This phenomenological study employed purposive sampling to interview 30 successful women on the supports, barriers, and strategies to succeed as leaders. Participants were Black, Asian, Native American, Latinx, White, and mixed race, ages 30 to 80 years of age, cis- and transgender, and in the LGBTQ community. Deductive coding identified themes and related concepts with findings confirmed by participants. Findings reveal numerous persistent issues: gender-based behavior and appearance expectations, internal organizational threats, the impact of family, women who support/hinder success, mentors, perceived competence, and effective responses to sexualization and gender stereotyping. The findings of this study have implications for principal preparation programs, human resource departments, school boards, school leaders, and mentors of women leaders.