Now onto email: Why isn't there a good email solution?

I've been thinking about this for a while, then it congealed a few weeks ago, and immediately after I heard of Mailbox and their meteoric rise. Clearly email is something that is important to people, and, incredibly, it hasn't been solved yet. And Mailbox doesn't quite fit the bill either, but the insane interest clearly demonstrates there's a big demand for something better.

My solution starts with my inbox management system. I adapted it from part of Dave Allen's GTD (Getting Things Done) system, and I've been practicing it religiously ever since, this is, for around 8 years now, and I always have inbox-zero every day, many times a day, I never have an email fall through the cracks, and I always have a stress-free, even joyous relationship with my email. Who else can boast of that? Not many people! And the system is really really simple, too.

The system is based on the idea that your inbox is an inbox. Things start out there, but they must not stay there. When you go through your inbox, every single email needs to leave your inbox before you're done. I use Gmail, because it's the greatest tool for email, but their web interface sucks (it didn't used to, but it started drifting and getting slow years ago, and the new design has made it much much less usable).

Here's how you check your email:

  • Go through each email, one by one
  • Read it, or, if it's long, skim it.
  • Decide whether you can do what you need to do and be completely finished with this email forever in 2 minutes MAX. If you can, do it, now. It'll take longer to file it and get back to it later. Then archive it.
  • If it's going to to take longer, star it, then archive it.
  • If it's a ticket or something you're going to need later, put it in a Tickler file (this term comes from Dave Allen)

That's about it. About half my email is dealt with immediately, about half ends up in starred, and now my inbox is empty. Done.

Now the discipline is to remember to check your Starred folder. And to have the discipline to tackle those annoying starred emails that you know you need to do but really don't want to. But that is a time management issue, not an email management issue, and I recemmend Brian Tracy's "Eat That Frog" to deal with that.

You must maintain an empty inbox and star the emails that you need to deal with and then work off your starred folder when you need to work emails. Ideally, of course, your emails should become tasks on your to-do list that you prioritize as you want to, along with whatever tasks you have that did not originate from email. The danger is that email-originated to-dos somehow end up being arbitrarily prioritized either higher or lower than other tasks, and you must ensure they get their proper prioritization. Again, go read Eat That Frog.

I also advocate going through your starred folder at least once per week and cleaning it out completely. Sometimes you'll have to leave one or two emails for next week, but if they're still there a week later without a good reason, it's a red flag.

Here's an important feature that's part of the email system I designed, but that I'm no longer actively practicing, because I haven't found any tool that allows me to it in a practical way: A "Waiting for" flag that you can set when you send an email that says "I need a response to this email, and if I haven't gotten one in x hours/days, alert me". This is great for all those situations where you send an email to a colleague or a vendor or someone, you can say "remind me to check if I heard back the day after tomorrow". This way when you send an email, you can clear it from your mind completely, knowing that you this is now out of your court, and onto theirs, unless they don't respond, in which case you'll be notified. Getting things out of your head is critical to peace of mind.

With Gmail I used to have a "Waiting for" label, but when sending emails, it's cumbersome to have to go into the Sent folder, then add the label. And I'd have trouble remembering to go and check the Waiting for label, because it's not up there near Inbox and Starred. So I abandoned it instead.

Of course, you also need to be able to set it on incoming emails. This is great for order acknowledgements - you can say "remind me in 3 days to check if this package actually arrived". When it arrives, remove the "Waiting for" flag.

So here's the simple tool that I'd like to see:

  • An inbox with an easy way to reply, reply & archive (I love the Send & Archive feature of Sparrow), archive, delete, Star, mark as Tickler (with optional date) or Waiting for (with optional date).
  • Easy way to navigate to Starred, Tickler, Waiting for.
  • Bonus points for being able to make a few additional lists that are just as easy to use as the built-in ones. That is, the same shortcuts apply to both filing into those lists, and to navigating to them. It's okay if there's a hard limit to how many of these you can have, for UI reasons.
  • When you've sent an email, something stays on the screen allowing you to set "Waiting for" on it.
  • Navigating to other folders/lists, including Sent, is quick, because it remembers everything you've sent in this session without having to round-trip to the server
  • Some playful UI element that encourages people to keep their inbox empty
  • And the Starred folder is visually designed to be the natural workplace, as opposed to the inbox
  • Getting things back to the inbox is not easy
  • However, there's an easy undo on every move. When you've archived, you can just hit undo, and it's back. We want to give people the confidence to go through their inbox quickly without having to be afraid of making a wrong move. Perhaps we even need to let the email stay in the inbox a little bit with an element that shows what you just did to it, as an acknowledgement and verification and to offer you a chance to undo.

If we simply get this right, that would be a better tool than any other tool on the market that I know of.

There's a question of mobile vs web vs desktop. I'd probably vote for iPhone + web. Mobile is where a lot of email gets checked, desktop is where a lot of the work gets processed (starred folder). And I'd probably build on top of Gmail, like Mailbox. No need to solve that problem again. We're only innovating at the user interface level.

I'd probably stop there, but if we get a solid business going here (and I believe you could easily charge for this, even if it's built on top of Gmail), we could move into the to-do space. The thing is that the stuff in your starred folder really needs to be part of a global prioritization of work, so either you'd need to integrate with some external to-do list app like Things, or you'd want to build to-do list features into this app. Both are options. The to-do list market is very big as well, but also has many well-established players, and seems to have better solutions than email and notes.

What Mailbox does right is it lets you quickly move things away from your inbox. What it does wrong is its primary feature, the "Remind me later" feature then throws the email right back into your inbox later. That's a no-no in my book. Another problem is the categories - "Later today" … I want this email to go away from my inbox now, but then when I get back in front of a computer - it could be in an hour, it could be in 3 - then I want to get to it. With Mailbox, that's confusing.

Another thing that I find odd is how it insists on creating its own labels prefixed with [Mailbox]. That just makes it so much harder to use Mailbox along with other clients, like the web client or Sparrow. Just make them labels.

Again, I'd love to see this tool, I think it would make millions of people more productive and give them more peace of mind, and I think there's a large number of people who would actually be willing to pay for a service like this - email is so critical to most of us, we spend so much time on it, if we could make it more efficient and joyful and stress free, it's a huge win. Might even save lives. I'm serious!

But I'm busy with other projects, so I'm not going to get around to doing this myself anytime soon, so if you would like to do it with me as a partner, I would love to be part of that. Just get in touch. Or if you want to do it on your own, go ahead. Just give me a free account for life ;)



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