This article discusses the career biographies of four individuals in transition. They were responding to the challenges of engaging in work-related learning, re-shaping their careers and their career identities. The four cases were selected from a larger sample of fifty participants in a five-year longitudinal, qualitative case study, which has evaluated the effectiveness of career guidance and counselling in supporting the career transition and development of adults in England. They have been chosen because they illuminate different patterns of responses associated with career change. In particular, they demonstrate the value of education-based or work-based learning in helping individuals not only update their skills, knowledge and competences but also to keep a positive disposition towards learning. Whilst access to opportunities for learning and development is important, it is also clear that some individuals are much more pro-active than others in taking advantage of opportunities. In contrast, others perceive themselves to be more constrained by circumstances, which can lead to disengagement from learning and development. Reshaping careers, learning and identities is a daunting challenge for individuals and career guidance and counselling can play a role in facilitating attempts to construct a new coherent career narrative that help drive these processes.