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Increasing numbers of college graduates are returning to higher education by enrolling in graduate degree programs (NCES 2022). This is related to a broader trend across cohorts of an increasingly complex and less predictable unfolding of life course events (Boissonneault 2021; Furstenberg 2010; Grodsky et al. 2021). Among college graduates who re-enroll in graduate study, the majority have at least one spell of full-time employment between college graduation and re-enrollment. College graduates’ first jobs post-graduation may be a crucial gateways to career pathways (Moss-Pech 2025; Streib 2023). Recent evidence demonstrates the importance match between an individual’s educational credentials and occupation for earnings (Bol et al. 2019; Odle and Russell 2024; Witteveen and Attewell 2024). A recent study showed that mismatch between undergraduate degrees and their first job explained nearly two thirds of socioeconomic (background) earnings inequality among college graduates (Scott-Clayton et al. 2025). However, we know little about how the graduate degrees intervene in these relationships, or the longer-term reverberations of early employment mismatch. Given this, I ask how two characteristics of students’ first post college jobs – match with their BA field and their graduate field – are associated with graduate enrollment in the first four years following college, earnings 10 years after college and occupational status 10 years after college across four cohorts of college graduates from the 1980s-2010s. I find that first jobs matching one’s BA field are associated with lower likelihood of graduate enrollment, and have no association with later earnings net of controls. These results are consistent across cohorts. However, I find a changing relationship between graduate field matching to work and bachelor’s degrees and earnings across cohorts.