This study seeks to deepen our understanding of the factors that explain individuals’ willingness to self-censor (WtSC)—the proclivity to withhold an opinion from an audience perceived to disagree with that opinion. It does so by testing the “impressionable years” hypothesis, which states that the historical context experienced between the age of 18 and 25 years has a lasting effect on individual dispositions such as WtSC. The study was conducted in Chile, an ideal case to explore possible cohort effects because of the profound political changes experienced there in the past 50 years. Analysis of an original cross-sectional survey shows that—as expected—people who came of age in periods of political repression exhibit significantly higher levels of WtSC later in life compared with those who grew up during less repressive times.