This essay examines enactments of freedom as political and creative actions. Returning to Hannah Arendt’s celebrated essay “What is Freedom?” I ask how do enactments of freedom enable creation and critique, enactments that challenge our perceived failures of world and society, but also encourage us to imagine new terms for acting in the world and for creating new worlds. In this respect, the philosophical question of freedom is also an aesthetic question: where do we locate the potentialities for new creation, which themselves might formulate new terms of political action?