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Adolescence is a highly formative period in the life course for shaping future trajectories; a large body of research has demonstrated that achievement orientations, like educational aspirations and plans, predict adult attainments. However, there has been little systematic study of the long-term impact of other forms of motivation or whether the importance of these psychological traits is moderated by one’s available alternate resources. This study examined whether personal motivation serves as a resource substitute for parental education in achieving upward educational mobility and whether this effect is moderate by gender. Using data from the longitudinal Youth Development Study, I estimated the effect of multiple forms of adolescent motivation on odds of college completion among youth whose parents did not earn a bachelor’s degree. Controlling race, gender, family structure, parental income, and parental educational expectations, several achievement orientations predicted upward mobility: academic self-concept, educational plans, optimism about the future, and mastery. Although, women’s achievement depended more on these motivators than men’s. These results suggest that adolescent motivation may compensate for parental education in attaining higher education, particularly for women, indicating the power of motivation to enable “doing better than expected” in the United States.