Drawing on data collected from two longitudinal Cohort Studies following the lives of over 20,000 individuals born in the United Kingdom 12 years apart in 1958 and 1970, respectively, this paper examines antecedents and outcomes of educational and occupational aspirations of young men and women, covering the transition from dependent childhood into independent adulthood. Two analytical models, a Social Reproduction Model and a Developmental-Contextual Model are tested to assess the processes by which family background and the wider socio-historical context influence work and family related careers. The findings demonstrate the persistent role of gender, social origin and individual agency processes as well as the influence of a changing socio-historical context on career development. Results are interpreted with regard to biographical agency processes linking individual lives with social contexts across the life course.