In the academy and in popular discourse, freedom is the prevailing political ideal of our age. Due to this normative and rhetorical primacy, we must continually work to understand what we mean when we say "freedom," and what implications it has for our individual and collective lives. My dissertation argues that our predominant understanding of freedom, largely derived from liberal political philosophy, is at odds with the form of life that democracy requires. I read Hannah Arendt and Michel Foucault to develop their critiques of this conception of freedom and its relevant normative framework, and place into dialogue the conceptions of political freedom legible in their work. In doing so, I contribute to the conceptual elaboration of a freedom that is experienced as political engagement.