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The first chapter uses in-depth interviews with 61 junior and senior high school girls to show how social class shapes educational and occupational aspirations and plans through the availability and use of social networks. These interviews reveal that middle class adolescents are embedded in resource-rich social networks that facilitate high educational and occupational attainment while limited social ties, family instability, and parental disengagement produce disadvantages for working class and poor youth. The second chapter uses survey data from the National Longitudinal Study of Youth 1979 (NLSY79) and National Educational Longitudinal Study (NELS) to explore the relationship between events in the transition to adulthood and fulfillment of one's educational and occupational expectations. Findings reveal that the order and timing of family formation and dissolution events can disrupt young people's paths to attainment in early adulthood. The final chapter uses NLSY79 and NELS datasets to test the relationship between falling short of one's expectations and emotional and psychological outcomes in early adulthood. Results indicate that occupational expectations can serve as baseline standard with which to judge later accomplishments--falling short of these goals leads to lower emotional and psychological well-being in adulthood. These findings support the claims of relative deprivation theory, which argues that dissatisfaction arises from the gap between what one has and what one wants.