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Emile comments on Rationality Games & Apps Brainstorming - Less Wrong Discussion
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Time estimation app
At the beginning of each week, enter the things you plan to do during the week, the probability that you estimate of doing them, and the percentage of time you'll spend on various distractions (eg. if you use Rescuetime to count hours of distracted browsing, or the number of movies / TV Series you'll watch during the week), again with confidence intervals.
Then, by the end of the week, you can check your score, and compare it to others!
(This doesn't require a dedicated app, it could be a spreadsheet in google docs shared between a few people, with their email/contacts so they can remind each other to fill in the table once the week is over)
I try to do this by hand, but this would be much more convenient. Also, in addition to using it as a rationality training tool I would be interested in a program that collects this data and then uses it to directly help me make predictions about future projects.
I already do this on PredictionBook.
Much to everyone else's chagrin.