The purpose of this qualitative case study is to explore factors that lead to teachers remaining in the same position within a program at a suburban high school in a Midwestern state for the majority of their career despite high turnover rates in the state and within this district. This study used purposeful sampling to gain a better understanding of teacher perceptions of the factors that influenced them to remain in their current positions. The study participants were eight teachers who had taught in the orchestra program during their career, with three having recently retired. Data was primarily collected through participant interviews with the orchestra teachers. A number of prominent themes emerged from the interviews, consisting of respect, team-teaching, flexibility, freedom, support, and performing. It was uncanny how many responses from different participants were extremely similar and sometimes matched word for word. The Person-Environment Fit Theory (P-E Fit) was identified prior to conducting the study and provided a lens through which the data could be analyzed. Characteristics of the P-E Fit Theory consist of Personal (biological needs, psychological needs, values, goals, abilities, and personality) and Environmental (intrinsic rewards, extrinsic rewards, job demands, cultural values, and character of other individuals) factors. Findings show that a good fit between the person and the environment can have a positive impact on a teacher remaining in the same teaching position for a long duration. The orchestra staff confirmed that the congruence of personal and environmental factors allowed for long and fulfilling teaching careers to occur. Many of the factors were aligned so strongly that they were capable of fitting into multiple characteristic categories. Main takeaways from the study are that the fit of the team members really matters; support and autonomy for teachers from administrators is very important; support from colleagues can be a major positive; team-teaching is an extremely valuable tool to allow for continued individual growth and curricular alignment; and the informal vetting of potential future candidates greatly aides in the transition from retiring teachers to newly hired ones. Additional research could focus on other school districts and programs from other curricular areas, as well as whether hiring the most accomplished candidate versus the one that fits with the existing team the best results in the best and most stable learning environment.