The Problem with Email (aka: MailTags, and how to tag your email)

Two years ago, I stopped filing my email into folders and started indiscriminately putting every piece of non-spam mail into an “Archive” folder on my IMAP server. Somewhere along the way, I started removing attachments to save disk space (that folder is still obscenely large.)

For a while, things were good.

Whenever I needed to find anything in my email, I searched the archive, and I usually found it. But over time, things got slower. And slower. And recently, searching mail has actually become a bit of a chore in Mail.app. When I’m disconnected from the internet, searches are blink-of-an-eye fast because Mail searches an index of its locally cached mail. When I’m connected to the net, I wait and I wait. And it sucks. It sucks because computers are fast, and people shouldn’t need to have to wait on them anymore.

But the slowness isn’t the real problem. The real problem is that there are TOO MANY MESSAGES. You see, when disk space is cheap, there’s no reason to throw anything away–except it turns out that if you don’t throw anything away, you can’t find anything.

So now each search returns far too many results, and the subject lines of the average email are far too poorly written to give you any idea of what the message contains.

I held out hope that GMail would do search better–but from what I hear from friends who use it extensively, it doesn’t fix the problem. The problem, of course, is that there are nuggets of important information buried in a mountain of text that is your email, and there’s no easy way for you to find them. No magical Pagerank algorithm can help you because you haven’t done the work to figure out what’s important, and the computer isn’t smart enough to do it for you.

Enter tagging.

Just as tagging photos and links help you to find what you want more easily, tagging email might help you to find nuggets of information more quickly. Instead of stuffing an email in a single email folder (associating it with, at most, 1 topic area), you could associate it with three topics–or a dozen–and easily find it by referencing any of them later. Your minimal effort up-front would pay off in intelligent search results later.

For the past month I’ve been beta-testing a Mail.app plugin called MailTags. It’s focus is not, unfortunately, to allow you to easily tag your email. Rather, it adds some useful project-management features to Mail.app. Incidentally, you can use one of the fields it adds to tag your messages.

It doesn’t solve The Problem with Email. But I’m hoping that someday it will.

In the meantime, check it out. It’s GTD-friendly. And it’s useful in its own right.

Link: MailTags plugin for Mail.app