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Men today are less likely to enroll in postsecondary education and complete a degree compared to women. One prevailing theory is that men do not view college as necessary for their careers and that entering the workforce directly after high school is a better bet for economic security. However, there is limited research on how men arrive at this conclusion, evaluate their options, and how these calculations have changed over cohorts. Using life history interviews from two cohorts, 1978 and 1992, we analyze how men develop aspirations and how they assess their options. One strength of the cohort design is that these cohorts bookend important shifts in the education and labor market landscape. The 1978 cohort came of age around when women first started to obtain more bachelor’s degrees. The 1992 cohort came of age during labor market restructuring. Our participants come from two sites with lower educational attainment than the U.S. average. This provides a novel opportunity to learn from men who do not enroll in postsecondary education and those who do not complete bachelor’s degrees. For the 1978 cohort, aspirations are shaped by close community ties like immediate and extended family, neighbors, and friends. These connections expose the older cohort of men to careers in the trades long before high school graduation. These job experiences inform men’s aspirations, setting them up for successful careers that do not require a college degree. The older cohort men rarely felt the need to attend college. However, men in the 1992 cohort do not describe networks as rich in opportunities and do not have access to stable careers. The younger cohort are more likely to pursue low-wage work long-term. They are less likely to attend college because they do not believe it will help them get ahead in that line of work.