There is a lack of longitudinal research linking adolescent career aspirations to adult outcomes other than career and income attainment. Drawing on Nurmi's (2004) and Salmela-Aro, Aunola, and Nurmi's (2007) life-span model of motivation and using quantitative survey data at ages 16, 23, 33, 42, and 50 years, combined with retrospective interview data at age 50 (collected from 25 members of a British cohort study born in 1958), we aimed to gain a more rounded understanding of the role that adolescent career aspirations play in shaping not only adult career development but also adult identities and well-being. Twenty-two of the 25 participants fulfilled their adolescent career aspirations later in life through achieving (a) the exact career they aspired to or (b) the social status of the career they aspired to. In relation to adult personal identity and well-being, the findings suggest that what matters is not just whether a person aims high at age 16 (i.e., to be a professional or a manager) but also whether the person remembers having strong or meaningful career aspirations. Further themes, gender differences, and implications for policy and future research are discussed. (Contains 4 tables.)