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Re:Show HN: When my builds fail I pay money to charity by compiler-guy on Monday May 07, 2018 @02:31PM (#17015154)
You are not accounting for the fun that doing this entails. It's gamification of the build with a gaming partner that is actually fun to play with.

When I play a game with my buddies, I try to win, but even if I lose I still have a good time.

This is a very similar concept. Also, don't assume that this is the only money he gives. Games are fun.

Re:Show HN: When my builds fail I pay money to charity by TeMPOraL on Monday May 07, 2018 @11:57PM (#17018707)
In reality I was just nitpicking. Doing the win-win strategy I described does require more willpower, and I understand that one employs tricks like these to avoid using willpower.

Incidentally, I somewhat envy people who are capable to pull such strategy off. It requires some amount of suspension of disbelief, forgetting for a moment that you're the game master and playing the game by the book way past the point it's become uncomfortable. I don't have that. I tried many times, but my mind just refuses to participate in self-trickery.