Deciphering Glyph :: Email Isn’t The Thing You’re Bad At

I’ve been using the Internet for a good 25 years now, and I’ve been lucky enough to have some perspective dating back farther than that. The common refrain for my entire tenure here:

We all get too much email.

A New, New, New, New Hope

Luckily, something is always on the cusp of replacing email. AOL instant messenger will totally replace it. Then it was blogging. RSS. MySpace. Then it was FriendFeed. Then Twitter. Then Facebook.

Today, it’s in vogue to talk about how Slack is going to replace email. As someone who has seen this play out a dozen times now, let me give you a little spoiler:

Slack is not going to replace email.

But Slack isn’t the problem here, either. It’s just another communication tool.

The problem of email overload is both ancient and persistent. If the problem were really with “email”, then, presumably, one of the nine million email apps that dot the app-stores like mushrooms sprouting from a globe-spanning mycelium would have just solved it by now, and we could all move on with our lives. Instead, it is permanently in vogue¹ to talk about how overloaded we all are.

If not email, then what?

If you have twenty-four thousand unread emails in your Inbox, like some kind of goddamn animal, what you’re bad at is not email, it’s transactional interactions.

Different communication media have different characteristics, but the defining characteristic of email is that it is the primary mode of communication that we use, both professionally and personally, when we are asking someone else to perform a task.

Of course you might use any form of communication to communicate tasks to another person. But other forms - especially the currently popular real-time methods - appear as a bi-directional communication, and are largely immutable. Email’s distinguishing characteristic is that it is discrete; each message is its own entity with its own ID. Emails may also be annotated, whether with flags, replied-to markers, labels, placement in folders, archiving, or deleting. Contrast this with a group chat in IRC, iMessage, or Slack, where the log is mostly² unchangeable, and the only available annotation is “did your scrollbar ever move down past this point”; each individual message has only one bit of associated information. Unless you have catlike reflexes and an unbelievably obsessive-compulsive personality, it is highly unlikely that you will carefully set the “read” flag on each and every message in an extended conversation.

All this makes email much more suitable for communicating a task, because the recipient can file it according to their system for tracking tasks, come back to it later, and generally treat the message itself as an artifact. By contrast if I were to just walk up to you on the street and say “hey can you do this for me”, you will almost certainly just forget.

The word “task” might seem heavy-weight for some of the things that email is used for, but tasks come in all sizes. One task might be “click this link to confirm your sign-up on this website”. Another might be “choose a time to get together for coffee”. Or “please pass along my resume to your hiring department”. Yet another might be “send me the final draft of the Henderson report”.

Email is also used for conveying information: here are the minutes from that meeting we were just in. Here is transcription of the whiteboard from that design session. Here are some photos from our family vacation. But even in these cases, a task is implied: read these minutes and see if they’re accurate; inspect this diagram and use it to inform your design; look at these photos and just enjoy them.

So here’s the thing that you’re bad at, which is why none of the fifty different email apps you’ve bought for your phone have fixed the problem: when you get these messages, you aren’t making a conscious decision about:

1. how important the message is to you
2. whether you want to act on them at all
3. when you want to act on them
4. what exact action you want to take
5. what the consequences of taking or not taking that action will be

This means that when someone asks you to do a thing, you probably aren’t going to do it. You’re going to pretend to commit to it, and then you’re going to flake out when push comes to shove. You’re going to keep context-switching until all the deadlines have passed.

In other words:

The thing you are bad at is saying ‘no’ to people.

Sometimes it’s not obvious that what you’re doing is saying ‘no’. For many of us — and I certainly fall into this category — a lot of the messages we get are vaguely informational. They’re from random project mailing lists, perhaps they’re discussions between other people, and it’s unclear what we should do about them (or if we should do anything at all). We hang on to them (piling up in our Inboxes) because they might be relevant in the future. I am not advocating that you have to reply to every dumb mailing list email with a 5-part action plan and a Scrum meeting invite: that would be a disaster. You don’t have time for that. You really shouldn’t have time for that.

The trick about getting to Inbox Zero³ is not in somehow becoming an email-reading machine, but in realizing that most email is worthless, and that’s OK. If you’re not going to do anything with it, just archive it and forget about it. If you’re subscribed to a mailing list where only 1 out of 1000 messages actually represents something you should do about it, archive all the rest after only answering the question “is this the one I should do something about?”. You can answer that question after just glancing at the subject; there are times when checking my email I will be hitting “archive” with a 1-second frequency. If you are on a list where zero messages are ever interesting enough to read in their entirety or do anything about, then of course you should unsubscribe.

