Email, Still A Sonofabitch

Posted: May 12, 2013 in Column, GT, Technology

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.

  1. There’s definately a great deal to learn about this topic. I love all the points you’ve made.

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