While much stratification research has focused on understanding the patterns and consequences of differentiation, previous studies have not considered similarly important variation in students' trajectories through higher education, and particularly their participation in the labor market. Results from the National Longitudinal Survey of Youth of 1997 (NLSY97) indicate that degree completion in a differentiated system of higher education is related to students' employment patterns. Students who begin their educational journeys in community colleges as well as students from less advantaged family backgrounds are more likely to dedicate longer hours to paid employment, which has negative consequences for degree attainment. Employment patterns contribute to gaps in degree completion among students from different family backgrounds and to a lesser extent to inequality in degree completion between students beginning postsecondary education in community colleges vs. 4-year institutions. A more complex set of patterns is revealed when examining the relationship between employment, family background, and degree attainment across different institutional types and educational credentials. These findings highlight the importance of developing a more comprehensive understanding of inequality in educational attainment by considering the relationship between differentiation and work.