There has been a great deal of scholarly interest in trying to uncover the factors that account for variation in educational attainment. Equally important, but not yet fully answered, is why some people aspire for high levels of education and others do not and, moreover, why some people believe that they will reach their educational aspirations and others do not have much optimism. The current study sought to address this gap in the literature by examining whether socialization factors and individual differences account for why some people reach their desired level of education and why some people believe that they will reach their desired level of education while others do not hold such beliefs. To do so, data drawn from the National Longitudinal Study of Adolescent to Adult Health were analyzed. We examined four outcome measures related to whether the participant earned their desired level of education and whether the participant believed that they would achieve their desired level of education if they had not already. Each of these models was estimated for the full sample and separately for males and females. The results revealed that neighborhood disadvantage was associated with achieving the desired level of education in some of the models for the full sample as well as separately for males and females. In addition, intelligence, low self-control, and delinquency were consistently related to reaching the desired level of education in the full sample and for females, but not males.