Little work on the significance and implications of decision-making has been undertaken since that led by Hodkinson in the 1990s, and the experiences of young people on vocational programmes and their reasons for undertaking them remain under-theorised and poorly understood. Drawing on two narratives from a study exploring young people’s motivations for undertaking vocational programmes, this article explores the relationship between their positioning in fields and career decision-making. The article argues that social positioning is significant in its relationship to decision-making, to the way in which young people perceive and construct their careers and to the influence of serendipity on their transitions. Drawing on a range of international studies, the article explores the implications of these findings in terms of young people’s future engagement with the global labour market, giving consideration to (dissonant) perceptions of vocational education and training as contributing to economic growth whilst addressing issues of social exclusion and promoting social justice.