The association between education and subjective well-being has long been investigated by social scientists. However, prior studies have paid inadequate attention to the influence of societal-level educational expansion and skills diffusion. In this article, multilevel regression analyses, using internationally comparable data for over 48,000 individuals in 24 countries, detect the overall positive linkage between educational attainment and life satisfaction. Nevertheless, this relationship is undermined due to the larger degree of skills diffusion at the societal level, and no longer confirmed once labor market outcomes are accounted for. Meanwhile, the extent of skills diffusion per se is positively and substantially associated with people’s subjective well-being even after adjusting for key individual-level and country-level predictors, whereas other societal conditions including GDP, Gini coefficients, safety, civic engagement, and educational expansion do not indicate significant links with life satisfaction in the current analysis. Given that recent research suggests skills diffusion promotes the formation of meritocratic social systems, one may argue it is the process of fairer rewards allocation underpinned by skills diffusion, rather than the status quo of macroeconomy, economic inequality, social stability, and educational opportunities as such, that matters more to people’s subjective well-being.