It’s Your Fault Email Is Broken

As an email startup CEO, I hear it every week. “I hate email. Email sucks. Why can’t anyone fix it? And why would you want to spend your life working on something everyone hates?”

Email is an obvious target for blame, since we collectively send 183 billion of them every single day. But blaming email is like shooting the messenger (or shooting the envelope, rather).

Email is a protocol. It is an elegant, useful, even beautiful medium. Because so much of our work and so many of our decisions come in via email however, it’s easy to attribute to email itself the difficulties of dealing with that work and making those decisions. It’s equally easy to try to replace or fix email in ways that actually amplify the real problems we face.

Over the past few years, there has been a ton of activity in the messaging space. Unfortunately, most of the new thinking and products fall into two buckets, neither of which address the fundamental problems that are really plaguing us when we complain about our email.

Replace Email With Something Real-Time

The only thing that gets more attention in Silicon Valley than a huge venture round is a pronouncement that somebody is going to kill email with a new real-time communication protocol.

Facebook is on their third generation of plans to kill email. Mobile messaging has been going to kill email for the past four years. This year, Slack is going to kill email. Asana might still be going to kill email. Maybe the thing that saves Twitter’s stock price will be killing email.

Beyond the drawbacks of sending our critical communication into closed, proprietary systems, there are serious behavioral and etiquette problems that arise when replacing an asynchronous communication channel like email with a synchronous one like chat or instant messaging.

First, real-time communication tools are even more addictive than email. Because conversations that would take 3-4 emails instead show up as 20-35 chat exchanges, our brains get a dopamine hit 20-35 times instead of 3-4.

Research shows that these dopamine hits are addictive — and that we lose focus every time one of them arrives.

Second, these tools create the expectation that responses will be instant, creating social pressure to always make responding to messages our top priority. That prevents us from focusing on the work that matters most — work that requires deeper thought or deliberation.

We end up spending our days just chatting with each other, or doing urgent things instead of important ones.

Finally, the meandering nature of real-time conversations makes it difficult to catch up quickly after leaving the stream to work on something important. Because there’s no way to scan through a chat conversation to see what’s important or relevant other than reading every message on every channel, real-time tools create a barrier to doing focused work.

While not always perfect, email subject lines and topic-based organization at least provide a general guidepost when reviewing discussions after the conversation has concluded. Subject lines also make it much easier to find information months or years after a conversation has ended — I’m not at all looking forward to finding the history around a decision in my chat logs five years from now.

The addictive nature of real-time tools, coupled with the difficulty of staying organized if you leave the stream, creates a perfect storm for companies peddling productivity but profiting from increasing stress and decreasing focus. These tools may feel good to use, but they’re amplifying the problems we attribute to email rather than reducing their impact.

I’d even argue that one can predict the success of a fledgling company based on their ratio of synchronous to asynchronous digital communication. The more a team is able to focus on real priorities, the more likely they are to create something of value rather than just talking about it.

Build Yet-Another-Email-Triage-Tool

The other main communications innovation approach is to build better tools to help us triage our email.

From Gmail, we’ve seen Priority Inbox, Tabs and now Bundles. Each attempts to automatically sort messages into stuff that matters and stuff that doesn’t. From Microsoft, we’ve seen Sweep and now Focused Inbox, two approaches to solving the same problem. And there are many others too: OtherInbox,, and a slew of mobile mail clients like Mailbox that try to make it faster to triage email via gestures.

I’m all for adding great tools to email. Heck, I’ve spent the last five years building them! Boomerang is part of a constellation of apps and services that enhance, extend and/or reimagine email for modern contexts.

We’ve done the math. It takes the average email user about 5 minutes to delete all of the marketing messages we don’t care about each day, without any of these tools. Using any one of them, it takes about three minutes to go through the pile.

Sure, we may be able to reduce that 3 minutes to 2.5 with a slightly better algorithm or another UI technique. But we need to be thinking about something else: the remaining 1 hour and 57 minutes we spend in our email every day to really make progress. Moving to chat doubles that number to nearly 4 hours, by the way.

So where do we go from here?

It takes courage to admit it, but the real problem with email isn’t with email at all. It’s with human nature, and with the nature of knowledge work.

In a recent study by Kostadin Kushlev and Elizabeth W. Dunn, they found that over 81 percent of U.S. employees respond to emails within an hour (32 percent within 15 minutes). What’s even more surprising, though, is that 6 percent of respondents checked their email while they or their spouses were in labor. That’s not email — that’s us.

We have too much work to do. We have too many decisions to make. We have too many people legitimately asking for our attention every day.

It doesn’t matter whether that work, those decisions, and those requests for our attention come into our email inboxes, our text message inboxes, our Facebook inboxes, or as a new line in our chat clients. It’s all the same. Adding a new triage tool or routing more communication into real-time channels doesn’t make any of that work go away.

The reason we keep making incrementally minded new tools is because we are afraid to look in the mirror knowing that, consciously or not, what we’ll see may not be pretty. It is so much easier to connect a new add-on to your Gmail than it is to commit to changing your human operating system.

Shutting your laptop, putting your phone on the table, reinitiating eye contact during meetings, turning off notifications, drafting messages in a non-email substrate, and managing by walking around instead of by repurposing subject lines as text messages are a few easy ways to get started making a deeper change.

Our product philosophy has always been driven by the idea that behind any communications channel are real people trying to get real work done. We need to be thinking about how we can help those people focus on what’s most important and what’s most impactful. That doesn’t change whether we’re communicating face-to-face, via telegraph, via phone, via text, via chat, via email, or via the direct brain-to-brain link that we’ll use in the future.