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All gender identity is socialized, but anything gendered feminine is marginalized. In the United States, we live in a patriarchal culture that is bounded by binary gender identity. Up to this point, work on gender and education leadership has remained within the bounds of patriarchy, and thus been confined to binary, hierarchical gender definitions. This study pushes past prior work to advance a more complex and messy understanding of how identity impacts aspiring leaders in their careers. Using Carol Gilligan and Snider (2018) Listening Guide Method, this study of 18 aspiring school leaders of different gender identities, sexual identities, and races focuses on how gender identity and gender performance impact school leaders' career trajectories. A key finding of this study is that women, regardless of race or sexual identity, have difficulty finding mentors while men, regardless of race or sexual identity, are tapped by schools leaders and offered mentoring opportunities. This chapter posits a new framework for mentoring that will lead to more liberatory pipeline structures.