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Part of a larger study examining the experiences of 15 Black and Indigenous women educational leaders in Ontario, this paper details the findings on the Black participants. This paper will explore Black women’s challenges and motivations in leadership. The research team conducted virtual semi-structured interviews, all recorded and transcribed. Data analysis was framed by Black feminist theory and critical race theory in education, specifically counterstorytelling and intersectionality, which fostered understanding of Black women educational leaders’ experiences, methods of caring and nurturing, and systems of accountability. Findings reveal the ways Black women ground themselves in their Black identity and draw on legacies of resistance to combat the challenges encountered in their leadership, and also frame their need for healing.