Coaching practices for Expected Value Thinking Deciding Under Uncertainty After a Loss

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Does this sound like the set of challenges you might be facing?

  • I keep passing on bets that are clearly worth it over the long run, because the sting of the likely small loss looms so much larger than the rare big win
  • The math says this bet is worth taking, but if it goes wrong the loss would genuinely wreck me
  • I made a call that turned out badly and now I feel like an idiot for it
  • I keep playing out this decision in my head as if there’s just one way it goes
  • I make these probability guesses in my head

Practices that may help

  1. Expected Value Thinking: Deciding Under Uncertainty
    Expected value thinking multiplies each possible outcome by its probability and sums the results, giving a single number that represents the average payoff of a decision. It is the mathematical foundation of rational decision-making under uncertainty — well grounded in decision theory — but it has real limits: probabilities are often uncertain, outcomes are not always quantifiable, and raw expected value ignores risk aversion that can be legitimate.
  2. Accept positive-EV decisions even when they feel uncomfortable
    If the expected value is clearly positive, take the decision — even if most individual outcomes are losses.
    Expected Value Thinking: Deciding Under Uncertainty
  3. Adjust raw expected value for risk aversion on large stakes
    A 50% chance of losing everything is not equivalent to a certain 50% loss — adjust for your actual risk tolerance.
    Expected Value Thinking: Deciding Under Uncertainty
  4. Judge decisions by the process, not the result
    A good decision that produces a bad outcome is still a good decision.
    Expected Value Thinking: Deciding Under Uncertainty
  5. Enumerate scenarios and their probabilities before deciding
    Write down each meaningful outcome, assign a probability, and compute the weighted total.
    Expected Value Thinking: Deciding Under Uncertainty
  6. Keep a decision journal to score your EV estimates
    Log your probability estimates and payoff predictions, then compare them to what happened.
    Expected Value Thinking: Deciding Under Uncertainty
  7. Use maximin reasoning for high-stakes, irreversible decisions under ambiguity
    Choose the option whose worst plausible outcome is most survivable — when you can’t compute expected value, optimize the floor.
    Ambiguity Aversion — Why Unknown Odds Feel Worse Than Bad Odds
  8. Look for decisions with asymmetric upside — large potential gain, small defined loss
    Seek situations where the worst case is bounded and small while the best case is large and open-ended.
    Expected Value Thinking: Deciding Under Uncertainty
  9. Score decision quality separately from outcome quality
    Judge the process you used — not whether it worked — when you review a past decision.
    Decision Journaling: Learning to Decide Better Over Time
  10. Thinking in Bets
    Annie Duke's thinking in bets framework treats decisions as bets with uncertain outcomes, separating the quality of the decision from the quality of the outcome. Most real decisions involve incomplete information, so good decision-making is about process and probability, not about being right every time. The core skill is evaluating decisions on the information available at the time, not on how they turned out.

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