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Although regarded colloquially as a route to upward social mobility, numerous sociological investigations reveal that educational institutions contribute to the reproduction of class status—and pathways to medical training are no exception. This paper extends research on horizontal stratification processes by examining how class background shapes students’ experiences with the medical school application process, viewed through the lens of college employment experiences. Drawing on life history interviews with 43 premedical students from the United States, we identify how the economic capital available to these students shaped their perspectives on paid employment, how those perspectives influenced labor opportunity, and how students drew on work experiences to prepare their medical school applications. We characterize two approaches to paid employment, self-cultivation and financial sustainability, linking them to students’ family backgrounds. Our findings contribute to recent efforts in medical sociology to understand medical career trajectories by characterizing how social inequalities shape pathways into medicine.