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In this "Lessons" episode, we explore what I call the "Expert's Burden" - why gaining more expertise actually makes you feel less certain, not more. It's a fascinating paradox that hits every high performer: the more deeply you understand your field, the heavier each decision becomes.

Through research and real-world examples, we'll unpack why the best operators often sound the least certain, and why that growing uncertainty isn't a weakness - it's actually your evolved understanding expressing itself. Whether you're a founder, investor, or leader, understanding this phenomenon will transform how you think about expertise and decision-making.

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Yudkowsky on My Simplistic Theory of Left and Right - By Bryan Caplan and Eliezer Yudkowsky