The authors focus on many of the complex issues that sport psychologists face when working with athletes through the process of leaving sport. They briefly review the literature on career termination to serve as a foundation for a discussion of the effects that an athlete’s career termination can have on teammates, family, and the self. The authors also explore the issue of bias and prejudice. People intimately involved in sport (sport psychologists included) often have a prejudice toward sport relative to other possible activities or goals. This bias might influence how sport psychologists listen to, interpret, and formulate athlete cases. Case examples are used to highlight the difficulties of identifying career-termination concerns and the professional and personal tensions that come with making sport career changes. With care, sport psychologists can manage career termination and related issues and effectively address the health and happiness of the athletes they serve.