I know I’m stating the obvious, but email is very very broken.

I have two email accounts, one personal and one for work, and they are both, each in their own way, profoundly broken.  Like most people, I actually have a bunch of email addresses, but they’re logically separated into work and personal.  I use a combination of Gmail and Thunderbird for my personal mail, and Groupwise for my work mail.

I try to manage my personal account so that at least occasionally I get to the mythical zero inbox, but my corporate account with 3,000 messages in it is just a stream that flows by with me on the river bank with a pathetic net trying to catch the most important bits roaring by.  Right at this moment I have 19 emails open on my desktop, awaiting action.

I think that people who don’t work in a corporate environment don’t understand the central role that corporate email systems (Outlook/Exchange, Notes, or Novell’s own Groupwise) play in the lives of their inmates users.  Meetings are scheduled, documents are exchanged, decisions are made, and long-running debates are all handled exclusively within these email systems.  I know that the kids and the Koreans don’t use email any more, but for large organizations, email is practically the system of record for most purposes.  (Xobni Insight for Outlook is supposed to be good, but I don’t have any personal experience with it.)

On the personal, non-corporate side, there have been many runs taken at the Problem of Email.  Notably, there was the  Chandler fiasco; more recent failures were the very nice Seek extension for Thunderbird from the Simile project at MIT, the short-lived “I Want Sandy” email assistant, and myriad universal inbox solutions.

Sandy’s sister, cc:Betty, looks promising, and Thunderbird fork called Postbox has garnered some praise.  I’ve been using the version 3 beta of Thunderbird and I really like it — so much so that I’ve moved back to using a client after switching away for the charms of Gmail.

I think  Google’s Gmail was the first real innovation in email in quite a long time.  For me, the progression goes: mail –> elm –> Eudora –> Thunderbird –> Gmail.  And now, Gmail+Thunderbird.   I don’t like everything about Gmail; the conversation view still baffles me, I don’t really use tagging effectively, I can’t stand not being able to sort by sender, and I don’t understand how it treats deleted and archived messages.  But abandoning the complex folder structure I’d developed over the years was really liberating once I trusted the system.  If there’s going to be real on-going innovation in email, I wouldn’t bet against Google and Gmail Labs.

There’s an excellent discussion of the Problem of Email in the comments to an article by Alastair Croll on GigaOM entitled “Why Email Clients Need to Change.”  The article is worth reading but the discussion is outstanding.

Of the new entrants trying to solve the (personal, non-corporate) Problem of Email, the best one I’ve seen is OtherInbox.  It works with your existing IMAP email to categorize and sort your messages.  It in effect applies preset filters to your messages and seems to be directed at people who have lots of social media updates in their in-box — it groups Facebook messages, for instance.  But it points the way forward, I think, by recognizing that there are actually several distinctive kinds of messages in your inbox, each of which can be dealt with in a different but standard way.

What really got me thinking was, as usual, a visual representation of data; this time, of emails in Croll’s inbox, analyzed using the excellent mail-trends tool.

After all, most email is (relatively)  structured text; Croll had a lot of Twitter traffic in his in-box, but that doesn’t seem to me to be an especially mainstream case.  But it’s one of many, viz.:

Purchases

This is a little workflow; you buy something, the vendor sends you a confirmation.  Then when the order ships, they send you a tracking number.  You need to make sure that the order was correct in the first place and then, perphaps after giving it a relevant name (“new sandals” instead of LL Bean Order #2342423) you want the workflow to keep track of it, perhaps in a calendar view, and update you on its status and throw a flag after a certain period if you haven’t received it.  After acknowledging receipt in the workflow, this thread should be silently archived and disappear from view.  It would be in the interest of, say, Amazon, to offer easy hooks to do this.

Mailing Lists

These have a different behavior than order tracking; they’re best put into a bulletin board view by themselves, with some simple, configurable, rules: keep them in a threaded discussion for two weeks unless I take some other action on them.  Then they can silently fall off the end of the thread, unless they’re subscription or administrative messages, which ought to be archived.

Reminders/Alerts

These are more important and should appear in some insistent form, perhaps in some status bar like Growl — “meeting in ten minutes”, “on a conference call”, “on a call” — and/or on a calendar view.  Then, after the time of the appointment has passed, it should automagically disappear.  No threaded discussion view, no workflow.  But wouldn’t it be nice if your calendar automatically updated your status?

Non-spam ads (opt-in vendor mail)

Spam is at this point a solved problem; I’m thinking instead here of emails from the local minor league hockey team advertising kids’ day or a deal from my garden supply store that I want to know about.  I would set up a rule for these to appear in my main stream but automatically disappear after a day or two.  Linking to the opt-out function as a check box or something would be fantastic.  The hive mind would help a lot here.

Account Info

This category requires special handling; I’d like to see anything with username or password information automatically encrypted and stored.  This function alone would be a major win in my book.

Personal Mail

Anything from a recognized (white-list) sender, especially if it is single-recipient, should go to the top of the stream.  It would be nice to apply GTD-style rules as an option.

Travel

This is a big one for me; I use Tripit to manage my travel itineraries, and I think it’s invaluable.  I email Tripit my hotel reservation and my flight information and it puts it together for me; I’d like my email system to do something similar.  After all, Delta’s itineraries are nothing more than structured text waiting to be parsed into a calendar, status, and archive system.  (This is the classic semantic web use case.)

Other

For me, Twitter and Facebook updates aren’t a big deal, but they seem to be important to some — I can imagine that there are lots of other categories that aren’t relevant to me but are everyday hassles for others.