Healing Arts and Social Change employs a critical analysis of our educational, political, and justice systems while simultaneously exploring internal landscapes. It does so while studying theories and cultivating tools for disrupting, transforming, and uplifting the political and the personal. Beyond engaging in typical critical readings and class discussions, the course also includes group meditations, “theatre of the oppressed” activities, music, movement, and shared poetry practices, thereby merging intellectual and creative explorations with intimate and embodied learning that is rare in academia and even rarer in prison. The warden and the community resource manager at the prison are kind, smart, strong African American women who hold the primary positions of power that allow us in. The author holds the multiple truths presented in this essay as one paradoxical whole: the program recognizes the beast it’s up against, and then marches on, hoping to ignite connection, critical awareness, and change, on individual and institutional levels.