Earlier quoted context omitted.
I think about this all the time myself. Have you looked into StikK? They provide services like automatically donating to your most hated charity if you don't meet your goals (they provide options like the NRA and Planned Parenthood).
No haven't heard of them but sounds like beeminder. In my opinion these automated solutions seldom work in the long run. Otoh having a real human being who calls you up or even WA you to check how you're doing from time to time can make a hell of a difference (right now my wife does that for me in a good way :P but I really think the guys who started bossasaservice were on to something and people were going crazy abo…
Beeminder cofounder here. Can I hear more about why you think this? There are definitely people for whom Beeminder doesn't work at all but you sound like you're making a different claim -- that it may work for a while but then stop working. That's the opposite of our experience. Our churn numbers get really good for those who stick around for a year and anecdotally we have lots of people getting PhD theses written thanks to Beeminder, etc.
But if you've had short-term success with things like Beeminder -- https://blog.beeminder.com/competitors -- and then had it fail, that would be valuable to hear more about.
Oh, and I should mention that Beeminder isn't necessarily entirely automated. If you derail and are about to be charged money but don't agree that it was a legit derailment, you talk to a human about that.