Scholars of democratization have sought to understand two patterns: the observed correlation between income and democracy, and the clustering of democratization events. We develop and estimate a model of learning that explains both patterns. In our model, countries’ own and neighbors’ past experiences shape elites’ beliefs about the effects of democracy on economic growth and their likelihood of retaining power. These beliefs influence the choice to transition into or out of democracy. We show that learning from past experiences is crucial to explaining observed transitions since the mid-twentieth century. Moreover, our model predicts reversals to authoritarianism if the world were hit with a shock to growth the size of the Great Depression.