Cultivate a habit of confronting challenges - not the ones that can kill you outright, perhaps, but perhaps ones that can potentially humiliate you.

You may be interested to learn that high-end mountaineers apply exactly the strategy you describe to challenges that might kill them outright. Mick Fowler even states it explicitly in his autobiography - "success every time implies that one's objectives are not challenging enough".

A large part of mountaineering appears to be about identifying the precise point where your situation will become unrecoverable, and then backing off just before you reach it. On the other hand, sometimes you just get unlucky.