Athletic retirement is a significant life transition with potentially deleterious effects on former athletes’ social, mental, and physical health. Individuals with high athletic identification are particularly susceptible to unhealthy eating and exercise behaviors, yet self-compassion may guide more adaptive transitions by supporting positive identity adaptation and healthier eating and exercise behaviors. The purpose of this study was to explore how student-athletes experience retirement, specifically their navigation of personal diet and exercise routines post-sport, and how self-compassion may shape this process. Seven collegiate athletes of high athletic identification completed one semi-structured interview two months following the end of their athletic careers. Interview questions developed from Taylor and Olgivie’s 1994 athletic retirement model and Neff’s 2003 self-compassion scale probed athletes’ diet, exercise, and self-compassion practices. Interpretative phenomenological analysis, bolstered by reflexive journaling and critical friend consultation, identified individual themes before considering themes across participants. Results indicated athletes largely accepted retirement, although often extended their transition from sport by resisting change. Mixed self-compassion tendencies and volatile exercise motivation were seen within and between participants, and a heightened and uncomfortable sensitivity to eating habits and bodily changes was consistent among athletes. This study contributes to a larger three-part study considering eating, exercise, and self-compassion throughout athletic retirement, supplementing scarce longitudinal research into athletic retirement, and pioneering self-compassion in retirement literature. Significantly, this study provides rare real-time insight into retiring athletes’ thoughts, feelings, and behaviors at an acute retirement phase, suggesting athletes may benefit from greater guidance as they enter a foreign life outside sport.