When you replay your old choices, remember you made them with less information than you have now.

Judging a past decision with present knowledge is not a fair test. You know how it turned out, which is exactly what the earlier version of you did not have, and that makes the right answer look obvious. The question is whether it was reasonable given what was in front of you.

Take the decision you keep revisiting and write down what you knew at the time, nothing more. Then ask whether a sensible person with only that list could have chosen differently. Usually the answer is no, which is where the replaying can stop.