Once you’ve dug yourself into a hole with thousands of “I don’t know what I should do with this” messages, it’s time to declare email bankruptcy. If you have 24,000 messages in your Inbox, let me be real with you: you are never, ever going to answer all those messages. You do not need a smartwatch to tell you exactly how many messages you are never going to reply to.

We’re In This Together, Me Especially

A lot of guidance about what to do with your email addresses email overload as a personal problem. Over the years of developing my tips and tricks for dealing with it, I certainly saw it that way. But lately, I’m starting to see that it has pernicious social effects.

If you have 24,000 messages in your Inbox, that means you aren’t keeping track or setting priorities on which tasks you want to complete. But just because you’re not setting those priorities, that doesn’t mean nobody is. It means you are letting availability heuristic - whatever is “latest and loudest” - govern access to your attention, and therefore your time. By doing this, you are rewarding people (or #brands) who contact you repeatedly, over inappropriate channels, and generally try to flood your attention with their priorities instead of your own. This, in turn, creates a culture where it is considered reasonable and appropriate to assume that you need to do that in order to get someone’s attention.

Since we live in the era of subtext and implication, I should explicitly say that I’m not describing any specific work environment or community. I used to have an email startup, and so I thought about this stuff very heavily for almost a decade. I have seen email habits at dozens of companies, and I help people in the open source community with their email on a regular basis. So I’m not throwing shade: almost everybody is terrible at this.

And that is the one way that email, in the sense of the tools and programs we use to process it, is at fault: technology has made it easier and easier to ask people to do more and more things, without giving us better tools or training to deal with the increasingly huge array of demands on our time. It’s easier than ever to say “hey could you do this for me” and harder than ever to just say “no, too busy”.

Mostly, though, I want you to know that this isn’t just about you any more. It’s about someone much more important than you: me. I’m tired of sending reply after reply to people asking to “just circle back” or asking if I’ve seen their email. Yes, I’ve seen your email. I have a long backlog of tasks, and, like anyone, I have trouble managing them and getting them all done⁴, and I frequently have to decide that certain things are just not important enough to do. Sometimes it takes me a couple of weeks to get to a message. Sometimes I never do. But, it’s impossible to be mad at somebody for “just checking in” for the fourth time when this is probably the only possible way they ever manage to get anyone else to do anything.

I don’t want to end on a downer here, though. And I don’t have a book to sell you which will solve all your productivity problems. I know that if I lay out some incredibly elaborate system all at once, it’ll seem overwhelming. I know that if I point you at some amazing gadget that helps you keep track of what you want to do, you’ll either balk at the price or get lost fiddling with all its knobs and buttons and not getting a lot of benefit out of it. So if I’m describing a problem that you have here, here’s what I want you to do.

Step zero is setting aside some time. This will probably take you a few hours, but trust me; they will be well-spent.

Email Bankruptcy

First, you need to declare email bankruptcy. Select every message in your Inbox older than 2 weeks. Archive them all, right now. In the past, you might have to worry about deleting those messages, but modern email systems pretty much universally have more storage than you’ll ever need. So rest assured that if you actually need to do anything with these messages, they’ll all be in your archive. But anything in your Inbox right now older than a couple of weeks is just never going to get dealt with, and it’s time to accept that fact. Again, this part of the process is not about making a decision yet, it’s just about accepting a reality.

Mailbox Three

One extra tweak I would suggest here is to get rid of all of your email folders and filters. It seems like many folks with big email problems have tried to address this by ever-finer-grained classification of messages, ever more byzantine email rules. At least, it’s common for me, when looking over someone’s shoulder to see 24,000 messages, it’s common to also see 50 folders. Probably these aren’t helping you very much.

In older email systems, it was necessary to construct elaborate header-based filtering systems so that you can later identify those messages in certain specific ways, like “message X went to this mailing list”. However, this was an incomplete hack, a workaround for a missing feature. Almost all modern email clients (and if yours doesn’t do this, switch) allow you to locate messages like this via search.

Your mail system ought to have 3 folders:

1. Inbox, which you process to discover tasks,
2. Drafts, which you use to save progress on replies, and
3. Archive, the folder which you access only by searching for information you need when performing a task.

