its platforms and one of their most fundamental design principles is that the developer sweats little details and makes hard decisions about what features to include. This provides a much more streamlined computing experience that lets the rest of us get on with our work. AltaMail ignored this lesson and instead provides you a big mail application that has more features, bells, and whistles than you’d ever expect on a mobile email client. If you find yourself pining away for this experience on your iPad and iPhone, AltaMail will make your day.
Gallery 6.8 AltaMail Screenshots
The AltaMail compose window. 1 of 12
255
TRIAGE
Gallery 6.9 Triage for iPhone Screenshots
Triage (iOS App Store) (website) is not a new email client but instead an email utility. The app supports Gmail, iCloud, Yahoo, and other IMAP accounts. (There is no Microsoft Exchange support.) Triage displays each email in your inbox as a card. Triage doesn’t show you your folder structure, your archive, or anything else. For each email card, you can flip up to archive (or delete or mark as read), flip down to retain and keep the message marked as unread for later, or tap on the message to reply. If you’re out and find yourself with five spare minutes, you could very quickly go through your email inbox this way. Triage doesn’t solve all of your email problems, but it does make managing your inbox much easier. I like the simplicity of Triage.
256
DRAFTS
Gallery 6.10 Drafts for iPhone Screenshots
In a similar vein, Drafts (iPhone Version in iOS App Store) (iPad Version in iOS App Store) (website) is a text authoring tool with versions for the iPhone and iPad that can serve as an email utility. Specifically, Draft does a great job of capturing text. When you open Drafts, it immediately has a cursor and is ready to go. You can then quickly write a message using the keyboard or voice recognition with Siri. Drafts supports TextExpander touch (iOS App Store) (website) so you will have the benefit of all your text snippets at your disposal. When you’re done, you can send the email directly from Drafts. You can even automate this to routine correspondents. I love writing emails in Drafts because Drafts sends email without opening your email application.
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CHAPTER 7
FIGHTING SPAM
SECTION 1
The Spam Problem THE SPAM PROBLEM
Python sketch (YouTube) involving a restaurant where all the items on the menu included the canned meat. (As an aside, I grew up eating SPAM often, which further explains my complete disdain for spam email.) Geeks love Monty Python and the word spam was frequently used in the bulletin-board days of the Internet. It follows us to email and now is the common word for all of that terrible email that tries to pull you away from the things you love.
Junk mail has always been a problem. Even before we had email, junk mail was making us angry. At least with the type of junk mail that goes through the post office, merchants have to pay for postage, which places some constraint on the amount of junk mail we receive. Imagine that instead they could mail as much junk mail through the postal system as they wanted without cost and you’ll get why email is such a problem.
Experts estimate 80-85% of all email sent is spam. Think about that one for a moment: 17 of every 20 emails sent to you are spam. I
The etymology of spam is actually kind of entertaining. It all started with a Monty 259
guess that answers my question earlier about what would happen if direct mail marketers didn’t have to pay postage.
spam. Moreover, a lot of times these emails aren’t even solicitations but instead attempts to get you to click something that installs the bad guys’ robots on your computer so they can use it without you knowing in order to send out even more—wait for it—spam.
Not all spam is created equal. Most of it is unsolicited garbage. This is the email that comes from the darkest corners of the Internet trying to sell you pornography, sexual Another type of spam, performance drugs, and cures sometimes referred to as bacn for male pattern baldness. This (and pronounced bacon), isn’t spam isn’t sent to you for any as malicious as spam. This is reason other than there is a big the email you get from online list of email address vendors you have voluntarily 80-85% of email is spam. That’s a
Pac-Man-sized portion of our email. somewhere and you’re on it. If done business with. I buy dress you click on any of these shirts from the apparel emails (even to unsubscribe), you’re telling company Lands’ End. As a result, they send the bad guys they’ve found an email address me a lot of spammy sales emails. Lands’ End with a human on the other side and isn’t some stranger to me or a criminal encouraging them to send you even more enterprise but instead a legitimate vendor 260
My Apple Mail Unsubscribe Smart Mailbox
that wants to exchange their stuff for my money. This type of spam is more avoidable. If I unsubscribe from the Lands’ End email list, they will stop sending me solicitations. But because I like those 30% off sales, I deal with their email.
unsubscribe. I even have an Apple Mail Smart Mailbox that looks for any email containing the word unsubscribe. If bacn spam is still bothering you, try a service like Unroll.me (website). The service scrubs your email for you. In addition to helping you unsubscribe, the service combines multiple emails into one single summary email instead of flooding your inbox.
Using the unsubscribe button on bacn-style spam works. If you unsubscribe from legitimate companies, you usually never hear from them again. I am fastidious about this. If an unwanted email arrives from someone I’ve done business with, I 261
SECTION 2
Fighting Spam SPAM SOLUTIONS
between the people who send spam and the people who block spam will never end and as users, we do need our own solutions for spam that gets through the system.
The real solution to spam is to put your computer and email services to work for you. Gmail’s antispam filters are widely recognized as some of the best. Some people use Gmail just because of their spam filters.
One solution to spam is mail rules. If you unsubscribe to a vendor and they still send you mail, create a mail rule to automatically delete anything they send you. Another solution is to use an online service such as SaneBox (website) to help you out. SaneBox has a feature called the SaneBlackHole that does a great job of making sure you don’t see spam from the same source more than once. If you’ve still
Google isn’t alone in this regard though. Apple also applies its own spam filters to iCloud mail, and any other self-respecting email service provider will also look to keep spam out of your life. The technologies they use to filter spam are actually quite sophisticated. But the cat-and-mouse game 262
got a problem with spam, install SpamSieve on your Mac.
spam and phishing emails. It includes whitelist support so you can guarantee receiving messages from people who are important to you. It automatically adds all of your previous correspondents and people in your contacts database to the whitelist so you should never have a problem with false positives. The application color codes spam messages so you can quickly focus on those that may be borderline and entirely ignore those that clearly are not.
