Coaching practices for When I'd Swear I Know Roughly Where a Number Lands the Real Answer is Constantly Outside the Range I'd Have Bet on I'm Way More Sure of My Estimates Than I Have Any Right to Be

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

  • When I’d swear I know roughly where a number lands, the real answer is constantly outside the range I’d have bet on
  • I land on a number and just go with it, never pausing to ask what’s the most it could possibly be or the least
  • I tend to blurt out one confident-sounding number and act like it’s solid, when honestly I have no business being that sure
  • I’m staring at a question that feels totally out of reach, and it never occurs to me that I already know one solid number nearby that I could just scale up or down from
  • I slap a confident-sounding percentage on things I genuinely have no basis to estimate, just to seem rational

Practices that may help

  1. Practice confidence interval estimation
    Estimate ranges for factual quantities and check how often the true value falls within your range.
    Calibration Training
  2. Sanity-check against known extremes
    Test your estimate against the clearly too-high and too-low bounds to calibrate your range.
    Fermi Estimation
  3. Estimate in ranges, not point estimates
    Instead of "my estimate is 500," say "I think it is between 200 and 2000."
    Fermi Estimation
  4. Anchor on what you know and scale from there
    Start from a number you are confident about, then reason to the unknown.
    Fermi Estimation
  5. Distinguish uncertainty (quantifiable) from ignorance (unquantifiable)
    Know when you can assign a probability and when the situation is so novel that a number would be fabricated.
    Calibration Training
  6. Think and communicate in explicit probabilities
    Replace vague language ("probably," "likely") with numerical probabilities.
    Superforecasting
  7. Check units and scales for consistency
    Catch order-of-magnitude errors by ensuring your units are consistent across the estimate.
    Fermi Estimation
  8. Practice probabilistic calibration by tracking your predictions
    Assign explicit probability estimates to your predictions and track whether they come true at the right rate.
    Base-Rate Neglect: Why We Ignore the Odds
  9. Translate beliefs into bets to reveal your true confidence
    Would you bet $100 on that belief at even odds? The answer often reveals the gap between claimed and actual confidence.
    Bayesian Thinking: How to Update Beliefs Rationally
  10. Track your estimates and calibrate
    Compare your Fermi estimates to actual figures when you can, and use the gap to improve future estimates.
    Fermi Estimation

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