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By analyzing a series of email exchanges between herself and Hip Hop Education scholars, the author, a veteran secondary educator, investigates the role of cyphers and teaming in school settings that oftentimes do not recognize or honor the labor and the brilliance of BIPOC teachers and students. Over the course of the month and a half-long exchange, the discussion moves from how the author might describe her leadership and collaborative classroom work to the realization that this work is, in fact, inexplicable. This analysis delves into the power of the cypher and pedagogies of love and joy in classrooms while also addressing the realities of this work, including the pain and ostracization that can follow when teachers enact radical teaching practices in traditional school structures. This dialogue reveals the necessity of showing up as our authentic selves in classrooms and in the academy and reminds us that true pedagogies of love and resistance start within.