As a result of the increasing demands and the changing multi-cultural and socio-economic profile of schools, shortages of quality education leaders are a global issue. In the United States, this is particularly pernicious in urban areas, and traditional pathways to leadership positions pose an array of barriers. There is a growing need for culturally-responsive, critically self-aware social justice-oriented (CR/CSA/SJ) leaders who are better able to retain diverse teachers, more likely to stay in urban schools, contribute to higher achievement of marginalized students, and create inclusive environments. This qualitative study uses interviews to examine the leadership pathways of 72 education leaders at 28 intentionally diverse charter schools across five U.S. locations. Findings suggest that a range of motivations and experiences facilitated their pathways into leadership positions. Implications are relevant globally, at this time of increased awareness of historic societal inequities that schools can help combat.