Slackson comments on What Are You Doing for Self-Quantification? - Less Wrong Discussion
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Some other people are already doing this. I had the vague idea for a while, but only bothered to actually do anything about it after reading Katja Grace's post about Beeminder on OB. The relevant part is this:
I think getting too bogged-down in the details of the system could be harmful in the long run. So far I've got a TODO.txt with a table of tasks I need to do regularly, a table of tasks I need to do just once or very occasionally, and a table for each day where I list the tasks and tally the points. I'll revise the points as I go, but the hard part for me is to get into the habit of using the list.
If you have an iPhone (I don't), you might want to try EpicWin. (A friend just pointed me to this app.)
EDIT: There is actually a previous LessWrong thread on EpicWin and todo list "gamification".