Serendipity/zemblanity has almost completely replaced optimism/pessimism in my mental models. Fairly easy swap-out, dramatic results.
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Sounds same as, in Taleb's terms, an antifragility/Procrustean bed fragility dichotomy
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Not quite. Taleb refuses to go all the way to fully embracing serendipity. He applies the idea more narrowly to risk avoidance.
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Not seeing that, unless you say narrowness has to do with 1. focus on payoff over prob. or 2. preference for apophatic epistemology
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See his antifragility concepts alongside his "neomania" criticism and older-is-better heuristic.

