A longitudinal perspective was taken to investigate the predictive validity of teenage job aspirations, and the relative impact of individual and contextual factors on the formulation and realisation of career aspirations at age 16. The follow-up study of a nationally representative cohort of 7649 individuals born in the United Kingdom showed that teenage job aspirations predict specific occupational attainments in adulthood. Job aspirations expressed in adolescence differed between the sexes, and were related to parental education, teacher-ratings and self-ratings of ability, test scores in mathematics, and the school environment. Occupational attainment at age 33 was significantly related to the job aspirations expressed at age 16, but also to the belief in one’s own ability, mathematical test performance, specific personality characteristics, as well as social background and gender. It is concluded that for the understanding of occupational development across the lifespan both individual and contextual factors have to be considered.