Challenges are a constant across all kinds of musical contexts, and teachers are always looking for ways to help students overcome them. While there are many technical and pedagogical approaches to helping students achieve in music, psychology also plays a significant role in the struggles that students face. Counteractive optimism, the act of predicting success in preparation for completing a difficult task, improves performance in the face of challenge and serves as a vehicle for the development of self-efficacy, which has a powerful direct effect on overall performance outcomes. In this article, I explain counteractive optimism and self-efficacy, their benefits, and their direct applications to music.