Coaching practices for Expected Value Thinking Deciding Under Uncertainty Before Bed

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

  • I keep playing out this decision in my head as if there’s just one way it goes
  • There’s a tangled decision with too many moving parts to hold in my head all at once, and I feel pushed to just call it now and be done
  • I make these probability guesses in my head
  • This is a one-way door
  • There’s a chance in front of me where the worst case is small and survivable

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. 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
  3. Sleep on important decisions
    For complex decisions, delay commitment overnight — sleep processing integrates information deliberate thought misses.
    The Three Bs of Creativity: Bed, Bath, and Bus
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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.
  9. Calculate the expected value of gathering more information
    Before researching further, ask whether the additional information is actually worth the cost to obtain.
    Expected Value Thinking: Deciding Under Uncertainty
  10. Distinguish risk from ambiguity before reacting
    Label whether you’re facing known odds or genuinely unknown odds — the right tool depends on the answer.
    Ambiguity Aversion — Why Unknown Odds Feel Worse Than Bad Odds

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