Self-handicapping is an anticipatory self-protective strategy in which individuals create or claim obstacles to success prior to an important performance to excuse potential failure. The present research sought in four studies to document the anticipatory nature of self-handicapping, examining the role of prefactual (“what if …?”) thoughts in this strategy. Individuals prone to self-handicap were more likely to generate prefactuals, identifying ways to undermine their performance. Moreover, inducing individuals to consider these thoughts increased self-handicapping behavior, whereas focusing individuals on ways to improve their performance actually reduced self-handicapping behavior. Implications of this work for understanding the cognitive processes underlying self-handicapping behavior and for interventions that seek to minimize this self-defeating behavior are discussed. Copyright © 2011 John Wiley & Sons, Ltd.