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In this paper, based on a qualitative longitudinal study of 100 students as they transition from college into the labor market, I examine the ways in which family background and university institutional processes interact in guiding student post-graduation pathways. While the quantitative literature poses conflicting findings on the degree to which college is a “great equalizer”, the qualitative literature shows key differences in experience in college by class and race/ethnicity. I show linkages between these experiences in college and later experiences with both job search and experiences on the job. Despite strong messaging and invitations from the university, continuing-generation students often find it difficult to reject parental expectation and influence while first-generation students often lack the resources to take advantage of university-based opportunities. While universities have made important advances in supporting equal access to successful careers, family background forces are difficult to overcome for both first-generation and continuing-generation students.