Beeminder, as others have mentioned, handles #1 and #3 pretty well (minus the donation to the KKK part - the money for failing goes to Beeminder). I built GTBe

Beeminder, as others have mentioned, handles #1 and #3 pretty well (minus the donation to the KKK part - the money for failing goes to Beeminder). I built GTBee[1] using the Beeminder API which is pretty much #2. Again, the punitive thing is taking your money, starting at $5 and escalating from there. This isn't to say that it wouldn't be a fun project to build things that do this though! [1] https://itunes.apple.com/tc/app/gtbee/id779525180?mt=8 https://itunes.apple.com/tc/app/gtbee/id779525180?mt=8