Zach Simmons On Why Email Leads to Frustration

If you’re like most people who spend their days at the computer, those days probably have a lot to do with email.

Email has become the glue that ties our workdays together. We can communicate with pretty much anyone, anywhere, anytime. Interactions that used to require scheduling a face-to-face meeting or a phone call can be handled asynchronously. All things considered, it’s a pretty amazing tool. But, that ease of communication can create a deluge that can drag down your entire day if you’re not careful.

In the average 5-day work week, about a day and a half of it is spent on email.

That’s right. Email takes up around 28% of the average desk-worker’s day. This has been borne out in several studies, and we’ve seen similar numbers across our user base. That’s just shy of two and a half hours in an eight-hour day (or 11.2 hours per week). It may seem like a lot, but even that number doesn’t tell the whole story.

That’s because email has evolved into something it was never supposed to be—an endless mishmash of notifications, poorly organized into a tangled hierarchy of folders and labels and an overflow of fragmented, rigid conversations. Email has, thereby, drifted farther away from its primary purpose: to help people communicate.

To prescribe how to make email modern, we need to fully understand how it lost its way.

Which brings us to the weird love-hate dynamic everyone seems to have with email. We’ve let it seep into every nook and cranny of our lives, and we resent its presence. But we also crave it. I asked psychologist Larry Rosen, who specializes in studying our evolving mental relationship with technology: What the hell is up with this?

“Email has become an approach/avoid conflict for us,” Rosen says. “We know there might be a gem in [our inbox] somewhere right now, but we have to sift through all the crap to find it.” Rosen explains that the accessibility of email and its unpredictable pleasures stimulate our brain’s “seeking” circuits. These circuits are mediated by the neurotransmitter dopamine, which helps the brain assign salience and incentive to stimuli, depending on an evaluation of likely reward.

In other words, we may despise our inboxes (and 99% of what’s in them), but we’re neurochemically compelled to make sure that there isn’t something potentially important or pleasurable lurking in there this time—and the evaluation of the uncertainty is what draws us in every time, so that five minutes from now, and then again, and again, we check for the unknown. “The internal stimulus is the one that gets you,” Rosen says. “On balance, [email is] maybe 10% pleasure and 90% fear of missing out.”

But we’ve moved on since then. Other communication media provide us with either better clarity on the importance of a message, or are more focused on a particular type of content that fits a specific context of use. If design isn’t about solutions as much as it is, as Charles Eames said, “an expression of purpose… a method of action,” then perhaps the question any designer interested in email should ask is not “What can we do about it?” but rather: “What will I do with (or without) it?”

Mission Creep

Most email is work-related, owing to its ARPANET origins and memorandum-like format. But email has too many jobs: project management, to-do lists, group discussions, file transfer, document editing—it’s endless. “Email is so generic, it’s not specialized,” Asana’s Justin Rosenstein (inventor of the Like button, among others) says. “We’re using email for things that it intrinsically sucks at.”

Apps like Asana and Wrike on one hand, and HipChat and Slack on the other, aim to lighten your inbox by offloading as many “things email sucks at” as possible. Asana and Wrike replace team status-tracking and project management messages. HipChat and Slack replace interoffice mail and group message threads; the goal is to “box in” email to the tasks only it (and not some nimbler, newer tech) can do well. That basically means any kind of external communication, which is still a lot.

“I spend four or five hours a day on email,” admits Slack’s Butterfield. “Its virtue is that it crosses organizational boundaries, it’s the lowest common denominator, it’s the lingua franca of computer-mediated communication. It’s how we set up this conversation.”

Here’s what makes email the most reviled technology ever, Stewart Butterfield says: “There’s a billion freaking things you have to do in your life, and email is the distillation of the other stuff that other people want you to do.” So maybe the solution to email is just what Paul Ford said: taking, if not full control of our lives, then at least fuller responsibility for them. Passing the buck is a toxic behavior at work, and, not coincidentally, is something that email is great at enabling.

