In this paper we examine the associations between gender, family background, general cognitive ability (g), teenage career aspirations, and career attainment in mid adulthood drawing on two large representative samples of the British population born in 1958 (N = 6,474) and in 1970 (N = 5,081). A developmental-contextual model of career development is tested, using Structural Equation Modelling to map the pathways linking early experiences to adult outcomes. Results show that in both cohorts career aspirations measured at age 16 predict career attainment of cohort members in their mid 30s, even after controlling for family social background and general cognitive ability. Compared to their less ambitious peers, those with aspirations for a professional job are more likely to participate in further education, and are more likely to achieve a professional career in their adult years. Regarding gender differences in career pathways, the findings suggest that women are more ambitious in their occupational aspirations than men and more likely to participate in further education. However, despite reducing gender inequalities in attainment, social inequalities in educational and occupational opportunities remain.