[acrefoot]

I really like the ideas in Annie Duke's "Thinking in Bets". The book would suggest that the rightness of a decision shouldn't vary much with the outcome (or with time).

The book suggests that we judge the quality of the decision based on how comprehensively we evaluated possibilities before we made the decision. Our habit is to re-evaluate the quality of the decision based mostly on the outcome, even if that outcome was one of the possibilities we considered. The book suggests that a good decision can't be judged by the outcome alone, as every decision is a bet with a variety of possible outcomes. (Adjusting priors for future decisions is related to this, and one should strive to allow adjusting priors in a disciplined way while not beating oneself up or congratulating oneself too much based on outcomes which were not certain going into the decision.)

You can luck into winning the lottery, and luck into really bad outcomes while investing into index funds, but that does not make playing the lottery a good decision. In fact two decisions that lead to the same outcomes should be respected differently, depending on how much work went into them and the quality of the decision-making framework(s) applied.