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During a time when legislation seeks to de-emphasize and de-legitimize identities and intersectionalities, it is more important than ever that we offer collective support and community to those who continue to hit glass ceilings and land on glass cliffs. This study uses a feminist lens combined with the constructive-developmental theory to examine the stories of 12 female school district leaders across the state of North Carolina who aspire to be superintendents. With data gleaned from semi-structured interviews, this study reveals the internal and external barriers they face, strategies to overcome these barriers, and advice for other women who desire to be school superintendents.