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Vaniver comments on Motivation and Merciless Commitment Contracts - Less Wrong Discussion
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A common suggestion with these sort of contracts is to do things you will succeed at in order to get used to succeeding. If you say "I will either lose $100 or ask out the person I like," and then you don't ask them out, then you end up $100 poorer and less confident than you were before. (This is a pretty big risk for a confidence building measure!)
Compare to something like "I will either lose $100 or smile at the person I like this week." Likely to succeed, grow a bit, and be ready to step things up a bit next time.
I also recommend seeing a professional, or getting a book devoted to anxiety alleviation. That seems like a tool much more precisely focused at getting you where you want to be.
When I think about these "precommitment contracts" I anticipate that I'd just fail anyway even if I signed up.
Generally, people make decisions on the margin, and so there should be some contract where making that contract will change you from not doing something to doing something. It does seem to have very different usefulness for different people, though.