SPAMSIEVE SpamSieve (website) is the premier spam software for the Mac. This has been true for a long time. Every few years I survey the field of other spam applications on the Mac and every few years I come back to the conclusion that this is a one-horse race.
One of the common tactics for spammers is to embed their message in an image. SpamSieve looks inside attached images and runs its own algorithm to determine whether or not it is spam. So long as you are using an IMAP-style mail server, once SpamSieve deals with an incoming message on your running Mac, it will also disappear from your mobile devices.
SpamSieve works with most email clients on the Mac and installs a set of plug-ins that does all the hard work of filtering spam for you. SpamSieve learns and adapts to your email so after a little use, it blocks nearly all 263
If you’re having trouble dealing with spam on your Mac, go directly to SpamSieve and install it on your Mac.
Gallery 7.1 SpamSieve Screenshots
264
CHAPTER 8
EMAIL SECURITY
SECTION 1
Why Email Security Matters Take a moment to think about the kinds of email you have on your iPhone. There is a record of every private electronic conversation you’ve had with everyone in your life. There are probably confirmation emails from online services with your login information and even possibly passwords. You also likely have some emails to your partner giving the login and password information for
To: Josephine From: Napoleon Subject: Bank Password?
some online accounts you’d prefer not to share with strangers.
Once the bad guys get access I’m heading to Waterloo to your email, they’ve got tomorrow and need cash but the private messages and photos. bank won’t let me login. I They know about your favorite thought it was “shorty123” but online retailers and often what that’s not working. What’s the your account numbers are. password again? They know where you bank and who you work for. They’ve -Boni also got access to information about your job and, likely, some of your work documents. 266
They can use all of this to harvest your own email contacts and reach out to your friends and co-workers in attempt to hack their email accounts using your name. Email security should be a big deal for everyone. This chapter is going to help you avoid making the most common email security mistakes and show several ways to improve email security, including encryption.
267
SECTION 2
Basic Email Security USE A REAL PASSWORD
password system. 1Password also paid for this book so what are you waiting for? Go get it.
The security of your email is important. Don’t use unsafe passwords such as your birth year, ABCD, or— believe it or not—password. (Did you know that password is the most common password?) I create real passwords with 1Password (iOS App Store) (Mac App Store) (website). 1Password is on multiple platforms and creates and stores advanced passwords for you. The team at 1Password works hard so you can have a responsible
10 Most
Common Passwords
In addition to creating a secure password for your email, don’t forget to change it every once in a while. Whenever the clocks change in the spring and fall, I change all of my major passwords (including email). Email is too important for soft passwords. It is remarkable how much more difficult you can make it for hackers with a secure password. 268
Password:
abc
Time to Hack:
0.000004394 seconds
Password:
aP#ZI&#LFAIadi;#@oP
Time to Hack:
45 quintillion years
The Cautionary Tale of
Mat Honan’s Epic Hacking
Did you know quintillion was a word? Neither did I. Source: HowSecureIsMyPassword.net (website)
Mat Honan is a well-respected writer for Wired magazine and no stranger to technology. In 2012, hackers broke into Mat’s Amazon, Apple, Twitter, and Google accounts by taking advantage of a series of vulnerabilities in these companies’ services. The hackers were very clever. At the time, Apple did not have twofactor authentication for its accounts and had a policy that allowed its customer service representatives to issue new passwords to users over the telephone, which could confirm a billing address and the last four digits of their credit card. (Not surprisingly, that is no longer the case.)
The 1Password New Password Generator
The hackers got Mat’s billing address by searching the records of his personal website. To get the last four digits of his credit card, they called Amazon, told them they were Mat, and asked to add a credit card to the account. At the time, 269
TWO-FACTOR AUTHENTICATION
Two-factor authentication adds an additional layer of security by requiring a second validation. Most commonly this is done by requiring a password plus a verification code delivered to the user’s mobile phone. So if the bad guys get your password, they could not get access to your account to change your password unless they also had a six-digit code sent to your phone. This makes hacking your account a lot more difficult.
For the longest time, computer security involved a username and a password. Usernames aren’t well protected and often are as simple as an email address or your name. So in order to break into your email account, all the bad guys really needed was your password. Just finding one piece of data to get access to a person’s email account just isn’t good enough. This was most dramatically demonstrated in the epic hacking of Mat Honan, explained in the sidebar.
Both iCloud (website) and Gmail (website) support two-factor authentication, and I strongly recommend enabling it. Two-factor authentication is a relatively new thing, and there still are occasional problems with it. If you use the phone message method and lose your phone, you could end up getting locked out of your own account. On balance, however, I’d much rather have to jump
Service providers such as Apple and Gmail realize how inherently insecure accounts are that only require a password. In the last few years, there have been several attempts to remedy this. One of the best methods is two-factor authentication.
270
through additional hoops than make it easier for the bad guys to hack me the way they did Mat Honan.
