For individuals with strong work identities, the decision to retire can be particularly challenging. For academic physicians, retirement is an important personal decision that also has far-reaching implications for the healthcare system. This is because academic physicians are responsible for producing the research from which key medical decisions are made, for training future healthcare providers, and for providing specialized care for patients. For this study, we conducted focus groups with academic physicians from a large research university in Canada and then performed inductive thematic analyses to examine perceptions and concerns about later life career transitions. This study highlights tensions between professional experiences for the next generation of physicians and individual struggles with personal identity. Findings suggest improvements to institutional programs that support flexible, agentive, and respectful retirement transitions will not only be beneficial but necessary as medical and university systems continue to grapple with issues of balanced recruitment and succession.