In this latest continuation of our multipart symposium on teacher leadership, we examine what happens when self-defined teacher leaders become school administrators. Do teacher leaders who become administrators maintain a teacher identity? Can they remain committed to their vision of teacher leadership when they take on the normative requirements and responsibilities of school administration? Through a conversation with three teachers leaders, we explore the rewards and trials of teaching, the choice to become teacher leaders and then administrators, and the unique challenges that face administrators who deeply value the professional, political, and collaborative work of teachers. [For Part 1 of the symposium, see EJ1110798 and for Part 2 see EJ1117589.]