271
SECTION 3
Avoid Phishing Email phishing is the act of sending a false email that looks as if it’s from someone the recipient trusts and asks the recipient for some personal information from which the phisher can benefit. It’s shameful and the practice is not going away. As an example, I get an email nearly every day from hypothetical PayPal (as opposed to actual PayPal). The email is always addressed to “Dear User”. It is never addressed to me personally. The email always tells me there’s something critically wrong with my email accounts, and it’s going to cost me a lot of money if I don’t fix it right away. The email
then tells me I can solve all of these dreadful problems by just tapping a link in the email and providing necessary details such as my Social Security number, the name of my bank and account number, my mother’s maiden name, my blood type, the vehicle identification number from my car, the location of my extra house key, and—of course—a list of all my Boy Scout merit badges. Phishing emails prey on people’s good nature to believe that when the email says it’s from PayPal, Apple, Amazon, or your bank, that it actually is from that company. 272
The crooks behind phishing email scams get only more sophisticated as time goes on. It used to be that all phishing emails had a domain listing with some foreign country that clearly did not seem appropriate for that company. However, the crooks have figured out ways to spoof the emails so they look as if they are actually coming from the indicated company. Another telltale sign is that the email is addressed to a generic name such as Customer or User. If you receive an email from your bank and it’s not directed to your name specifically, it is a phishing email. Rarely are phishing emails addressed to your name directly, though nowadays there are some that do.
Sample Phishing Email
Here is a phishing email I received while writing this chapter. Note that it is addressed to “User” instead of me directly and the sense of urgency it conveys. “The Team” includes a link that would lead me to a website looking a lot like the real PayPal and asking for all of my account information. Shameless!
This book cannot offer you a magic solution to avoiding phishing emails. There is no app, service, or plug-in that will make this go away. Spam filters, discussed earlier in 273
chapter 7, will help capture a lot of this type of email. However, phishing emails still will make their way through your filters on occasion. Your best defense is your wits. Whenever someone sends you an email asking for any kind of information, red flags should go up and klaxons should go off in your head.
Internet through an independent search. I know this sounds paranoid but, sadly, it is not.
If you have any doubt about an email, pick up your telephone and call PayPal or Visa or your bank. Talk to a human on the telephone, tell them what you received, and ask them if there is any issue with your account. Under no circumstances should you ever click on one of these emails until you’ve first verified with a human that it is for real. As an aside, when calling these people, never use the telephone number provided in the suspect email. Look on the back of your credit card or look it up on the 274
SECTION 4
Email Encryption Even with great passwords and the best security habits, email still has its security vulnerabilities. You are creating a message of digital words and sending it up into the Internet where it gets passed around through several servers before landing in someone else’s inbox. Security holes at any point of that journey, from the Starbuck’s WiFi to the Internet mail servers to the recipient’s mailbox, may allow others to read your email. This section
explains how to protect and encrypt your email. A long time ago (well maybe not that long ago), people would send letters to each other and seal the envelope with a wax seal. Delivery of a letter with the sender’s seal intact assured the recipient that the sender actually wrote and sent the letter and was unread in transit. Email encryption looks to bring a wax seal to your Mac.
275
PGP
with writing email: How do your correspondents encrypt a message to you without knowing your own secret encryption code so they (or anyone else) can read all of your mail? PGP solves this
Pretty Good Privacy (PGP) (website) is one of the original commercial email encryption solutions. PGP, now owned by Symantec, offers several products including PGP email encryption. There is a unique problem faced
Screencast 8.1 The Mechanics of Public/Private Key Encryption
276
problem with public and private key encryption.
both their PGP email encryption and wholedisk encryption products. However, Apple has since improved FileVault (which handles whole-disk encryption) to such an extent that I let my PGP subscription expire. For email encryption, rather than pay for a PGP license, I’m now using the open-source alternative to PGP, GNU PrivacyGuard (GPG).
When you set up a PGP account, you get a private encryption key, which you keep for yourself, and a public key, which you share openly. Anyone else with a PGP account can use your public key to encrypt a message for you. Once they encrypt the message, the text converts to unreadable gibberish. Nobody can unencrypt the message except you, using your private key. Screencast 8.1 demonstrates how private and public key email encryption works. PGP is a paid service with options for individual and larger enterprise accounts. It can work through Apple Mail and several other email clients. In a corporate environment, PGP is probably the right solution. I used to own a PGP account for 277
GPG
Gallery 8.1 GPG Encryption in Apple Mail
GNU Privacy Guard (GnuPG or GPG) (website) is an open-source mail encryption project. It uses the same type of public/ private key encryption that PGP does. Moreover, they’ve developed some great tools for implementing GPG on your platform of choice. It is very easy to set this up for Apple Mail on the Mac using GPG for Mail (website). This is a custom installation of GPG that works right inside Apple Mail. The installation process walks you through setting up your public and private keys, and because everything works inside Apple Mail, adding encryption to your email is easy.
increasing the likelihood that you’ll be able to locate public keys for your correspondents and successfully send encrypted email. Gallery 8.1 demonstrates using GPG in Apple Mail.
There is a lot of momentum behind GPG encryption in that it is free and easy to install and use. As a result, there are a lot of people signing up for this encryption,
Encrypted email is much more secure than not. This, however, does come at a cost. All of those services I’ve written about in this 278
book that help you manage and sort email as it arrives largely won’t work for encrypted email. Furthermore, even though GPG has greatly simplified the process of sending encrypted email, it still adds steps and time to every email you send. I don’t recommend encrypting all email you send, but for those instances when encryption is more valuable than the inconvenience that comes with it, you should at least have that option.
