With disproportionately high attrition rates for teachers of Color, there are many lessons to be learned from veteran teacher leaders that can inform how we train teachers. In this article, I share analysis of interviews with 11 women of Color veteran teachers who serve in formal or informal leadership roles within social justice education. Their reflections reveal how teacher education programs—justice oriented or not—fell short in preparing them for the hostile racial climate of schools, thus putting them at increased risk of being pushed out of teaching. This article also points to collectivized teacher-led spaces of racial literacy development—framed as critical professional development (CPD)—that have helped to sustain them in the field. These teachers’ narratives offer significant insights for teacher education to better prepare teachers of Color for long, effective, and transformative careers.