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Decision-making paradoxes

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Monty Hall problem
mathematical problem
Buridan's ass
philosophical paradox regarding free will
paradox of tolerance
logical paradox in decision-making theory
Arrow's impossibility theorem
Result that no ranked-choice system is spoilerproof
St. Petersburg paradox
paradox involving a game with repeated coin flipping
voting paradox (Condorcet)
Marquis de Condorcet's observation regarding times when voters' collective preferences are cyclic, even when voters' individual preferences are not
Abilene paradox
social phenomenon in which a group of people collectively decide on a course of action that is counter to the preferences of many or all of the individuals in the group
Newcomb's problem
thought experiment about a game involving a reliable predictor of the player’s actions
Allais paradox
apparent violation of the predictions of expected utility theory
two envelopes problem
brain teaser, puzzle, or paradox in logic, probability, and recreational mathematics
Ellsberg paradox
paradox in decision theory
Parrondo's paradox
paradox in game theory in which a combination of losing strategies becomes a winning strategy
Three Prisoners problem
mathematical problem
Green paradox
book by economist Hans-Werner Sinn
Inventor's paradox
Solving a problem by solving a larger problem
Downs' paradox of voting
the paradox that larger the electorate, the less each vote matters
Morton's fork
false dilemma in which contradictory observations lead to the same conclusion
Prevention paradox
situation where the majority of cases of a disease come from a population at low risk
disposition effect
selling of assets that have increased in value, while keeping assets that have dropped in value
hard–easy effect
cognitive bias relating to mis-estimating success based on perceived difficulty
Pascal's mugging
philosophical thought experiment: “A mugger, who forgot his weapon, proposes a deal to Pascal: ‘you give me your wallet, and I will give you N times the money, where N is large enough to compensate for the low probability of me honoring the deal’”
chain store paradox
apparent game theory paradox involving the chain store game, where a "deterrence strategy" appears optimal instead of the backward induction strategy of standard game theory reasoning