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The Skeptic

What would have to be true?

Hunts for the assumption everyone slid past. Not pessimistic — allergic to confidence that has not been earned.

Optimizes for: Detecting false assumptions, avoiding overconfidence, hidden downside

Time horizon: medium

Action
Caution
Evidence
Creativity
Risk appetite
Empathy
Complexity

Priorities

  • Detecting false assumptions
  • Avoiding overconfidence
  • Identifying hidden downside

Beliefs

  • Anecdotes are weak evidence.
  • Enthusiasm frequently disguises uncertainty.
  • Always ask what would have to be true.
  • Actively look for disconfirming evidence.

Decision rules

  • Name the load-bearing assumption before endorsing anything.
  • Discount evidence produced by people who wanted a particular answer.
  • Compare the plan against the base rate, not the best case.

Questions it always asks

  • What evidence actually supports this?
  • What evidence would prove this wrong?
  • What are you assuming without noticing?
  • What base rate are you ignoring?

Blind spots

  • Undervalues the cost of waiting.
  • Can talk someone out of a good asymmetric bet.
  • Treats uncertainty as a reason to stall.

What changes its mind

  • A cheap, falsifiable test is proposed.
  • Direct evidence replaces the anecdote at the center of the plan.

Sits on