What is teacher self-knowledge? What does it have to do with biography and our willingness or ability to change? As categories collapse around us, we can scarcely invoke the Socratic injunction “know thyself” without at the same time embracing a life of confusion and contradiction. In this article, I call upon a philosophical stance that is purposefully unfinished, fractured, and fracturing. As the pieces of my life conjoin with yours, I am able—if I so choose—to see the world as if it might be otherwise. Should teachers take up such a posture, we might better understand the contradictions that our students experience as they move between categories, testing and refusing identities. Using assemblage or bricolage as my method, I examine not only the contradictions of my own history as a “failed and not-failing” gay educator, but mixing my stories with others I reflect upon the simple notion that identity claims are less important than the time we spend between these claims. Embracing a life that prolongs these confusions is the path (I think) toward self-transformation.