The problem with low probability outcome events is that when you repeat the same experiment many times that event can happen with high probability.

I think you should just read the book(s). They're very well written and enlightening.

I guess a hedge in that case would be to try to arrange things so they come out OK if you miss the goal. Like if you want to be president aim for the fail case being a successful lesser politician. Not sure what Taleb says.

Taleb investment advice: put almost all of your savings in super stable investments, like treasuries. Use the rest to bet on unicorn startups, or highly leveraged options (as long as those options have a limited downside and an unlimited upside!). I'm not quite sure how to apply this to one's career.