This piece explores questions of power, conflict, and community in education through a story of Chicago educators engaging in experiential inquiry processes. One of these processes is a "Theatre of the Oppressed" exercise for dealing with conflict in education settings. The other process described here focuses on a text that emerged from and describes conflict in education. This text is a little-known manifesto of progressive education written in Chicago in 1900 that denounces the school system's disempowerment of teachers, their experiences, and their voices. This text, written by feminist educator Ella Flagg Young, offers an important corrective to progressive education literature by foregrounding the issue of power imbalance in education. By describing the educators' "Theatre of the Oppressed" process next to their reading of Young's "Isolation in the Schools," I seek to further discussion of power in education settings. I argue that group inquiry processes that facilitate analysis of power, as it operates both in interpersonal life and in systemic structures, embody the kind of power that Young sought for educators to create and sustain in the face of an education system dominated by wealthy white males.