The demands of Olympic-level sport create a unique array of factors that can influence athlete well-being. This qualitative study examined the perceptions of Canadian Olympians in relation to factors they believe contributed to, or impaired, their well-being over the course of their sport careers. Twelve recently retired Canadian Olympic athletes from a variety of winter and summer sports participated in the study. Participants were categorized as recently retired if they competed at one or more Olympic Games since 2010. For the study, Olympians participated in individual semistructured interviews, each of which was transcribed verbatim and subject to thematic analysis. An interpretivist approach underpinned this study. The results included nine lower order themes that were subsumed within three higher order themes. These included interpersonal (i.e., coach athlete relations, support team, training environment), national sport federation (NSF) operations (i.e., finances, planning, communication), and intra-individual (i.e., resultsfocused mindset, identification with elite sport norms, feelings of isolation vs. connectivity) factors that participants felt contributed to, or undermined, their well-being during their elite sport careers. When taken together, the results of this study point to the complexity of factors that potentially influence Olympic-level athlete well-being as well as unique insights from Olympic athletes into interpersonal, NSF operations, and intraindividual factors that are worthy of more scrutinized investigation. Implications for future research and applied practice are discussed.