The school-to-work transition presents a substantial regulatory challenge for youth in modern societies. Based on the action-phase model of developmental regulation, we investigated the effects of goal engagement on transition outcomes in a high-density longitudinal study of noncollege-bound German adolescents (N=362). Career-related goal engagement was important for attaining a desired career goal (i.e., apprenticeship) for girls who generally faced unfavorable employment opportunities. For boys, goal engagement did not predict the attainment of an apprenticeship. Goal engagement was nonetheless beneficial for well-being, predicting positive affect for both girls and boys. This effect was not mediated by attainment of an apprenticeship. The findings elucidate the role of goal engagement under structural and temporal constraints and suggest possible avenues for intervention.