Why email sucks and what we can do about it

By Erez Pilosof , written on August 27, 2013

From The News Desk

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.

That’s because email has evolved into something it was never supposed to be – an endless mishmash of notifications poorly organized into riddled folders and labels and an overflow of fragmented, rigid conversations. In turn, email has drifted further away from its primary purpose: to help people communicate. We need to put human conversation back at the center of the experience, if email is ever going to function properly. That doesn’t mean reverting to the format from the days of the red flag icon, though. It means we are the mobile messaging, snapchatting generation, and it’s time email joined us.

To prescribe how to make email modern, we need to fully understand how it lost its way. The transformation can be broken into four stages:

1. Before the Common Internet (BCI)

Contrary to popular belief there was life online before the Web. The BBS (Bulletin Board Systems) was the first sign of existence of a greater digital world, a portal that you’d log on to to read online news and bulletins and exchange messages. I began working on BBS in 1996, but when 1998 rolled around, it brought with it more mainstream adoption of the worldwide web. My attention was instantly diverted and BBS messages started to quickly dissolve as open email servers came into play.

2. You’ve Got Mail!

One-off messages -- incoming and outgoing -- were simple, functional, and fun. The intrigue of wondering who could be sending a personal message that lived in your own private, digitalized mailbox was thrilling. People became hooked. Email’s popularity transcended generations as servers like AOL, Hotmail, and Yahoo gained speed. There was the excitement of an entirely new form of human communication, and one accessible to anyone, from anywhere (or rather the nearest computer with dial up or Internet cafe). Email exchanges then became organized into threads, turning one-off messages into on-going, contextual conversations. This reorganization was the greatest innovation we’ve seen in email thus far.

The early, viral popularity of email is not unlike what we see with modern social services such as WhatsApp, or even Instagram and SnapChat. Simplicity -- minimal features and a drop-dead easy interface -- works when all you’re doing is sending a message or flashing a picture of your double chin. But of course, then email became something more much complex and outgrew the beloved in/out-box. *Cue the scary music...

3. Folders, subjects, and headaches

My head hurts just thinking about it. This is the system we use today, and no one’s arguing that this system doesn’t suck. At this point, what service does it do for you to look through a folder or label with an endless stream of fragmented conversations? If anything, folders and labels breed more disorder within an already disorderly, broken system.

That’s because 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 from each stodgy sent note. The rigid system coerces us to speak in a formal, dated manner that doesn’t exist outside email-land anymore – “Let me loop my colleague in to provide further clarification”, “Please advise” – and it needs to stop. As if the disorderly paradigm wasn’t difficult enough, we sink time and energy crafting emails in a language we no longer speak.

This third iteration hasn’t been completely void of disruption, though. As soon as smartphones came onto the scene, people started checking their email from their phone’s Internet browser, and developers started to salivate with the possibilities. Then, mobile apps entered the scene. Different email apps have taken significant strides toward taming this broken system, as is evidenced by Mailbox’s price tag.

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.

4. Mobile to chat

Consumers around the world have made it clear how they like to communicate –  everything from the slew of messaging apps to abundance of social networks show that the way we communicate has fundamentally changed. If email is ever going to be valuable and, dare I say, fun, again, we need to make conversation a natural, enjoyable part of the process once more by having email reflect how we’ve evolved to talk to one another. This fourth iteration is still in its stages of infancy, or if anything has yet to be seen at all, but soon email will look little to no different than the rich, multimedia mobile messaging we know and love.

Does that mean formality in email will become extinct altogether? No. It just means it will occur like it does in, say, real life, perhaps starting off more formal and gradually transitioning into more a casual dialogue. Unless you actually say “Best Regards” to your coworkers as you leave the office, there’s no reason you should use it when you sign off on messages online, unless you are engaged in a more formal conversation.

In addition, email needs a layer of intelligence that reorganizes messages based on what matters most: people. That means threads should be filtered based on the person, specific groups of people and then everything else (newsletters, subscriptions, etc.). In a world where almost everything is “smart” – almost obnoxiously so – email seems to have pulled the short end of the stick and is void of any form of intelligence. Marrying intelligent filtering with people-centric re-organization will unleash email so it can once again do what it does best: Let us communicate. And this time, it will be from swift, playful mobile messaging interface with the bells and whistles we can’t do without.

Love it or hate it, email isn’t going away (despite everyone trying to kill it). In fact, it’s only getting stronger. It’s still the most-used mobile app today, followed by Web browsing and then Facebook. It is one of the most powerful, open communication platforms we have.

But it’s  lost its way. We’re on the verge of a much-needed tipping point, though, that will finally bring email to life so it can be exciting again.