Uncertainty

June 2026

• Jun 1, 2026ConceptsBetter Decisions Under Uncertainty: A Practical Guide and ToolkitA sound decision can still produce a bad outcome, and luck can hide weak reasoning, so the only thing you can improve is the process. The sharpest figure here is a calibration one: when people say they are 90 percent confident, studies consistently find them right roughly 70 percent of the time. From there it works through availability, sunk cost and anchoring, Gary Klein's premortem protocol, Bezos's two-way door test, and a ten-item checklist.12 MIN1.8k

March 2026

• Mar 5, 2026ConceptsWhat Is Decision Making Under Uncertainty?Frank Knight separated risk, where probabilities are known, from uncertainty, where they cannot be meaningfully assigned, and most big decisions sit on the second side. This guide maps four levels of knowability, then covers satisficing, reversible bets, scenario planning and Bayesian updating. Tetlock's Expert Political Judgment study, spanning about 20 years and more than 28,000 forecasts from 284 experts, found most specialists predicted little better than chance.32 MIN28.0k
• Mar 4, 2026ConceptsProbabilistic Thinking for Enhanced Decision-MakingProbabilistic thinking reasons in likelihoods and distributions rather than certainties, and binary thinking destroys your ability to learn: a good 70% bet that loses gets labeled a bad decision. Annie Duke calls that resulting, judging decision quality by outcome instead of process. Why probably means anywhere from 50% to 90% to different people, how P10, P50 and P90 ranges beat point estimates, and how Bayesian updating works in practice.27 MIN6.0k
• Mar 3, 2026ConceptsRisk vs Uncertainty: What People ConfuseFrank Knight's 1921 line between known probabilities and genuine uncertainty, mapped across a five-step spectrum from casino games to questions no distribution covers. The page explains why optimization gives way to robustness, optionality and heuristics once probabilities stop being meaningful, and uses LTCM's roughly $4.6 billion loss in 1998, the Challenger launch decision and COVID-19 preparedness to show what happens when uncertainty gets dressed up as calculable risk.24 MIN65.4k

November 2025

• Nov 3, 2025Work SkillsLeading in Uncertainty: Making Decisions Amidst AmbiguityIn March 2020 the pandemic erased about 80% of Airbnb's business within weeks, and Brian Chesky had to decide on layoffs, cash and the IPO without knowing how long it would last. Airbnb restructured, pivoted to local and long-term stays, and went public that December. Why known unknowns, unknown unknowns, radical uncertainty and ambiguity each demand a different response, and why projecting false certainty costs leaders their teams' trust.20 MIN32.9k

July 2025

• Jul 12, 2025ExplainersDecision-Making Checklist for Uncertain SituationsWhy structured prompts beat knowing the principles. A 19-item surgical safety checklist tested across eight hospitals reduced major complications by 36 percent and deaths by 47 percent, and the value was not new knowledge but consistent execution under pressure. Klein found expert pattern-matching works with deep domain experience and fails when novel situations get misclassified as familiar, which is exactly when a checklist earns its place.24 MIN20.8k

September 2021

• Sep 6, 2021ConceptsMaking Informed Decisions in Uncertain SituationsFischhoff, Slovic and Lichtenstein measured that gap, and experts are not reliably better calibrated than informed non-experts, since expertise can raise confidence faster than accuracy. The fix is structural rather than attitudinal. Starting from base rates beats reasoning from the vivid details of your own case, which is why Flyvbjerg found cost overruns of roughly 20% on roads and 45% on rail.17 MIN5.2k