CEO retirement represents the most common reason for executive succession in the United States and globally, with important implications for many stakeholders. Yet a comprehensive theory of late-career-stage executives—such as those approaching retirement—is absent from the management literature. Building on the literature on liminality, we develop theory centered on late-stage CEOs by conceptualizing executive retirement as a process that unfolds in three phases. In our framework we integrate upper echelons theory with regulatory focus theory to examine the relationship of promotion and prevention focus with the timing, pace, and nature of retiring executive role separation, transition, and reincorporation. We then construct four CEO ideal types—icon, custodian, balancer, and chairwarmer—which are based on configurations of the orthogonal dimensions of promotion and prevention focus, and by following each type along a unique pathway, we show how an integrated view of these dimensions leads to nuanced predictions. Finally, we highlight the dynamic nature of our model by investigating the role of two salient contextual factors—CEO age and past achievements—and show how they can alter retirement pathways. We discuss how a deeper understanding of executive retirement informs strategic leadership research.