Private sector managers’ pathways through late career and retirement are important, but insufficiently studied. Based on a large qualitative study of retiring managers in big Canadian firms, this article explores the relationships between managers’ work during their careers, their retirement transitions and their retirement activities. Three distinctive patterns of managerial work and careers are found: those of expert managers, organization managers and strategic managers. They are strongly related to how managers end their ‘full commitment’ careers and then build retirement lives by combining leisure activities, family commitments, civic involvement and paid work. Variations in retirement pathways are not well predicted by either individualization theory or theories based on generational or class habitus. Managers appear to develop distinctive orientations to acting with agency that arise from the way managerial work is organized; and these frame managers’ retirement pathways. These findings may indicate why individualization does not necessarily lead to life course destandardization.