The practices of parenting and educating children shape the possibilities of freedom across generations, particularly within societies marked by political constraint, social expectation, and economic disparity. Drawing on Lea Ypi’s Free, Educated by Tara Westover, and Florence Kelley’s Some Ethical Gains, this project investigates how children challenge or adopt inherited practices of inequality and investment in existing social structures. It examines parental authority versus childhood agency, questioning whether raising “good citizens” fosters autonomy or simply maintains constraint until adulthood. By examining the Albanian Communist Regime, fundamentalist Mormon communities, and the U.S. Progressive Era, this research contends that freedom is not merely a political ideal but a cultivated social practice. In unfree societies, practicing freedom can sustain survival but it can also sustain unfreedom as a political ideal. Parents shape how freedom is practiced through social belonging. In this project, I want to explore the political ramifications of this practice.