Doctor of Philosophy / Family Studies and Human Services / Joyce Baptist / The model minority stereotype portrays Asian Americans as resilient, educationally and financially successful, and family-focused, while it downplays the realities of discrimination and its effects on self-esteem. Research suggests that gender roles and immigration experiences are contributing factors to why Asian American women, especially second-generation immigrants, experience greater stress than women of other ethnic groups and Asian American men in general. Considering most Asian Americans are of East and Southeast Asian heritages influenced by Confucian family values and gender roles, this study examined how these values mediated the associated from discrimination to self-esteem during adolescence, and to educational and financial achievement (wellbeing) during adulthood for second-generation immigrants. Using data from the Children of Immigrants Longitudinal Study (N = 554), results from a partially constrained group-comparison model demonstrated that Confucian values of familism and family cohesion were factors that significantly predicted adolescent self-esteem and adult educational achievement. Men’s level of familism endorsement was also uniquely related to experiences with discrimination. Clinical implications and further research directions are discussed.