This research article by Lisa Collins at the Graduate School of Education and Counseling at Lewis and Clark College addresses organizational learning and racial healing in schools. The researcher used auto-ethnography to investigate her experience as a Black school leader in Oregon’s system of public education. Using the framework of Black feminist thought, the author explored topics such as settler colonialism, civil rights, and school bureaucracy and then proposed a pathway toward racial healing based on the STAR: Strategies for Trauma Awareness and Resilience. The article proposes that communities of support are needed and that preparation programs must provide educators with an understanding of how schools function as oppressive systems for the adults who work within them.