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An increasingly rich body of literature informs the field regarding the teacher labor force. Teachers are increasingly diverse with regard to both race and gender (National Center for Education Statistics, 1999), and move from instructional to administrative positions in fairly regular, predictable patterns. The career pathways of administrators and aspiring leaders are less well known. Likewise, questions continue to emerge about the ways in which schools and districts cultivate and sustain diversity in their leadership—with varying success. This paper contributes to a burgeoning literature that focuses specifically on career pathways once candidates have entered into the school leadership pipeline.