An individual's capacity to be effective throughout their working life is now claimed to be necessary to sustain individual, local and national well-being. Yet without knowing more about an individual's motivations to continually learn throughout their working life, it remains uncertain how realistic these expectations are. This paper examines the transitions and continuities in a year in the working lives of five individuals. It illuminates how their identities, subjectivities and sense of selves are exercised through the churning and transformations that comprise their working lives. Although accepting the intertwining between the individual and social, the primary focus here is on individuals and their sense of self. Against some predictions, the five individuals were able to enact their working lives in ways that broadly served their personal interests and goals, even to their detriment. This included achieving continuities associated with their sense of self in negotiating transformational workplace requirements. These findings from just five workers prompt consideration of a more relational basis for conceptualizing learning throughout the working life and the role of the self in that process. It suggests that learning throughout life is aligned with the personal as much as the social suggestion of the workplace, employers or government and that external mandates and regulatory practices may be insufficient and ineffective in securing lifelong learning goals. Copyright © 2005 Taylor & Francis Ltd.