Getting rid of unnecessary folders and queries and filter rules will remove things that you can fiddle with.

Moving individual units of trash between different heaps of trash is not being productive, and by removing all the different folders you can shuffle your messages into before actually acting upon them you will make better use of your time spent looking at your email client.

There’s one exception to this rule, which is filters that do nothing but cause a message to skip your Inbox and go straight to the archive. The reason that this type of filter is different is that there are certain sources or patterns of message which are not actionable, but rather, a useful source of reference material that is only available as a stream of emails. Messages like that should, indeed, not show up in your Inbox. But, there’s no reason to file them into a specific folder or set of folders; you can always find them with a search.

Make A Place For Tasks

Next, you need to get a task list. Your email is not a task list; tasks are things that you decided you’re going to do, not things that other people have asked you to do⁵. Critically, you are going to need to parse e-mails into tasks. To explain why, let’s have a little arithmetic aside.

Let’s say it only takes you 45 seconds to go from reading a message to deciding what it really means you should do; so, it only takes 20 seconds to go from looking at the message to remembering what you need to do about it. This means that by the time you get to 180 un-processed messages that you need to do something about in your Inbox, you’ll be spending an hour a day doing nothing but remembering what those messages mean, before you do anything related to actually living your life, even including checking for new messages.

What should you use for the task list? On some level, this doesn’t really matter. It only needs one really important property: you need to trust that if you put something onto it, you’ll see it at the appropriate time. How exactly that works depends heavily on your own personal relationship with your computers and devices; it might just be a physical piece of paper. But for most of us living in a multi-device world, something that synchronizes to some kind of cloud service is important, so Wunderlist or Remember the Milk are good places to start, with free accounts.

Turn Messages Into Tasks

The next step - and this is really the first day of the rest of your life - start at the oldest message in your Inbox, and work forward in time. Look at only one message at a time. Decide whether this message is a meaningful task that you should accomplish.

If you decide a message represents a task, then make a new task on your task list. Decide what the task actually is, and describe it in words; don’t create tasks like “answer this message”. Why do you need to answer it? Do you need to gather any information first?

If you need to access information from the message in order to accomplish the task, then be sure to note in your task how to get back to the email. Depending on what your mail client is, it may be easier or harder to do this⁶, but in the worst case, following the guidelines above about eliminating unnecessary folders and filing in your email client, just put a hint into your task list about how to search for the message in question unambiguously.

Once you’ve done that:

Archive the message immediately.

The record that you need to do something about the message now lives in your task list, not your email client. You’ve processed it, and so it should no longer remain in your inbox.

If you decide a message doesn’t represent a task, then:

Archive the message immediately.

Do not move on to the next message until you have archived this message. Do not look ahead⁷. The presence of a message in your Inbox means you need to make a decision about it. Follow the touch-move rule with your email. If you skip over messages habitually and decide you’ll “just get back to it in a minute”, that minute will turn into 4 months and you’ll be right back where you were before.

Circling back to the subject of this post; once again, this isn’t really specific to email. You should follow roughly the same workflow when someone asks you to do a task in a meeting, or in Slack, or on your Discourse board, or wherever, if you think that the task is actually important enough to do. Note the slack timestamp and a snippet of the message so you can search for it again, if there is a relevant attachment. The thing that makes email different is really just the presence of an email box.

Banish The Blue Dot

Almost all email clients have a way of tracking “unread” messages; they cheerfully display counters of them. Ignore this information; it is useless. Messages have two states: in your inbox (unprocessed) and in your archive (processed). “Read” vs. “Unread” can be, at best, of minimal utility when resuming an interrupted scanning session. But, you are always only ever looking at the oldest message first, right? So none of the messages below it should be unread anyway...

Be Ruthless

As you try to start translating your flood of inbound communications into an actionable set of tasks you can actually accomplish, you are going to notice that your task list is going to grow and grow just as your Inbox was before. This is the hardest step:

Decide you are not going to do those tasks, and simply delete them. Sometimes, a task’s entire life-cycle is to be created from an email, exist for ten minutes, and then have you come back to look at it and then delete it. This might feel pointless, but in going through that process, you are learning something extremely valuable: you are learning what sorts of things are not actually important enough to do you do.

If every single message you get from some automated system provokes this kind of reaction, that will give you a clue that said system is wasting your time, and just making you feel anxious about work you’re never really going to get to, which can then lead to you un-subscribing or filtering messages from that system.