In short, we’ve got other ways to communicate, more effective ways to communicate. Email’s seen its day and I dare say it’s time for it to die. As if the toxic psychology of interaction, alongside the lack of focus, didn’t give us enough reasons to hate email, here are five more:

Reason 1. A Time Vampire

Modern attempts to deal with email head-on don’t try to boil the ocean of incoming messages. Instead, they accept it as a given, and instead try to assist or automate our hapless, dopamine-driven efforts to “process” it. Gmail Inbox and the now-deceased Mailbox take this stance. With quick gestures, snooze buttons, and smart labels, they try to reduce the cognitive load of sorting the email wheat from the chaff. The trouble, Rosen says, is that “the triage is a never-ending process. You have to constantly attend to it, or just let your email pile up and say, ‘Eh, if i miss something here and it’s important, they’ll get in touch with me some other way.’”

Reason 2: Ugly

It’s pretty damn ugly. For technical reasons, the content of an email is but a shadow of the experience we’ve come to expect from the web. Even when desktop email clients like Apple Mail do their best to make it look pretty, there’s not much that can be done for the way messages are “threaded:” obnoxious indenting and chevron (>>>>>) characters occur throughout them, and heaven help you if someone decides to respond inline because it will shatter all continuity.

Reason 3: The Problem of Search

Searching emails takes longer than searching almost anything else because of the way emails are “stored.” They’re badly indexed and the same kinds of search improvements that are making the web and other media for communication more useful are mostly absent from email.

Reason 4: Emails are Easy to Fake

Emails are so easy to forge, even to the average user who’s not generally interested in a career in forgery. Sending an email from an address that isn’t yours is easy as pie and believable, too. It’s a great way to start a dispute between two ignorant victims (in some cases, this is good when following the classic “divide and conquer” strategy).

Reason 5: Forwards, Spam, and other Abuses and Usurpations of Your Email Address

If you’ve had your email address for more than a year then you’re well aware of this problem. You know, chain-mail? Yeah. Hated those. And I still get them, too; emails telling me to forward this or I’ll die, emails telling me of Obama’s conspiracy to make America a Muslim country, even emails telling me to forward the email or Mickey Mouse will kill me at midnight. Emails telling me that despite what my wife thinks, I could use a little help…you know. Scary stuff. And laughable. Always laughable, but mostly annoying.

Thankfully, some providers like Gmail have stepped in with filters to try and stop the problem, but they don’t always succeed and Gmail is by a long shot the best at what it does (as in, I still get a lot of Spam in my Inbox on other providers, despite their filters).


Email was never meant to be a tangle of folders and labels. It was meant for talking. All folders and labels have done is tee up the strongest communication platform we have to become a disjointed to-do list that slugs work along at a snail’s pace. As this jumbled, inefficient framework hosts bits and pieces of different projects, asks and tasks in different places, meaningful human conversation is slipping away with each stodgy, minimum-commitment note.

Once upon a time, getting an email was exciting. The icon for a tiny red flag would pop up, and your eyes would light up. In the 1990s, Tom Hanks and Meg Ryan were even in a Nora Ephron movie that lionized the power and charm of email. Today, though, email’s glory days are over, and it has become the most headache-inducing, inefficient technology we use daily. We are the mobile messaging, snapchatting generation, and it’s time email joined us.

We don’t need to tame this existing system, though, we need a completely new one. Email apps thus far have just worked within this the overflowed, tangled system that email is now to make the to-do lists marginally more swift and manageable. It’s like a painkiller, a quick relief that neglects fixing the actual problem.

We’re on the hinge of a paradigm shift that isn’t about taming email, not about beating it to death, but rather unlocking a newfound potential so it can finally flourish again. We may despise our inboxes, but we’re neurochemically compelled to make sure that there is no potentially important thing lurking in there.

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