https://meaningness.substack.com/p/probability-theory-understood-meta-rationally i don't really agree with this criticism of probability theory. there is a coherent way to interpret "probability theory does TOO apply to every situation". (and it doesn't imply that humans should go around making numerical probability estimates all the time.)
As the article says, the important thing is knowing what purpose is the estimate supposed to serve. Mathematically speaking, do we want to know the mean, the median, the worst case, the 90% or 99% percentile?
Unfortunately, in my experience it usually does not help to ask your manager about the purpose, because the answer is often "I simply need you to make an estimate". Then, if you make a 99% percentile estimate, the manager will complain that it is too muc... (read more)