Tasks Before Messages

To thine own self, not thy Inbox, be true.

Try to start your day by looking at the things you’ve consciously decided to do. Don’t look at your email, don’t look at Slack; look at your calendar, and look at your task list.

One of those tasks, probably, is a daily reminder to “check your email”, but that reminder is there more to remind you to only do it once than to prevent you from forgetting.

I say “try” because this part is always going to be a challenge; while I mentioned earlier that you don’t want to unthinkingly give in to availability heuristic, you also have to acknowledge that the reason it’s called a “cognitive bias” is because it’s part of human cognition. There will always be a constant anxious temptation to just check for new stuff; for those of us who have a predisposition towards excessive scanning behavior have it more than others.

Why Email?

We all need to make commitments in our daily lives. We need to do things for other people. And when we make a commitment, we want to be telling the truth. I want you to try to do all these things so you can be better at that. It’s impossible to truthfully make a commitment to spend some time to perform some task in the future if, realistically, you know that all your time in the future will be consumed by whatever the top 3 highest-priority angry voicemails you have on that day are.

Email is a challenging social problem, but I am tired of email, especially the user interface of email applications, getting the blame for what is, at its heart, a problem of interpersonal relations. It’s like noticing that you get a lot of bills through the mail, and then blaming the state of your finances on the colors of the paint in your apartment building’s mail room. Of course, the UI of an email app can encourage good or bad habits, but Gmail gave us a prominent “Archive” button a decade ago, and we still have all the same terrible habits that were plaguing Outlook users in the 90s.

Of course, there’s a lot more to “productivity” than just making a list of the things you’re going to do. Some tools can really help you manage that list a lot better. But all they can help you to do is to stop working on the wrong things, and start working on the right ones. Actually being more productive, in the sense of getting more units of work out of a day, is something you get from keeping yourself healthy, happy, and well-rested, not from an email filing system.

You can’t violate causality to put more hours into the day, and as a frail and finite human being, there’s only so much work you can reasonably squeeze in before you die.

The reason I care a lot about salvaging email specifically is that it remains the best medium for communication that allows you to be in control of your own time, and by extension, the best medium for allowing people to do creative work.

Asking someone to do something via SMS doesn’t scale; if you have hundreds of unread texts there’s no way to put them in order, no way to classify them as “finished” and “not finished”, so you need to keep it to the number of things you can fit in short term memory. Not to mention the fact that text messaging is almost by definition an interruption - by default, it causes a device in someone’s pocket to buzz. Asking someone to do something in group chat, such as IRC or Slack, is similarly time-dependent; if they are around, it becomes an interruption, and if they’re not around, you have to keep asking and asking over and over again, which makes it really inefficient for the asker (or the asker can use a @highlight, and assume that Slack will send the recipient, guess what, an email).

Social media often comes up as another possible replacement for email, but its sort order is even worse than “only the most recent and most frequently repeated”. Messages are instead sorted by value to advertisers or likeliness to increase ‘engagement’”, i.e. most likely to keep you looking at this social media site rather than doing any real work.

For those of us who require long stretches of uninterrupted time to produce something good – “creatives”, or whatever today’s awkward buzzword for intersection of writers, programmers, graphic designers, illustrators, and so on, is – we need an inbound task queue that we can have some level of control over. Something that we can check at a time of our choosing, something that we can apply filtering to in order to protect access to our attention, something that maintains the chain of request/reply for reference when we have to pick up a thread we’ve had to let go of for a while. Some way to be in touch with our customers, our users, and our fans, without being constantly interrupted. Because if we don’t give those who need to communicate with such a tool, they’ll just blast @everyone messages into our slack channels and @mentions onto Twitter and texting us Hey, got a minute? until we have to quit everything to try and get some work done.

Questions about this post?

Go ahead and send me an email.

Acknowledgements

As always, any errors or bad ideas are certainly my own.

First of all, Merlin Mann, whose writing and podcasting were the inspiration, direct or indirect, for many of my thoughts on this subject; and who sets a good example because he won’t answer your email.

Thanks also to David Reid for introducing me to Merlin's work, as well as Alex Gaynor, Tristan Seligmann, Donald Stufft, Cory Benfield, Piët Delport, Amber Brown, and Ashwini Oruganti for feedback on drafts.