I teach quite a bit about structuring problems to help make decisions. Usually models can help illuminate the tradeoffs, and sometimes it becomes much more clear what the right strategy is.
But sometimes the downside of the “right” decision comes to dominate the thinking of the decision maker. This is a fundamental part of the dilemma facing the contestant on the game show Let’s Make a Deal when they are offered the chance to change their original decision. Even if they are better off changing, the emotional pain of changing and then losing makes them stay with their first choice. They can hear their friends saying “You won the car and then you gave it away.”
Here’s an interesting article about football coaches going for it on fourth down. I am not sure about all the details of the study, but it is probably true that the thought of what the sports writers and talk radio people will say play an important part of the calculations of when to try or punt.