(This works in just about every application on OS X for Mac.) Then click Save as PDF… and in the next dialog box, click Security Options.... There you can insert a password and save your file as an encrypted PDF. Then send the encrypted file to your recipient as an email attachment. Provide your friend the password through some Screencast 8.2 Encrypted PDFs on the Mac
ENCRYPTED PDF Another way to send encrypted messages is done via encrypted PDF attachment. This involves the creation of your message as an encrypted PDF file and attaching it to an email message. You can do this anywhere in the Mac OS using the built-in PDF tools. To do so, click on the PDF button in the lower-left corner of the Print dialog box. 279
means other than the enclosing email, and they can unencrypt it on their end. The security isn’t as complicated (or as strong) as the PGP or GPG solutions but in a lot of cases it is good enough. Screencast 8.2 demonstrates how to do this on the Mac.
280
SECTION 5
The Limits of Email Privacy Even if you follow every recommendation in this book about protecting your email, never forget that when it comes to email, for every sender there is a recipient. Even if you do everything right, if your recipient keeps your email message on an unlocked iPad, the next person to sit in your friend’s airline seat after she leaves it in the seat pocket can read all of your email. Because email is a communication, there are limits to what you can do about it.
program (Wikipedia). It is likely that the United States isn’t the only country conducting this sort of data collection. As this book goes to press, there are even more revelations about how sophisticated government snooping is. In Russia, the Kremlin is so fed up with the leaky nature of email that they’ve reverted to using typewriters (website). At some level, this is debilitating. We spend so much time and effort trying to protect our privacy, apparently to no avail. I don’t have answers to what we should do (or even think) about government snooping, but I
In 2013, it became public knowledge that the United States government was capturing a lot of private email through its PRISM 281
still believe strongly in email security. Even if your correspondents are sloppy and the guys in black hats are reading our email, good email security habits can keep a lot of other people out. Finally, accept that these communications aren’t entirely secure and think about what you write in an email. If you’re not comfortable with the contents of your email on the front page of your local newspaper, think really hard before sending it in an email.
282
CHAPTER 9
ARCHIVE
SECTION 1
Apple Mail Export Whether you are using a native mail client down from the cloud. There are several such as Apple Mail or a web-based solution tools to pull this off. such as Gmail, there One of the easiest ways may be performance or Screencast 9.1 Exporting Mailboxes in Apple Mail to make an extra copy privacy reasons for you of your email files from to save portions of Apple Mail is the your email to an Mailbox→Export archive. Apple Mail Mailbox... Menu bar will slow down with selection. You can large libraries and export a mailbox to an while Gmail is great, external drive and have there is something to your very own backup. be said for pulling a There is no way to copy of your emails analyze or search the 284
emails in that database short of importing it back into Apple Mail, but if you are looking for a quick and dirty way to make a copy of your Apple Mail folders, there is none quicker or dirtier.
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MailSteward For a long time, MailSteward (website) has been the go-to solution for email archives on your Mac. MailSteward will copy your entire Apple Mail email database (including attachments) to its own separate database. You can search the MailSteward database at will to find your old messages when you need them later. Moreover, because you’ve placed all of your email in a separate searchable database, you can delete large portions of your existing email database, improving performance.
Speaking of performance, MailSteward has the same challenges as Apple Mail when the database gets too big. It can slow down the more demands you place on it. In my experience, when a database starts approaching 100,000 messages, you’ll need to make a new database. MailSteward Pro will save to a more robust MySQL database that will give you more breathing room. However, I doubt this will be necessary for many individual users. There are several settings in MailSteward so you can tell it what to backup and when to do it. You can select specific mailboxes, 286
accounts, and time periods. MailSteward can also automatically delete emails as it archives them from your database. Be warned, however, MailSteward is not designed to put messages back into your email library.
Gallery 9.1 Screenshots from Mail Steward
from a coworker gets a Work tag. That can make future searches much easier.
I’ve owned MailSteward for years, but I’ve never been able to bring myself to actually delete messages from my email database after archiving them. I’ve never felt as if my Mac couldn’t keep up with my email database (which is now at 115,000 messages). I suspect this is a combination of software improvements Apple has made with OS X for Mac and Apple Mail and my
MailSteward has several useful features including scheduling, which will automate the archival process, and tags. MailSteward will use rules to add tags for the MailSteward database upon export from Apple Mail. For instance, I could add a tag that any emails 287
obsession with getting a new Mac every two or three years, but I’ve never had the kind of performance problems that required me to delete old emails. Nevertheless, having an external copy of my email database seems like a good idea, and MailSteward does this job reliably. Gallery 9.1 includes several Mail Steward screenshots.
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Email Archiver Email Archiver (Mac App Store) (website) is a more recent arrival in this space. Created by Ironic Software (website), Email Archiver takes a different approach. Instead of rebuilding your email in a searchable database, Email Archiver exports all of your email as PDF files in hierarchical folders. These folders are organized by date with the same structure as your email database, and Spotlight on your Mac will search the entire database for you. If there are message
attachments, Email Archiver will create a separate folder with the email name holding all the attachments. Because it is a PDF export, this app is also useful for archiving just the emails from a project. Gallery 9.2 includes some screenshots but there really isn’t much to this application. You run the archive and then navigate the nested folders to your desired folder. I really like the idea of an email archive not tied up in a database but instead a list of 289
PDF files. I wrote about this a lot more in Paperless (iBooks Store) (website), but the less we rely on some proprietary format for our data, the better. Indeed, I like Email Archiver so much that it has replaced MailSteward for my email archiving needs.
Gallery 9.2 Email Archiver Screenshots
Email Archiver has one of the simplest user interface buttons I’ve ever seen.
