(This study examines the directionality of the associations among cognitive assets (IQ, academic achievement), motivational beliefs (academic self-concept, task values), and educational and occupational aspirations over time from late adolescence (Grade 10) into early adulthood (5 years post high school). Participants were from a nationally representative sample of U.S. boys N = 2,213). The results suggest that (a) self-concept and intrinsic value have reciprocal effects with academic achievement and predict educational attainment, (b) self-concept is consistently found to predict occupational aspirations, (c) the associations between achievement and aspirations are partially mediated by motivational beliefs, and (d) academic self-concept in high school had stronger long-term indirect effects on future occupational aspirations and educational attainment than task values and IQ.