As schooling becomes increasingly regulated, we often hear complaints to the effect that if only students and teachers had fewer constraints and requirements, they would be free to learn and to teach. In this thesis, I revisit an educational movement that attempted to abolish all constraints on children and students: libertarian educational theory. I consider the strengths and weaknesses of the libertarian approaches to education that were voiced in the 1960s and '70s, focusing on the writings of three representative libertarian educators: A. S. Neill, John Holt, and Ivan Illich. I then reframe the question of children's freedom in a non-dichotomous way by proposing that we think of freedom as agency-within-structure. This modified conception of freedom helps us recognize that freedom is not the mere absence of constraints, and in fact certain constraints are actually necessary to promote freedom. I argue that requiring all children to learn to read is just such a constraint, because in our society it is a prerequisite for the possibility of self-directed education. At the same time, even if it is not possible for all areas of learning to be optional, we can still teach those that are required in a way that is consistent with the goals of libertarian education. I close by exploring practical principles for a libertarian pedagogy of reading.
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