In one year, I moved from a diverse school where I felt pretty and smart to a predominantly White school where I felt ugly and dumb. This autoethnography examines how a little African American girl’s transfer from an urban to a suburban school resulted in a paradigm shift that had and continues to have profound consequences on her identity development and subsequent choices and practices as a marginalized student struggling to succeed academically, a teacher grappling with professional identity, and a doctoral student hoping to help preservice teachers prepare to meet the needs of diverse students. The research question that prompted this exploration is How does teacher-student (dis)connection impact the identity development of students of color in U.S. schools, and these same students’ professional identity development should they later become teachers themselves? In a larger social context, this work examines the impact of a culture of care, or lack thereof, in the milieu of teaching and learning, especially as it relates to the academic and personal growth and development of Black and Brown students in U.S. public schools. The inquiry aids in unpacking, storying, and restorying the school-related lived experiences of the researcher. The narrative exemplars that are illuminated reinforce the personal, relational, and professional significance of creating a school and classroom culture of care; and the “truths” revealed may offer new knowledge that encourages today’s teachers to develop behaviors and practices that lead to safe, productive, culturally solicitous learning environments.