The present work aims to explore whether there exists a systematic frustration in terms of income expectations among those who have obtained high level of education in Italy, and if this mismatch between expected and effective incomes negatively affects their perception of happiness. We adopt a reference-dependent preferences model combined with the concept of “illusory superiority bias” to analyse data on “happiness” in Italy, provided by the biennial survey conducted by the Bank of Italy on the Italian households’ incomes and wealth between 2004 and 2014. Our results show a positive effect produced by education on incomes. High educated workers have on average higher income than other people, and this difference is statistically significant controlling for working experience and other possible confounding factors. However, the disutility resulting from the frustration of expectations produces negative effects on perceived happiness. Even though highly educated people are actually able to find better job matching in comparison to less educated workers, they are also more likely to seeing their income expectations frustrated.