The experiences of women while aspiring to, attaining, and retaining executive roles as leaders in education vary significantly from the parallel journeys of men aspiring to the same executive roles (Brunner & Kim, 2010; Odell, 2020; Pernambuco-Wise, 2011; Richards, 2023; Robinson, 2013). Dr. Tekawitha Pernambuco-Wise (2014) listed three essential doors that block the leadership path of women in independent schools: unspoken biases, risky candidates, and loneliness (pp. 2-4). To assuage these barriers, Dr. Jessica Flaxman (2022) presented leadership skills that are essential for female heads of school: the traditional critical leadership literacies and the developing and nuanced emergent leadership literacies. Specifically, the work of these two researchers can be studied and followed in women-to-women, female head of school to aspiring female head of school relationships because women must approach leadership candidacy differently than do men (Brunner & Kim, 2010).