Testosterone has recently been characterized as a personality variable, signifying individual differences in dominance strivings. This dissertation addresses the role testosterone plays in the environments people select. It was hypothesized that individuals high in testosterone would seek out high status positions, whereas individuals low in testosterone would be more comfortable in low status positions. This hypothesis was not confirmed. Instead, it was discovered that testosterone only exerts an effect on behavior in challenging or contentious settings. Furthermore, self-reported measures of dominance striving mediated the effects of testosterone. Specifically, when self-reported and physiological dominance were aligned, testosterone predicted behavior in a contentious setting whereas self-reported dominance predicted behavior in an agreeable setting. Individuals high in both testosterone and self-reported dominance were the only ones to rise to the challenge of contentious leadership. When self-reported and physiological dominance were in conflict, however, some participants demonstrated evidence of distress after denying a leadership opportunity, namely those individuals high in testosterone but low in self-reported dominance. The findings presented reveal evidence of the multifaceted nature of personality.