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We present evidence of sudden-death aversion (SDA)—the tendency to avoid “fast” strategies that provide a greater chance of success, but include the possibility of immediate defeat, in favor of “slow” strategies that reduce the possibility of losing quickly, but have lower odds of ultimate success. Using a combination of archival analyses and controlled experiments, we explore the psychology behind SDA. First, we provide evidence for SDA and its cost to decision makers by tabulating how often NFL teams send games into overtime by kicking an extra point rather than going for the 2-point conversion (Study 1) and how often NBA teams attempt potentially game-tying 2-point shots rather than potentially game-winning 3-pointers (Study 2). To confirm that SDA is not limited to sports, we demonstrate SDA in a military scenario (Study 3). We then explore two mechanisms that contribute to SDA: myopic loss aversion and concerns about “tempting fate.” Studies 4 and 5 show that SDA is due, in part, to myopic loss aversion, such that decision makers narrow the decision frame, paying attention to the prospect of immediate loss with the “fast” strategy, but not the downstream consequences of the “slow” strategy. Study 6 finds that people are more pessimistic about a risky strategy that needn’t be pursued (opting for sudden death) than the same strategy that must be pursued. We end by discussing how these twin mechanisms lead to differential expectations of blame from the self and others, and how SDA influences decisions in several different walks of life.