I failed my students as a first-time principal. By not speaking up for students on the margins, I was complicit in maintaining a status quo that was morally and educationally reprehensible. As a second-time principal, I attempted to rectify challenges from my first principalship and to lead in a culturally responsive and socially just way. This autoethnography explored how culturally responsive and socially just leadership is manifested in practice. Using vignettes, I presented data detailing my process as I learned to practice culturally responsive social justice leadership. Next, I analyzed and categorized the vignettes to find meaning based on adjectival categories that emerged as the data were thematized. My analysis utilized Noddings’ Caring Theory to arrive at deeper meaning. Based on the extant literature, adjectival categorization, and Caring Theory conceptual analysis, this autoethnography sought to provide insight into one principal’s attempts to lead in a culturally responsive and socially just manner. My findings were: historical and present context matter in leading a school, Culturally Responsive Social Justice Leadership (CRSJL) moved from individual conversations to whole-school action, and the efforts to be a CRSJL exacted an emotional toll, required persistence, and proved that the change process was difficult.