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Archiving Gmail Archiving web-based email is a good idea. Companies such as Google understand backup, and I can’t imagine them losing all of your online email, but why leave this up to them?
purpose of making an archive. If you do that, any of the options already covered in this chapter would work.
Google has faced this issue head-on with the Google Takeout service, that lets you download your Google email and data.
If you are heavily invested in the Google lifestyle, try using CloudPull (website). CloudPull pulls down all of your Google data for a local backup. It is really good at copying your Gmail, including the ability to pull messages or Gmail labels into Apple Mail as mailboxes. It also imports your Google contacts, calendars, and documents from Google Drive. Out of the
Another option is to use a local client. Even if you prefer using Gmail through the website (like I do), you can still occasionally fire up a local client, such as Apple Mail, and connect it to your Gmail account for the 291
box, CloudPull backs up your Google data every hour and is an excellent solution if you’ve got a lot of data on Google servers.
a Gmail or Yahoo mail account. These aren’t active accounts but simply an online destination for copies of important emails they’d like to keep. I get the convenience of this, but I prefer email archives on hard drives that I own and control. I’d recommend the other approaches covered in this chapter.
Another option for backing up Gmail is Backupify. (website) Backupify can back up Gmail (and other Google data. You can do a backup of your gmail to your local computer. The service also includes an option to password protect .zip files of your email.including the ability to password protected .zip files. BACKING UP TO AN ONLINE ACCOUNT Another method some people use for backup is sending a blind copy of all their emails to 292
SECTION 5
Saving Individual Emails Archiving all of your emails is great, but sometimes you just need to save a single email to PDF. That is painless on the Mac. With Mavericks, Apple added a new keyboard shortcut to Apple Mail,
Control+Option+Command+P, that saves the email to PDF. (It also will work with multiple selected emails.) Gmail also has a mechanism for saving an email to PDF. If you want help figuring out what to do with those email PDFs after export, read my Paperless Field Guide (iBooks Store).
Screencast 9.2 Printing an Email to PDF
293
CHAPTER 10
EMAIL WORKFLOWS
At this point in the book, you are already an email ninja. You’ve also figured out that there is not any one be-all and end-all solution for email. This chapter pulls it all together where I share my own personal email workflow.
that makes you nuts, go here in your browser (website) and you can download all the audio files for import into iTunes.
I also conduct audio interviews of some of my brilliant friends about how they deal with email. I chose people from many walks of life for these interviews. There are doctors, educators, IT specialists, writers, directors, actors, and producers. They all have large email demands placed on their time, and a lot of them use different email systems and technologies to cope. They are all wicked smart. There is a technical limitation with iBooks that will stop playing the audio file in these interviews when you change the page. If 295
SECTION 1
My Email Workflow MY EMAIL ACCOUNTS
that I share with friends and family and manage my personal correspondence.
I'm a man of many mailboxes.
My law firm uses Microsoft Office 365 including their hosted Exchange. As such, everyone in the firm has Microsoft Exchange email, calendar, contacts database and all the other Exchange-y bits that come with it.
There are several aspects of my life that I would like to think stand independent of one another. I'm a dad. I'm a geek. I'm a lawyer. For my personal email, I use an iCloud account. Years ago I had this on a local Internet Service Provider email account but moved it to an Apple @mac.com account. Then Apple transitioned @mac.com to MobileMe and now, most recently, they've transitioned to iCloud. Regardless, this is the email account
On the geek side, I have multiple email addresses. I have an email address related to the Mac Power Users podcast, several related to MacSparky, including feedback and other pieces relating to the publishing 296
My Email Accounts
business. I've set up all of those accounts to point to the
[email protected] account. If you send me an email from any of my tech related goings-on, it is going to get automatically forwarded into that account. At the end of the day, I'm managing three important email accounts in my life.
traditional IMAP account (although I spent some time with that account as a Gmail account, explained later). My personal email is through iCloud. My primary email application is Apple Mail for both the Mac and iOS. While a lot of
Each of these three accounts use different technologies. The day job account uses Microsoft Exchange. MacSparky uses a 297
geeks, myself included, have poked fun at Apple Mail over the years, the fact is Apple has improved this product a great deal and added features that I find extremely useful, such as VIPs, better keyboard support, an outstanding set of mail rules, Smart Mailboxes, and several of the other features I covered in this book.
every day but instead I primarily use it when I get busy, know my inbox is filling up, and I don't have time to deal with it in full detail. Because I use SaneBox, my inbox is already filtered and a lot of emails aren’t in Dispatch for processing. FLIRTING WITH GMAIL
On occasion, I've been known to use third-party applications, particularly on iOS. I like the way iOS mail tools have cropped up to solve little email problems without trying to replace Apple Mail entirely. One of the best I've encountered for this purpose is Dispatch. It lets me quickly filter through the emails in my personal and MacSparky accounts and reply or set them aside for further processing. I don't use Dispatch
In the process of writing this book, I spent a lot of time using applications that I covered in chapter 6 (and quite a few more applications that didn't make the cut). I was most interested in Gmail. I started this journey inclined to switch to Gmail permanently. A lot of friends that I 298
know and respect use Gmail all the time and prefer it for managing their email. Gmail's inbox categories, label system, amazing search, and keyboard shortcuts is a pretty tempting concoction of technology.
powerful, even though they didn't reside on the Internet. (I leave Apple Mail running on our family iMac so my mail rules are always working for me.) Additionally, I still had an iCloud account for personal mail and my Microsoft Exchange account for the day job. While those accounts worked fine in Apple Mail, Gmail did not. If I was going to use Gmail, I wanted to get the advantage of all the Gmail technologies, which required me to use it in the web or a Gmail-specific application. So I routinely found that I was going to two different places to manage my email. It was this tedium that ultimately broke my will of staying with Gmail. If I had just one email account, Gmail would have been more compelling.
