In this paper, the authors provide an overview of the unschooling movement, highlighting the important philosophical differences, among other differences, between unschooling and homeschooling. They then argue that to the extent that traditional schooling is a project of massification--increasingly dominated by a neoliberal ethos in our contemporary times--as opposed to emancipation, unschooling should be seen as its antithesis, providing an option for parents seeking a truly democratic education. Building on the basic presumption of the importance of autonomy, the authors contend that unschooling provides important insights to democratic education. A model that radicalizes Rousseau through Freire is presented. Specifically, the authors note Rousseau's injunction to choose between making a person or making a citizen, and then consider Rousseau's notion of the general will in combination with Freire's lesson that citizens must engage with the collective in critically transitive ways. Rousseau and Freire can be read together to present a philosophy of unschooling in schools necessary to education for democracy to overcome the massifying, neoliberal impulse of our time.