In the spring of 2014, John Bragelman accepted an administrative position at a community college in Chicago. He struggled with the decision because it meant leaving the mathematics classroom, a space he calls home. As a critical educator, he had the opportunity to watch his students become critical participators in their communities, readers and writers of their world (Gutstein, 2006). He chose to transition to administration because he hoped for a similar narrative on a broader scale, impacting thousands instead of hundreds, but he worried that his values would be negatively influenced by being in a position of "power" in which he might unintentionally reify systemic oppression rather than doing his part to dismantle it. That spring, he encountered bell hooks' (1994) book "Teaching to Transgress: Education as the Practice of Freedom." In "Teaching to Transgress" there is a section where hooks presents a dialogue between herself and her writing voice. This writing style inspired the dialogue presented by Bragelman in this article--a dialogue between the mathematics educator (i.e., "John the Teacher"), and his recently adopted identity, the administrator (i.e., "John the Administrator"). After working in administration for a year, Bragelman returned to the dialogue, reflecting on the position and its power.