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Employing a feminist perspective, this paper explores how gender plays a complex role in shaping the relationship between particular women and educational leadership. This study includes the voices of 10 current and aspiring female educational administrators. Semistructured interviews and Likert scale surveys were administered and primary in the data collection. Findings of this study reveal four key themes: (1) intersection of work and family; (2) mentoring opportunities and access to resources; (3) women’s work relationships; and (4) the messiness of gender politics. By drawing attention to the gendered experiences women encounter while pursuing and maintaining educational leadership positions, this study helps pave the way forward for administrators, policy makers, and those interested in the aims of gender justice.