So I used it exclusively for a while, but ultimately (and surprisingly) I returned to IMAP and Apple Mail as my primary email technology in the end. Using Gmail day-today, I found that I didn't use labels as much as I thought I would. I had the same experience a few years ago with MailTags on the Mac. I am just resistant to taking the time to tag emails because search is so good that I rarely find I miss them. During my Gmail phase, I found that there were some features I missed from Apple Mail, such as VIPs, Automator services, and my Apple mail rules which were more 299
Interestingly, despite all my blathering about privacy in the way that Gmail serves ads, once I started using Gmail, that didn't bother me. Perhaps it's the PRISM disclosures that seem to come out every day, but I just don't assume much email is private anymore.
Having made this world tour of mail applications, I surprised even myself to discover that the best solution for me remains Apple Mail. In addition to the features covered in this book, it also integrates with the operating system like only an application developed by Apple can. It's also scriptable and, overall, gives me a tremendous amount of options and ways for dealing with my email.
Another reason why I ultimately gave up on Gmail was the power of SaneBox. My SaneBox account provides me a lot of the features (particularly inbox filtering) that I liked about Gmail. Indeed, in my experience, SaneBox does a better job of it and adds additional features such as deferred email and reminders. In summary, while I enjoyed my fling with Gmail, I'm perfectly happy with my IMAP accounts moving forward.
MANAGING EMAIL VOLUME The big problem I face is the volume of email I receive. I'm fortunate to have a lot of people writing me. I love hearing from people that read my books or listen to my podcasts and want to share something with me. I love even more when people write me and tell me how something I've done has made their life a little bit better. It is those 300
emails that inspire me to keep giving more and working harder.
And finally I receive a lot of email on my personal account from friends, family, vendors I've dealt with, and all the other bits of email that everyone is all too familiar with.
I also get a lot of emails from people asking me questions about advice over what to buy, what to use, or how to pull off a particular vexing problem. Some of these emails are easy to respond to, and some of them take quite a bit more time. In addition, a lot of people send me emails talking about products they are creating or software they are writing and asking for my opinion about what they are up to. All of these emails are extraordinarily flattering.
So I've got all of these buckets of email coming at me that add up to a large volume of incoming correspondence. In fact, it's just too much for me to manage with the Inbox Zero approach of clearing out the inbox and managing it all with just a few folders. Instead, I use additional inboxes on each account to perform a rough filtering of my emails, which gives me different places with relative priorities for email review and processing.
Then I get email related to my day job. Clients have questions. Opposing counsel will write me concerning the latest bit of litigation, and I receive emails relating to my commitments and professional organizations. 301
Largely, I pull off this trick with SaneBox. I cannot overstate how much I love using this service. It is particularly useful in helping me manage the MacSparky account, where I get the largest volume of email. I have SaneBox watching my MacSparky inbox. Over time, SaneBox has learned where I want my email sorted. If I get an email from Apple or someone I'm working with at Macworld or on one of the books, it leaves it in the inbox.
The MacSparky Account Mailbox List
me, largely automatically. (I am still amazed at how reliable SaneBox is at this seemingly subjective decision.) I also have a SaneBox folder on the MacSparky account called "Later". I have a SaneBox News mailbox on this account where I send emails concerning press releases, new products, and other news-type items related to my MacSparky life.
I have another SaneBox mailbox called "Feedback". Whenever I receive a question or comment from a reader or listener, I always move it from the inbox into that Feedback folder. Over time, SaneBox has figured this out and now does it for
Email that SaneBox doesn't think important enough to leave in the inbox but also doesn't think logically fits in Feedback or News folder goes in the SaneBox Later mailbox. So as I 302
Mailbox Review Frequency
wake up in the morning, I'll have a few items in my inbox, and several more items already sorted in the Later, News, and Feedback mailboxes.
I clear out the Later mailbox once a day. Sometimes clearing out this inbox means simply giving SaneBox more data. For example, there may be feedback-style emails in there that I move to the Feedback mailbox or news-related items that get moved to the News mailbox. I do this using keyboard shortcuts in Apple Mail (the Control+Command+Number trick covered in chapter 4) if I'm doing this on my Mac. Other mail in the Later mailbox that doesn't
I try to tackle each of those mailboxes with their relative level of importance. The inbox always gets managed with an Inbox Zero methodology several times a day. I clear it at least every morning and afternoon. Sometimes I'll hit it more often depending on what I'm doing. 303
fit somewhere else gets handled right then using the Inbox Zero method.
(when Sarah isn't playing with LEGO bricks) specifically for that purpose. Moreover, I don't feel stressed about those emails during the rest of the week because I know they're put in a separate place and that I will have time to go through them later. It takes an hour or two to get through it all, but when I'm done I always feel good about myself not only because I managed to keep up with the feedback email but also because the people who write me are generally really nice and make me feel great. Another improvement in my mental workflow is the ability to file some emails without reply. Not everything needs a reply. The News Mailbox gets reviewed less often. If things get really busy, I may dump a bunch of the news folder without even reading it.
