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There are a number of sites that provide more-or-less this service! (except you're paying them if you fail to keep your commitments, not your friend) Examples include StickK, Beeminder and TaskRatchet (full disclosure - I do some part-time support work for Beeminder). Just as you describe, you make a commitment, either a one-time one (paint the bedroom by Friday) or an ongoing one (go to the gym 3x week), and pay up if you fail. Some of them link to independent sources of data (your stepcount on Fitbit), so it's harder to claim you've done something when you actually haven't.

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Thanks for the comment, Clive! I was aware of the existence of Beeminder, but was too lazy to research what other tools exist now. Thanks for doing that research for me!

As I say below to Daniel, I tried Beeminder several years ago but it didn't take. Maybe I'll check it out again, and the other ones you mention.

One thing the text-message + Venmo thing has going for it is maximum user simplicity. But that simplicity means limited functionality - no obvious way to set up recurrent things or tracking data and so on.

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Amen! We've been saying this for years about how bad anti-charities are: https://blog.beeminder.com/anticharity/ (oh dang, that post is over a decade old now)

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Great piece! I must admit, I tried Beeminder maybe 7 or 8 years ago, and it didn't stick because I found the interface too complicated to be habit-forming. But that was a long time ago, maybe I will take another look!

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