Building on the Wisconsin Model of Status Attainment, this study examined the contextual process of obtaining educational attainment and the subsequent work outcomes and career satisfaction. This study used the National Longitudinal Study of Adolescent Health (Add Health) with structural equation modeling techniques to assess US participants from adolescence to young adulthood (N = 8309). Socioeconomic resources provided by parents in adolescence directly predicted education outcomes and were partially mediated by family success expectations. Family success expectations were an important predictor of education outcomes. Neither socioeconomic resources nor success expectations directly predicted work outcomes or career satisfaction. Instead, education was the direct predictor of career satisfaction with work outcomes partially mediating. A multiple group analysis was conducted to compare outcomes between men and women. The discussion explores the implications of the findings and educational attainment for young adults in a global society. (Contains 3 tables and 2 figures.)