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This qualitative thematic analysis examines the experiences of 23 educational leaders who hold at least one LGBTQ+ identity. This study examines how LGBTQ+ educational leaders have navigated their careers and the role of support systems and structures. We situate the study within the work of historians of education who have detailed out the experiences of LGBTQ+ educators over the 20th century. We lift three major preliminary themes: cisheteronormative schools; allyship and supportive supervisor; and mentorship, community, and possibility. This study contributes to the limited literature of LGBTQ+ educational leaders and points toward important considerations for leadership development to create more welcoming spaces for LGBTQ+ individuals.