I haven't yet mentioned my Action folder because it is not a SaneBox mailbox, but it does exist and I'll frequently send items from the inbox or Later mailbox to the Action folder. The Action folder always gets managed at least once every couple of days. This is a lot easier because a large volume of email has gone into the feedback and news mailboxes. Once a week I sit down and go through the Feedback folder. Segregating it in this way makes going through the feedback so much more enjoyable. The vast majority of email in that Feedback folder is people just like me and have interesting questions and comments. I don't feel stressed about those emails because I'm doing them at a set time 304
When I first started writing this book, I was pretty hostile to the idea of deferred email. Several email apps in this book, including MailPilot and SaneBox, offer specialized mailboxes that hold email in limbo for a day, a week, or some other set period to get it off your plate in the interim.
deferring email since I'm using it all the time. I could pull this all off manually without SaneBox. I could go through my inbox and sort items manually into Feedback, News, Later, and Action folders. However, I much prefer paying SaneBox to do this for me. Waking up to five items in my inbox instead of 70 makes SaneBox absolutely worth it to me.
In the process of testing this idea for the book, it has grown on me. Now I use three such mailboxes through my SaneBox account: one day, one week, Saturday. Some email gets put into these boxes. I find I use them when I have a non-critical email that will still take some work before responding, and I don't want the emotional weight of seeing it. For me it has become an intermediary step between the Action folder and creating a specific task in OmniFocus to managing the email at some date in the future. I can no longer be critical of
I don’t sort sent email. My MacSparky.com account has a large “sent” mailbox than I can search the same way I search my archive mailbox. For people that instead use project related mailboxes or tags, it would make more sense to tag or save the related sent emails there. I use a similar workflow with my personal email. I have SaneBox automatically sort 305
Later and News mailboxes. The volume isn’t nearly as high on my personal account but separating the news helps a lot. Like the MacSparky account, I clear my inbox every day and my Action folder every few days and my News folder whenever I get around to it.
different buckets of correspondence that I deal with in their relative levels of priority. I use all of the Apple Mail tools covered in this book to get my Mac and iOS devices managing as much of this as possible without requiring my direct involvement. I manage to deal with the truly urgent email on a timely basis and do a pretty good job of dealing with the rest without turning my life upside down every day. Despite the large volume of email I receive, I finally feel like I'm not drowning in it, and that feels pretty good.
For my day-job account, I don't use SaneBox. I manually manage my inbox on that account with the Inbox Zero method. SaneBox gets quite a bit more expensive when you add a third SaneBox email address and I'm still not sure I want anything related to client email going through any other servers. Moreover, the volume is low enough that it is entirely manageable. Pulling all of these technologies together, I've found my peace with email. I have 306
SECTION 2
Serenity Caldwell: Writer
Serenity Caldwell (website) (Twitter) writes about technology for Macworld magazine (website). She also rocks the roller derby circuit for the Boston Derby Dames (website). Serenity deals with a lot of email and has some great tips.
Audio 10.1 Serenity Caldwell Audio Interview
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Rob Corddry: Producer and Actor Rob Corddry is best known as an actor and producer (IMDb) (Twitter). Rob uses Apple technologies to manage an extremely busy schedule and shares his thoughts on email with me. Audio 10.2 Rob Corddry Audio Interview
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Merlin Mann: Writer and Broadcaster Merlin Mann (website) (Twitter) is, in my mind at least, the original productivity blogger. One of the things I love about Merlin is that while he enjoys the nerdy, fiddly parts, he also likes talking about the big picture and underlying problems we face with email.
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Audio 10.3 Merlin Mann Audio Interview
SECTION 5
Fraser Speirs: Educator
Fraser Speirs (webpage)(Twitter) is one of the foremost authorities on using the iPad in education. Fraser is a teacher and geek. He spends a lot of time traveling and sharing his experiences with other educators and has, as a result, an ever-growing inbox. Fraser shares his email workflow.
Audio 10.4 Fraser Speirs Audio Interview
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Jeff Taekman: Physician
Jeff Taekman (website) (Twitter) is an anesthesiologist and academic physician at Duke University. As a doctor and educator, Jeff receives a lot of email and has some great ideas on how to cope.
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Audio 10.5 Jeff Taekman Audio Interview
SECTION 7
Aisha Tyler: Entertainer Aisha Tyler (IMDb)(website) (Twitter) is a well known actress, comedian, writer and emerging director. Aisha is very popular and receives a great deal of email. Aisha was kind enough to share the tools she uses to handle her email while still having time to create things.
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Audio 10.6 Aisha Tyler
Audio Interview
SECTION 8
David Wain: Director and Writer David Wain (IMDb) (website) (Twitter) is a really talented guy. He comes up with ideas, writes a script, directs the movie, and then does the postproduction. Usually, David has several of these projects going on at once. David is also a Gmail power user. In this interview, David shares some great email tips and explains how he uses Gmail.
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Audio 10.7 David Wain
Audio Interview
SECTION 9
Gabe Weatherhead: IT Specialist Gabe Weatherhead (website) (Twitter) is a trained scientist turned IT manager. Gabe is responsible for a large computer network and can’t afford to miss an email. Gabe has spent a lot of time thinking about email and shares some of his wisdom in this interview.
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Audio 10.8 Gabe Weatherhead
Audio Interview
APPENDIX
SECTION 1
Lick a Stamp Now that I’ve shared over 1.1GB worth of data with you about how to get better at email, I’d like to share my deep, dark secret. Once in a while, I like to lick a stamp and send a note the old-fashioned way. There are occasions where an email is not the appropriate medium. When a friend has a new baby, gets that promotion, graduates, or loses a loved one, it makes more sense to send someone a handwritten note. Of course, I have a workflow for that too.
