Understanding how individuals learn at work throughout their lives is significant for discussions of lifelong learning in the current era where changes can be unpredictable and frequent, as illustrated by the COVID-19 pandemic. Despite a corpus of literature on the subject of "learning", there is little research or theoretical understanding of "change over time" as a dimension of individual learning at work. Increasing emphasis has been put on individuals' personal development, since they play key mediating roles in organisations' work practices. This article proposes the concept of the "learning journey" to explore the relational complexity of how individuals learn at different workplace settings across their working lives. In order to illuminate this, the article draws on the learning experiences of two workers with different roles at two points in time across different workplaces. The author argues that individual learning involves a complex interaction of individual positions, identities and agency towards learning. This complexity is relational and interrelated with the workplace learning culture, which is why learning is different for individuals in different workplaces and even for the same person in the same workplace when occupying different roles.