Email, Still A Sonofabitch

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Just about two years ago, I went off the deep end. I had come home early from an event in an effort to do something responsible: email. I was on the road and knew the situation would be dire (since I had not been checking my email all day). I was wrong. It was a disaster. It may as well have been Inbox Trillion. There was no way I could get through it all with my sanity intact. So I did the only logical thing. I quit email.

It was both an experiment and a statement. I decided that I wasn’t going to respond to email for an entire month. And while I did cheat a little (I would still check it from time-to-time in case of emergencies and to delegate some work-related items that couldn’t wait), it was without question one of the best months I’ve ever had.

I was decidedly less stressed out. I found myself enjoying the internet more. I no longer dreaded opening up my laptop or looking at the push notifications on my phone. And guess what? If someone really needed to talk with me about something, they figured out a way. Funny how that works.

And yet, the good times couldn’t last. The month came to a close and I was back on email. While I don’t think I actually missed anything in my time away, the sheer ubiquity of the medium and the realities of life brought email back into my life full time.

And I hate it more than ever.

In the months and now years following the experiment, a number of people have asked for an update on my epic battle with email. The good news is that a few things have gotten much better. The bad new is that everything else has gotten much worse.

After my experiment, I tried a bunch of different things to make my email situation more tenable. What I ended up coming to was a system where I would be checking email constantly throughout a day, responding to what I could quickly from my phone, archiving anything that didn’t need a response, and keeping the rest in my inbox until late at night, when the incoming volume would drop to near zero. Anything that wasn’t timely would then sit in my inbox until the weekend when the incoming volume is uniformly lower.

It was a bit like letting pressure build up (quite literally, you might say) and releasing a bit of it at night so my inbox wouldn’t explode. And then releasing the rest of it every weekend. And then starting over on Monday. Every Monday. Forever.

This was my life. And while it was manageable, you know what? It still sucked. Because I would find myself getting gradually more and more stressed out throughout the week as I saw my inbox grow and grow leading up to the weekend release. It made me more stressed out on Friday than on Monday. I now somewhat dreaded the weekend. Email time.

Then one day a CrunchFund portfolio company asked to run an idea by me. That company, Orchestra, was planning to take what they had learned from their to-do list app and make a new kind of email client. That, of course, became Mailbox.

From the moment I first heard the idea, I knew it was a winner. It was essentially taking a lot of what I was manually doing with email and streamlining the process. And they were doing it in an extremely smart and even sort of fun way, using the native niceties of modern smartphones.

Mailbox quickly became my most-used app. It still is. It basically alleviates the pressure build-up in my inbox by allowing me to release it constantly throughout a day. Brilliant.

But also sort of an illusion.

I’m not alleviating the pressure by responding to emails right away. Instead, I’m pushing them off to deal with at a later time. My system of responding to emails at night or on the weekend is largely the same, I simply no longer have to watch those emails build up until I am ready to take action.

Now, don’t underestimate how wonderful such a system is. And it’s a system that will continue to improve with automations and the like now that Mailbox has the resources of Dropbox behind them. But don’t be fooled into thinking that the problems of email have been solved. The underlying issues very much remain.

Mailbox simply perfected the game of Whac-A-Mole that we all play.

One major issue that remains with email is the notion that every message should get a response. And a big reason why I hate responding to email during the day is that too many people are too quick to respond to my reponses. For every email I send in the day, I seem to get two in return — often immediately. (As a result, this caged animal has been learning not to touch the electric fence — hence, night and weekend emailing.) And a large number of those responses are “K” or “Cool” or “Great” or “Thx” or some other banality best left unemailed.

The problem with these responses, even the short ones, is that they all take time to consume. If I read them in Gmail, it takes a couple seconds to load the response. And then another couple seconds to archive it. If I read them on my phone, I have to wait a few more seconds to download the messages from the server. Not to mention the push notifications that come in alerting you to the new message, taking up yet more precious seconds.

Seconds make up minutes, which make up hours, which make up days, which make up months, which make up years. One day we’ll all be laying on our death beds wishing we hadn’t wasted all that time reading a million “K” email responses in our lives.

Email needs some sort of quick response or maybe even a no-response reply system. Maybe it’s read/unread states that all recipients can see. But that’s been tried before and understandably, some people don’t like others to know when they’ve read a message. So maybe it needs to be a simple checkmark, like Path recently introduced in its new messaging system.

Or maybe the answer is something like emoji/smilies/stickers. Believe me, I know how lame this must sound. I mean, stickers for Chrissakes?! But ignore the immense cuteness and joy of stickers for a second and focus on what they signify: an ultra-quick way to express a reaction. This could work for email too.

Neither of these things would work if they simply came in the form of yet another email response — thus, defeating the purpose. Rather, these should be in the form of some sort of quick-loading visual cue that resides *on top* of an email system. That would likely require everyone using the same email service (unless this somehow became a new standard that every email service provider adopted — not gonna happen). But perhaps a fall-back system could be put in place to deliver these quick messages in email form if the recipient isn’t using the correct email service (giving them an incentive to sign up).

I guess my point is that while we’re seeing a lot of services come out with new and interesting ways to combat email overload — beyond Mailbox, see: Handle, Triage, Evomail, Mail Pilot, and many others — the only way email ever truly gets “fixed” is to be completely re-imagined. It doesn’t need a paint job, it needs a demolition job.

My fear is that this will never happen. We’ll keep getting better tools to handle email on various devices (on your iPhone, on your iPad, on your iWatch, on Google Glass, etc) but eventually the moles will become too quick and plentiful for any of us to whack.

At that point, email will become something we only use for work while we use some other quick messaging system for everything else. This is already happening to some extent — when was the last time you sent an email for “fun”? — but the messaging world is increasingly fragmented and not universal.

Earlier this week, I announced my next step professionally. It resulted in over a hundred emails of well-wishes and congratulations. These should have left me feeling wonderful. They did not. Unfortunately, the medium has become the message.

[Disclosure: It would probably be easier for me to list where I *don’t* have some sort of conflict in the things mentioned above — see here. The one thing I’m not conflicted about: how much I hate email.]