Transition from professional football life has important implications for the health and well-being of former National Football League (NFL) players. The study purpose was to examine former NFL players’ experiences of transitioning from sport including factors that helped and factors that made transition difficult. This study used a convenience sample of former NFL players drawn from a larger study of health and function. Participants included 1,784 former NFL players, mean age = 52.3 ± 16.3 years, 59% White, and a discontinuation mean of 24.0 ± 15.6 years after leaving the league. Participants responded to open-ended transition questions via mail or electronic questionnaire with responses analyzed using conceptual content analysis. The most frequently reported factors that helped transition included career transition plan/options (48%) and social support (40%). Whereas, structure- (33%) and identity-related (23%) difficulties were reported as factors that made transition difficult. Findings identify areas for targeted interventions to enhance NFL player well-being during transition from sport.