For some reason, capturing (and managing) todos seems to be a difficult problem for technology tools. Every once in a while, my brother and I wind up going on about this. I'm not sure if this is a technology problem or a people behavior problem, but for whatever reason, the right tool always seems elusive.

Years ago, I used a piece of paper. The top left was short term todos, the top right was people I needed to call, and the bottom was longer term projects I was focused on. I'd edit, scribble, and mark over, then when I could no longer read the page, I'd rewrite it, which was a good time to clear out junk. This system worked pretty well.

Then I got a Palm Pilot. One of the original ones, back in 1993 or something like that. (In fact, I re-tried it a few years ago and it still worked! Even the 13 year old software worked on Windows. Take that!, Microsoft-haters!). It was fine for calendar and contacts, but useless for todos as they took too long to enter.

Thats more or less been the history of it: RememberTheMilk, or ReQall, or (gasp!) even Org-Mode seem to be good for a kind of work, but not for all of it. Why?

Sometimes its that old data entry problem again. ReQall fixes this somewhat as you can enter items via speech, but I've found it seems to "forget" my todo status at times. If your todo program doesn't remember, um, what good is it?

But leaving that aside, I think the problem is one of definitions. There are todos we really intend to do ("Pay Mortgage"). In fact, some we're really wasting our time writing down as we won't forget them anyway ("Get downpayment for house"). Some are aspirational ("Go for a swim") - we might do it, or we might not, and there is no project that depends on them, so they tend to sit, accumulate, and clog up the todo list. So then we delete 'em. So much for those todos.

Other todos are transient - effectively they expire. "Build Snowman" doesn't work well once the snow has melted. We don't know when its going to melt, but, before it does, we want to build one. When the snow melts, the todo has expired. Can't it just go away and stop clogging up the todo list? (In fact, some bookmarks and contacts are like this: they're related to something we're doing near time, but after trying to find a plumber or research a todo tool, we no longer need the contact/bookmark: Can't they just go away? Has anyone invented one of these?)

Some todos are kind of floating ideas ("Install new todo software"). We do intend to do it, sometime, when we've got spare time. But not actually now. We're busy now. We don't want to delete them, because life would change somehow, if we ever did it. But….

These todos also clog up the todo list.

There are probably others. But I think this taxonomy of todos is the real problem, regardless of the product (or system, for GTD advocates).

Thats why a piece of paper works so well for all those unforgettable, or aspirational, or floating, or transient todos.