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This study intends to extend our understanding of Asian American college students’ transition to college. Using the Gates Millennium Scholars program surveys (n=1691), we examine how high-achieving, low-income Asian American college students’ perceptions of challenges adjusting to college and self-worth affect their academic and social engagement during their college freshman year. The causal model using the structural equation modeling technique showed that the more difficult the respondents perceived academic, social, and financial challenges at the beginning of the year, the less likely they would be engaged either academically or socially by the end of the year. This was also mediated by students’ perception of self-worth, which was consequently positively linked to their level of engagement in academic and social activities.