1. GET SOME QUALITY STATIONERY Sending a note on a piece of plain white copy paper is not going to cut it. I’m also not a fan of buying a preprinted greeting card. You are doing something special. Don’t use ordinary materials. Instead, go to a 316
stationery store and buy yourself a nice box set of stationery and matching envelopes. I used storebought paper for years, but recently I’ve started having my own stationery printed by Hoban Press (website). I’m a big fan of Hoban Press and would recommend it, but if that doesn’t work, there are a lot of online stores that sell customized stationery.
If you’d like, you could write these notes on the computer and then use a nice script font to print them, but I just print them nicely. I think there is something special about using your pen instead of a printer, even with dreadful script. Think about the text inside your note before you start writing. Nice stationery is expensive, and you don’t want to waste it. I’ve even been known to write handwritten or iPad-based drafts before putting pen to paper.
2. WRITE YOUR NOTE This is perhaps the hardest part for me, not because I have trouble composing the words but because my handwriting is so terrible. I gave up on handwriting in sixth grade and, thus, have the handwriting of a fifth-grader.
3. GO MEDIEVAL ON YOUR ENVELOPE You aren’t going to be sending these handwritten notes very often so why not 317
make it truly special? Get yourself a wax seal. You can get them online from numerous vendors. I have one with a big S on it and several sticks of sealing wax. Heat your wax over a candle (or match) and drip the wax on the backside of your envelope so that the wax drips on the seam between the envelope lid and paper. Once you’ve got a nice puddle of wax, but before it starts to cool and harden, press your seal into the wax like Richard III, and hold it there for a minute while the wax cools. Lift your seal and you’ve got a note that’s going to make somebody’s day.
Gallery 11.1 Dumping Email for Something More Traditional
As a last touch, I was in the post office and saw they were selling commemorative Miles Davis Stamps. I bought $40 worth and now even my postage reflects me.
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More MacSparky Resources
Mac Power Users Podcast
iTunes
Website
5by5
Episode 164 on Email
Episode 224 on Email
MacSparky.com
Website
Twitter
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Contact and Feedback
FEEDBACK
anyone and not pester you unless I have something really interesting.
Every MacSparky Field Guide gets free updates for at least two years following publication. Have a suggested change? Send me an email.
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SECTION 4
Credits EDITOR Leilani Resurreccion COVER DESIGN Darren Rolfe
Twitter
The Mighty Monocle
AUDIO EDITOR “If you ever find you need help again, you know, if you’re in trouble, need a hand out of a corner ...”
J.F. Brissette
Twitter BETA TEAM J.F. Brissette
“Yeah?” “Please don’t hesitate to get
ILLUSTRATIONS
lost.”
Mike Rohde
Twitter
Website
–Douglas Adams, The Restaurant at the End of the Universe
321
Jean MacDonald
Twitter
Website Eddie Smith
Twitter
Website
IMAGE CREDITS
Archive Boxes - ©depositphotos/toxawww
Chapter 1
Chapter 10
Stack of mail - ©depositphotos/windujedi
Woodworking - ©depositphotos/zigzagmtart
Lego Mac - ©david sparks. I purchased that kit from Chris McVeigh (website).
Microphone - ©depositphotos/alexroz
Chapter 2
Microphone on Audio Interviews - ©depositphotos/ Dragan Jovic
Compass on Map - ©depositphotos/miflippo
Appendix
Chapter 3
Stack of Books - ©depositphotos/nanka-photo
Gears - ©depositphotos/korovin
Chapter 4 MacBook Keyboard - ©depositphotos/CreativeNature
Chapter 8 Vault Door - ©depositphotos/paulfleet Lock and Key - ©depositphotos/fotoall
Chapter 9 322
SECTION 5
Legal Mumbo Jumbo Email, A MacSparky Field Guide, Ver. 1.2
Bulgaria, Canada, Chile, Colombia, Costa Rica, Cyprus, Czech Republic, Denmark, Dominican Republic, Ecuador, El Salvador, Estonia, Finland, France, Germany, Greece, Guatemala, Honduras, Hungary, Ireland, Italy, Latvia, Lithuania, Luxembourg, Malta, Mexico, Netherlands, New Zealand, Nicaragua, Norway, Panama, Paraguay, Peru, Poland, Portugal, Romania, Slovakia, Slovenia, Spain, Sweden, Switzerland, United Kingdom, the United States of America, and Venuzuela.
Lawyers ruin all the fun. Copyright © 2013, 2014 David Sparks Published by David Sparks Foothill Ranch, California Lovingly hand-crafted in the United States of America. ISBN: 978-0-9854561-3-9 Published simultaneously in Argentina, Australia, Austria, Belgium, Bolivia, Brazil, 323
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All trademarks are the property of their respective owners including the following: The terms Apple®, Mac®, iPad®, and iPhone® are registered trademarks of Apple, Inc. For more information on Apple, Inc. and its products, visit www.apple.com. The terms TextExpander® and PDFpen® are registered trademarks of SmileOnMyMac LLC. For more information on Smile products, visit www.smilesoftware.com.
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Other company and product names may be trademarks of their respective owners. MacSparky, The MacSparky Field Guides, and related trade dress are trademarks of David Sparks, and may not be used without written permission. 324
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Of course the lawyer had to add this. The publisher and the author make no representations or warranties with respect to the accuracy or completeness of the contents of this work and specifically disclaim all warranties, including without limitation warranties of fitness for a particular purpose. No warranty may be created or extended by sales or promotional materials. The advice and strategies contained herein may not be suitable for every situation. This work is sold with the understanding that the publisher is not engaged in rendering legal, accounting, or other professional services. If professional assistance is required, the services of a competent professional person should be sought. Neither the publisher nor the author 325
