This paper examines the phenomenon of career transitions in terms of learning using an autoethnographic story of our own career moves. In the contemporary world of globalized flexible employment, inter-organizational career moves are increasingly prevalent and the learning associated with such transitions needs to be better understood within human resource development (HRD). We show that the learning required in career transitions extends beyond the acquisition of new knowledge and the development of new skills to the appropriation of new identities. We overview identity theorizing and, adopting a social constructionist perspective, explain the concept of identity work to understand the nature of identity learning in career transitions. We then reflexively examine our autoethnographic methodology, proceed to tell the story of our career transitions, and then interpret this story in terms of identity learning. Conclusions are drawn showing how the learning associated with career transitions involves conscious and unconscious identity work to release an established way of being, cultivate a new and desired way of being, and to cope with the existential anxieties associated with transition. Significant implications for international HRD scholarship, policy, and practice are proposed.