This longitudinal study assessed the career aspirations and ultimate careers of 28 academically talented American girls across three time periods: Time 1 (7th/8th grade), Time 2 (11th/12th grade), and Time 3 (current study, 21 years post-Time 1). Two decades after the initial study, these participants are all in their 30s, identify as female, and were primarily employed. The women answered a battery of survey questions, and the data were analyzed through both qualitative and quantitative methods. Results clustered around three primary themes: their careers, children, and specific influences on their ultimate academic and career trajectories. Although the participants generally adhered to their early career interests, they elaborated on circumstances contributing to their success, which included parental influences on their early academic aspirations. This study offers educational and career development counseling recommendations while emphasizing the enduring impact of early career guidance and the influential role of key figures in fostering academic and vocational success.