This article investigated the key psychosocial factors that impact upon National Collegiate Athletic Association (NCAA) Division-1 male basketball players, as they transition from college to postcollege athletic or nonathletic careers. Participants (N = 9) were current/former NCAA Division-1 basketball players. Four participants were selected based on their current transition status and five were selected based on their previous transition success. Qualitative semistructured interviews were used to examine participants’ perceptions of current and postcollege transitions for the relevant groups. Interviews were based on the developmental model of Wylleman and Lavallee and the model of human adaptation to transition. Using grounded theory methodology, five categories were identified that relate to the transitioning process as experienced by the research sample. Research limitations and implications arising from this exploratory examination are discussed.