ABSTRACT Successful self-regulation is defined as the willingness to exert effort toward one's most important goals, while taking setbacks and failures as opportunities to learn, identify weaknesses and address them, and develop new strategies toward achieving those goals. Contingencies of self-worth can facilitate self-regulation because people are highly motivated to succeed and avoid failure in domains of contingency. However, because boosts in self-esteem are pleasurable and drops in self-esteem are painful, protection, maintenance, and enhancement of self-esteem can become the overriding goal. Several pitfalls for self-regulation can result, especially when tasks are difficult and failure is likely. In this article, we describe a program of research examining these self-regulation pitfalls associated with contingent self-worth and suggest that learning orientations, particularly the willingness to embrace failure for the learning it affords, foster successful self-regulation even in people with highly contingent self-esteem.