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The alignment of students’ educational expectations and occupational aspirations has been shown to be related to positive wage outcomes during the early career. However, mid-career wages are a better indicator of lifetime earnings. We use data from the National Longitudinal Survey of Youth of 1979 to examine the relationship between alignment of expectations and labor market outcomes into workers’ late forties. We show that the effects of misaligned expectations on labor market outcomes change over years, indicating that having high and aligned expectations are even more important for labor market outcomes than previously estimated. Differences in the relationships by subgroup indicate the need for tailoring interventions to the particular needs of students.