GreenRoot comments on Rationality Lessons in the Game of Go - Less Wrong
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I find backgammon to also be a good analogy for life in general, though I don't really have the time to get into all of the details... perhaps the most important lesson, though, is that if you always take the "safest" move, you're almost guaranteed to lose! You need to take risks - smart risks, where the payoff is worth the danger and the danger is non-fatal, but risks nonetheless.
And sometimes, even if you do everything right, you still lose. That's life.
There's an interesting essay by William Pinckard that contrasts the philosophical perspectives of the gameplay of three ancient games; backgammon, chess, and go, which says in summary: backgammon is man-vs-fate, chess is man-vs-man, and go is man-vs-self.