Individuals who choose teaching as a career face a variety of challenges. How teachers deal with these challenges can significantly affect their job satisfaction and continual pursuit of excellence. The qualitative research we are presenting summarizes factors related to reinvestment in teaching in tenured teachers who have taught at the secondary and collegiate level for at least 18 years. We conducted semi-structured individual interviews with 12 faculty from the secondary level, 11 faculty from 2 degree institutions, and 11 faculty from 3 degree institutions. We asked them questions such as what factors contribute to their success in teaching, what factors contribute to their longevity in teaching, and what challenges they have faced throughout their career. Data were audio-taped and transcribed and a content analysis was performed in an effort to discern similarities and differences between factors related to longevity in teaching at a variety of levels. Transcript data were analyzed by both presenters independently and categories were derived based on discussions and consensus building. The factors that overlapped the most between participants were those that contributed to success in teaching. These factors include potential for growth and success at work (e.g., supportive administrators and colleagues, invigorating challenges), being recognized for good teaching, the dynamic nature of health education, the realization of talent for teaching, and the autonomy and freedom in their teaching. Interestingly, the factors that contributed to their success also contributed to their longevity. It was apparent that those individuals who were successful at teaching were more likely to reinvest in their teaching. Participants faced different challenges at each level. Faculty at 3 degree institutions faced boredom and burnout as their most difficult challenges. Faculty at 2 degree institutions, which often require larger teaching loads, mentioned that changes in students were a difficult challenge. Lastly, faculty who taught at the secondary level mentioned discipline, diversity in students, and student violence as their most difficult challenges. Teachers and administrators at a variety of levels can learn from these factors that contribute to longevity in teaching. It is the hope of the presenters that individuals who attend this session will share their own experiences and tips for reinvesting in teaching.