This study examines the role of structural and agentic resources in shaping school-to-work transitions in England. We ask to what extent are young people able to steer the course of their lives despite the constraining forces of social structure, and how satisfied are they with their lives following the completion of compulsory schooling. Drawing on data from the Longitudinal Study of Young People in England we use sequence analysis of monthly activity data to identify differences in the timing and sequencing of education and employment transitions. We identified six distinct pathways, differentiating between an academic track, three pathways involving further education and training, as well as a work-focused transition and a group of young people who were over a long period not in education or training (NEET). The findings suggest that not all young people are inclined to follow an academic track and instead select into pathways involving vocational training or further education, enabling them to experience competence and life satisfaction. For others (about one in 10), however, the lack of socioeconomic and psycho-social resources is too overwhelming and they encounter long-term experience of NEET or are not able to transform their educational credentials into employment opportunities. The findings highlight that in addition to considering structural constraints it is important to conceptualise the role of the agent for a better understanding of variations in youth transitions