Outside of games, I put a lot of time and effort into trying to stay organized. I've tried various systems and tools, and I usually gravitate back to some variant on Getting Things Done, usually to good effect. The main thing I've learned in this is that while specific tools (processes, software etc.) can be neat and fun in its own right, what's important is understanding what you want to do and why so that your system solves _your_ problems.
When I was younger, I thought of the idea of maintaing task lists or neatly labeled file folders as uselessly anal retentive. Why exert the effort on such things when you could just be doing cool stuff instead? This was a pretty useful all purpose excuses to get out of a lot of responsibilities, but at the time I at least thought I was being sincere. And I probably was, but I was also being kind of stupid.
The purpose of a good system is not to do *instead* of the cool things, it's to *enable* the cool things. It carves out space for thought, freedom and creativity by removing uncertainty, doubt, fear and all the other little obstacles that you may not notice but who are responsible for you getting to the end of the day and wondering why you didn't write, or play video games, or go out or whatever was important to you.
Now, implicit in this is an idea that I think was best summed up by Merlin Mann as "You don't need to set a reminder to play your video games." There are things in your life which you don't need to organize because they're what you really want to be doing - the purpose of setting up a system is to build a structure around those things so that you can get to them without worrying about all that other stuff.
This concept is directly contradictory to one of the major tenets of contemporary RPG design, where it is expected that rules drive towards your fun things, and that you will pick a game based on which rules do so most successfully. I've never been terribly comfortable with that idea, but articulating why has always been a bit of a trick, and only today did I stop and compare it to putting "Play Xbox" on your todo list. And the more I think about it, the more it holds up.
Partly because it's not so clear cut as good/bad. There are times when I _will_ put "Play Xbox" or equivalents on my task list. Not because I'm going to forget that I want to do it, but because some other factors (like a very busy day) make it useful to me to put in a reminder to take a break and prioritize myself form time to time. Game rules can certainly do that.
And, in fact, rules can do a lot of useful things. This should absolutely not be considered an argument against RPG rules in general. But it is me wondering if having rules for the part of play you love is automatically the best use for rules.
1 - I still fail this more often than I'd like. But when I do, It's usually pretty easy to track back to the source.
2 - Though if they do it a lot, I wonder what else is going on in the game (either in the system or at the table) that keeps making people forget what they want to do.
3 - Yes, blah blah blah, fruitful void. I'm not talking about theory discussion. I'm talking about how games are designed, used and clung to.