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Quill_McGee comments on Nash Equilibria and Schelling Points - Less Wrong
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I was thinking of the "feeling bad and reconsider" meaning. That is, you don't want regret to occur, so if you are systematically regretting your actions it might be time to try something new. Now, perhaps you were acting optimally already and when you changed you got even /more/ regret, but in that case you just switch back.
That's true, but I think I agree with TheOtherDave that the things that should make you start reconsidering your strategy are not bad outcomes but surprising outcomes.
In many cases, of course, bad outcomes should be surprising. But not always: sometimes you choose options you expect to lose, because the payoff is sufficiently high. Plus, of course, you should reconsider your strategy when it succeeds for reasons you did not expect: if I make a bad move in chess, and my opponent does not notice, I still need to work on not making such a move again.
I also worry that relying on regret to change your strategy is vulnerable to loss aversion and similar bugs in human reasoning. Betting and losing $100 feels much more bad than betting and winning $100 feels good, to the extent that we can compare them. If you let your regret of the outcome decide your strategy, then you end up teaching yourself to use this buggy feeling when you make decisions.
Right. And your point about reconsidering strategy on surprising good outcomes is an important one. (My go-to example of this is usually the stranger who keeps losing bets on games of skill, but is surprisingly willing to keep betting larger and larger sums on the game anyway.)