A paradox exists in modern schooling: students are simultaneously more positive about the future and more depressed than ever. We suggest that these two phenomena may be linked. Two studies demonstrated that students are more likely to be depressed when educational aspirations exceed expectations. In Study 1 (N = 85) aspiring to a thesis grade higher than one expected predicted greater depression at the beginning and end of the academic year. In Study 2 (N = 2820) aspiring to a level of education (e.g., attending college) higher than one expected to achieve predicted greater depression cross-sectionally and five years later. In both cases the negative effects of aspiring high while expecting low persisted even after controlling for whether or not students achieved their educational aspirations. These findings highlight the danger of teaching students to aspire higher without also investing time and money to ensure that students can reasonably expect to achieve their educational goals.