This study examined the best practices of teachers who have been retained in the profession and also revealed the issues facing teachers who are considering leaving the profession. In addition to the potential implications for practice at other schools facing similar issues, the primary intention of this study was to discover useful and appropriate recommendations that can be applied to the school used in this study. Further, this study distinguished the needs of new teachers from more experienced teachers, to see how retention strategies should differ according to time in the profession. This study utilized a qualitative case study approach. The participants included nine teachers at various stages of their career who were employed at one urban, public middle school in Arizona. The results revealed that the teachers in the early stages were most motivated by their passion for students and were most concerned about their salary, in part because of the lack of respect it was equated with; the mid-career teachers were most concerned with the lack of parental involvement; the late stage teachers were particularly motivated by the retirement benefits in their future and focused their recommendations on things applicable to teachers early in their careers.