Four late-career academics take a “first person” view of their careers over time, using written autobiographies. These stories were coded for common phases, themes, and tensions, retold as narratives, reimagined as metaphors, and recreated as visual stories. A brief overview of relevant career theory and identity theory is presented, and various activities undertaken during the self-discovery process are described and linked to storytelling or narrative theory. Interpretation focuses on similarities and differences in the four late academic careers and identity work during role transitions. Connections are made to career theory and identity theory. The authors believe this article might serve as a catalyst to others wondering about their careers, their identities, and future possibilities.