A necessary part of becoming a better decision-maker is learning from experience. Experience contains the lessons for improving future decisions. Res… - Annie Duke

John Maynard Keynes, one of the most influential economists of the twentieth century, summed up this phenomenon well when he said, "Worldly wisdom teaches that it is better for reputation to fail conventionally than to succeed unconventionally." Succeeding unconventionally carries with it the risk of experiencing failure as a result of veering from the status quo.

Optimism makes you less likely to walk away while not actually increasing your chances of success. That means that being overly optimistic will make you stick to things longer that aren't worthwhile. Better to be well calibrated. Life's too short to spend your time on opportunities that are no longer worthwhile.

Essentially, regardless of the history they have with the decision, they ask themselves, "If I were approaching this decision fresh, would I want to enter into this course of action?"