In this paper, I address a perceived gap in the lifelong learning literature. There is very little research which addresses how learning should be construed, when individuals transition across a longitudinal span of their working life. This transition which could be viewed as a process of "becoming somebody", often oversimplifies the full complexity of individuals' learning experiences. Using a sociocultural perspective, the paper explores the lived experiences of individuals in the process of becoming a vocational teacher, in order to help conceptualise the individuals' learning through their working life. The study draws upon data from a completed research on a group of vocational education trainee teachers learning to teach. This paper argues that learning varies significantly from individual to individual, time to time, context to context and also in different stages of individuals' lives. This transition could be viewed as an individual learning journey, through understanding the interrelationship between individuals and the contexts, across the individuals' lives. Drawing from this understanding, the individual's agency is presented as a way that individuals construct their own lifecourse through the actions and choices they made within the opportunities and constraints of the context. The findings of the study also contribute to the understanding of changes, from the individual learner's perspective, which could be useful for policy and practice relating to lifelong learning.