With the aim of bridging the gap between the understanding of individual agency and that of structural constraint, this article deals with the ways in which autobiographical research can provide insight into how individuals negotiate the social contexts in which they are located. Despite the strong utilitarian discourse about the centrality of English for social and economic advancement in Hong Kong, there has been insufficient attention paid to the affective and social aspects of different study and work experiences in which differing linguistic and cultural capitals are valued. With this neglect in mind, this reported study explores how two individuals engage in self-identification and self-scrutiny in the education, legal and media fields. This is a matter of interest with regard to the power of narration in organising and representing social reality, and the relevance of self-reflexivity to the development of agency and educational capital as recorded in narratives of transition. Writing autobiographical reflections on their experiences in institutions and social relationships gave the individuals a therapeutic opportunity to formulate clearer versions of their personal history and identity in their transition to work.