The purpose of this research was to explore how the personal and professional experiences of school leaders strengthened or hindered their ability to engage in social justice leadership to advance educational equity and encourage culturally proficient practices in their schools. I employed a descriptive multi-case study and the research was viewed through a conceptual framework that included social justice, equity, and the five elements of cultural proficiency. Five principals from three different school districts were selected as participants. They represented elementary, middle and high schools. Interviews consisted of semi-structured face to face interviews with each principal participant and one focus group interview with five participants. Each participant also provided a cultural autobiography. Findings revealed while principals may care deeply about providing equitable opportunities for students, the interest does not supplement knowledge, skills, experience, and support. The information gained from this study can inform the practice of school leaders, and the way in which districts and programs of educational leadership prepare school leaders to serve and address the needs of all students as public schools become more culturally diverse.