In this article I argue that the work of Friedrich Nietzsche, Gloria Anzaldúa, and María Lugones can, taken together, offer a rich and innovative approach to understanding and realizing the possibility of revolution. From radically opposed perspectives, both Nietzsche and Anzaldúa articulate the necessity of accepting contradiction and multiplicity as the conditions of political transformation, and offer a new conception of revolution that displaces mere reversal as its dominant meaning. Lugones supplies important tactical strategies for realizing this revolution in her suggestions of playful “world”-travel. Taken together, these three thinkers challenge radical critics to re-think not only the revolutionary project itself, but also their own position with regard to that project, and to the dominant order they seek to overturn.