The purpose of this study was to examine the career experiences of three music teachers through the lens of expertise theory. An additional purpose was to discover how the participants viewed success in the field of music education. Using an instrumental case study design, three experienced music teachers--who served as the case--were interviewed about these topics. Expertise theory, as well as the concept of grit, provided the theoretical framework for this project. Through a multi-level process of coding, several themes were derived from the interview transcripts. Themes included common early career struggles and perseverance through a reliance on mentors, a focus on problem solving, and adapting to new and challenging experiences. In addition, participants defined success as being student-centered at all times and maintaining program enrollment. Finally, the participants seemed to embody the last phase of expertise theory by being innovators in their field. Implications for music teacher preparation programs, pre-service music teachers, and inservice teachers are discussed.