Objective Educational and occupational ambitions are on the rise for adolescents in the United States and there is a national push for more postsecondary education. However, most young adults do not hold bachelor's degrees and many jobs do not require them. The objectives of this study were to focus on the need for aligned expectations and the longitudinal effect on educational attainment, personal income, and underemployment. Methods The methods used the National Education Longitudinal Study of 1988 (NELS:88) to examine how aligned expectations in 12th grade predict educational attainment, income, and underemployment at age 26. Results Results suggest aligned expectations in adolescence are predictive of educational attainment. Contrary to authors’ hypotheses, aligned expectations do not influence personal income or underemployment. Gender analyses revealed differences in the importance of aligned expectations. Conclusion In conclusion, the alignment process during high school will be important for future research focused on postsecondary educational goals.