I recently thot about Courage, and the fact that most people are too afraid of risk (beyond just utility concavity), and as a heuristic we should be failing more.

This instinct may be related to The Fear of Common Knowledge. We seem afraid to attempt things that can provide common knowledge of what our ability levels are. In other words, if I only try things that are safe, or are so challenging that I can't reasonably expect to succeed anyway, then nobody including myself has to acknowledge just how dumb, or untalented, or ignorant I am. But if I try and fail at something that's only somewhat challenging, then things become awkward.