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This study examines the factors which influence 11 Black female teachers’ career trajectories and aspirations as they weigh the decision to move from teacher to administrator. Black female teachers frequently also encounter both racism (Frank et al., 2021) and sexism in the workplace (Farinde-Wu et al., 2020; Reed, 2012). The purpose of this study is to characterize the experiences of Black female mathematics teachers as they decide whether to pursue administrative positions. We examine the factors involved and systemic issues that factor in their career opportunities and decisions. Black administrators, not only diversify leadership, but may also lead to improvements in organizational functioning, teacher retention, and student learning.