There are a number of technologies that I seem to be a perpetual early adopter of, but they don't quite work. Voice recorders is one (and I'm
working on one that I think I'll use). Another major one is todo lists.
I use todo lists in software source code, in
iCal, in
OmniOutliner, in text editors, in my email drafts folder, in email sent to myself (and my inbox in general), etc.
Still, the only todos that actually work for me are the ones that I inject into the workflow of my life, somewhat analogous to the
method of loci approach to memorizing. E.g., I put a note on the door that I'll be exiting in the morning to remind myself of critical things to take to work; I open up an email and leave it on the screen if it needs to be addressed when I next open up my laptop; I rearrange objects so that they'll naturally be there when I need them, such as keys, sunglasses, cell phones; I'm a firm believer in having a designated location for each object, so that I in the worst case only need to search one box, for example.
It may be that I'll someday adopt a device that I'll always have with me, that can sync up with anything I do on computers. Cellphone PDAs can do this, although they could use better UI for todos.
In the meantime, I think what I'd really use is a todo list that supports both priorities and tagging (or classification), and is able to alert me of todos based on the tags and priorities, rather than dates and times for each todo. Let me explain why, and what I mean.
What I mean is that I'd like to be able to trivially mark a todo as a "don't leave for the office without it" item, or a "do this before going to bed" item, or a "remind me every day or so, but make sure I get back to it in 1-4 weeks" item, etc. There aren't many categories like that that matter to me, but I'd like the computer to understand them well, including being able to trivially take hints about my level of tolerance for distraction, or figure out that there's a build-up of small tasks that will need a solid block of time to get done, and
possibly go into things like understanding which items require access to help desks, in what time zone, etc.
I'd like to be able to have a dashboard of different types of tasks, and be presented with concise lists of immediate actions at the appropriate times, such as "whenever I turn on my computer in the morning," or "before I'm likely to leave work, taking into account whether I've been at my desk most of the time during the day, or the computer has been largely idle, which is a sign of meetings, and means I may abruptly turn off the computer and head out."
Setting a date and a time for a todo item maps very poorly to the problem. It was appropriate for pen-and-paper systems in the last century, but it's not appropriate to modern computing systems. I think it's analogous to the problems with
naming a computer file when you create it: 1) you don't have the context to make that decision at the time you create the item or file, and 2) the action isn't a highly creative task requiring such an open-ended solution, but is rather quite constrained to follow a few simple patterns, such as "morning task" or "evening task," or "my work started on day x on subject y, and I'm not quite sure what y is yet, and I'll use search to find it anyway."