Cicero's contemporary, the Roman financier Crassus, was the wealthiest man in the ancient world — and died chasing one more deal. Medieval Jewish philosopher Maimonides, writing in his Mishneh Torah, identified a subtle trap he called 'acquired habit overriding judgment': the longer we practice a skill, the more we conflate fluency with accuracy. In finance, this shows up as the veteran investor who reads a balance sheet faster than anyone in the room but stops noticing when the thing they're reading no longer reflects the actual business. Speed of analysis is not the same as quality of analysis — and the two start diverging precisely when you feel most confident. The practical move is low-tech: before finalizing any significant financial view, write two sentences about what this company, instrument, or position would have to look like for your thesis to be completely wrong. Not 'what are the risks' — that's a list. Two sentences about structural wrongness. Fluency is an asset. Unexamined fluency is a liability dressed as expertise.

What would someone observing your last three financial decisions say about the gap between how long you spent analyzing and how long you spent questioning whether you were analyzing the right thing?

Drawing from Medieval Jewish Philosophy / Maimonidean Ethics — Moses Maimonides