The rise and decline of the Italian economy over the past 60 years form a surprisingly regular parabola, if the main European partner economies are taken as benchmark, so that its vertex equal to 1 means that Italy completely caught-up Europe around the 1990s. This implies that, in order to repeat that experience of catching-up, Italy needs to grow at extraordinary rates, which are not on the horizon. The paper shows that the Italians’ morale is even in worse conditions and explores why. The analysis firstly focuses on subjective well-being (and other subjective indices), thus finding another parabola and with more worrying features than the economic parabola. Then it explores the role of education in shaping the long-run dynamics of both the economy and subjective well-being. As a first result, the paradox of the excess supply of educated workers in Italy becomes clearer. The second result shows how poor education weakened Italians’ ability to fully enjoy their income, in particular after the shocks of the 1990s. An education policy thus becomes urgent to provide both specialized skills for production and general skills for people’s lives, thus definitively reinforcing the recent weak rebound in educational levels.