The case of Sudbury education, a progressive school model that originated in the United States in 1968, demonstrates how pedagogy can be reimagined toward radically empowering children. Sudbury schools project an idealistic vision of individual self-actualization, self-directed learning, and egalitarian democratic participation in an unstructured pedagogical environment. This article draws on ethnographic narratives of students who have experienced Sudbury education to trace a more complex and contradictory reality of Sudbury socialization. Focusing on the case study of Natalie, a lifelong Sudbury student who transitioned to public school at the age of 15, what emerges is a narrative of self and society imbued with neoliberal discourses of self-motivation, entrepreneurship, and individualistic notions of success, punctuated by brief structural critiques of public schooling. The overwhelmingly individualistic consequences of Natalie's socialization, however, showcase the limits of Sudbury education to promote a collective sense of social responsibility.