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If you find yourself needing a spreadsheet with dozens of assumptions to evaluate an investment, it probably belongs in the Too Hard Pile.
When evaluating the complexity of an investment or business decision
Poor Charlie's Almanack / Berkshire Hathaway Shareholder Meetings
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If someone's behavior seems irrational, look at the incentive structure first -- you will almost always find the explanation there.
When diagnosing seemingly irrational behavior in individuals, organizations, or markets
The Psychology of Human Misjudgment (Harvard Speech, 1995)
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If multiple cognitive biases are pushing in the same direction, expect an extreme outcome (Lollapalooza) and be extra cautious.
When analyzing situations with extreme crowd behavior, market bubbles, or cult-like dynamics
The Psychology of Human Misjudgment (Harvard Speech, 1995) / Poor Charlie's Almanack