Youth unemployment reduces the capacity to achieve diverse markers of adulthood, potentially undermining the young adult’s sense of confidence and independence. While parents often come to the aid of their unemployed young adult children, such support may also have negative psychological repercussions. Applying a hierarchical modeling strategy to longitudinal data from the Youth Development Study, the authors find that both unemployment and parental financial support have negative consequences for youth’s self-efficacy. These common experiences may thus diminish youth’s personal psychological resources as they make the increasingly lengthy and precarious transition to adulthood.