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When students expect college education unnecessary for their expected occupations, do they suffer from poorer outcomes? The question is central to college-for-all debate, but the answer remains inconclusive and focuses on outcomes in early adulthood. This study contributes to the literature by (1) analyzing the long-term effect of expectations on occupational attainment, (2) taking educational upgrading of occupation into account, and (3) connecting the debate to broader discussions on college wage premium and limited learning in colleges. Drawing from the midlife follow-up of the senior cohort in High School and Beyond (HS&B) study, I show that low educational expectation during adolescence, not incongruent expectations, is harmful to occupational attainment in midlife. Among seniors who expect going to colleges, the midlife occupational attainments are similar between those expecting upgraded occupations and those expecting college occupations. Consistent with literature on the college wage premium, the premium remains high after controlling for skills possessed, course intensity, and demographic covariates. But the extent to which college degree attainment can explain the effect of expectations depends on the timing of attainment. By showing the long-term effect of college-for-all ethos, with special attention to compositional change in occupations over time, this study provides insights to future research on more recent policies such as “algebra for all” and “computer science for all”.