In the end this is a trivial decision making rule: I am very aggressive when I can gain exposure to positive Black Swans—when a failure would be of small moment—and very conservative when I am under threat from a negative Black Swan. I am very aggressive when an error in a model can benefit me, and paranoid when the error can hurt. This may not be too interesting except that it is exactly what other people do not do. In finance, for instance, people use flimsy theories to manage their risks and put wild ideas under “rational” scrutiny. Taleb, Nassim. The Black Swan (p. 296). Penguin Books Ltd. Kindle Edition.
This must be your approach. Use BS to your advantage
Balaji Srinivasan for positive black swans; Whatifalthist for protection
Implement the "barbell strategy": be hyper-conservative in 1 and extremely aggressive in 2.
Barbell strategy: being hyper-aggressive and hyper-conservative instead of being mildly aggressive or conservative. On one hand, you’re creating a safe ground investing 80-90% of your capital into extremely safe instruments—that is your insurance policy against negative black swans. On the other hand, you’re generating a serendipity attraction machine investing 10-20% of your portfolio into incredibly speculative bets with extremely high upside (like venture capital, crypto, etc) that way you’re exposing yourself to positive black swans. You have no risk and high risk which averages out to medium risk but contains an exposure to positive Black Swans.
Connects to R: Psychology of Money that said that most gains in life are result of a few inputs—i.e., black swans.