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The purpose of our heuristic qualitative study was to explore the journey for aspiring women school leaders through the administrative pipeline. Through the lenses of gender performance and role congruence, we illuminated the transformation of our participants' professional aspirations throughout and following the administrative certification process and during employment. As a result of our analysis, a heuristic was defined, framing how women vacillate between empowerment and complacency in their career trajectory, often dependent upon a "necessary clause" to engage in professional change. The research has several important implications for administrative preparation programs and for aspiring leaders