As two white female teachers, we look back on our teaching experiences in Hong Kong and Northern Alberta to disrupt problematic diversity narratives from our first classrooms. Through critical auto-ethnographic approaches and cellphilming (cellphone + video-production), we analyze our engagement with privilege within our classrooms. We found that we both promoted uncomplicated conceptions of diversity, and each engaged in what Eve Tuck (2009) has described as damaged-centered approaches--teaching practices that established, "harm or injury in order to achieve reparation" (p. 413). We see these experiences as a case study in how to look back productively to change the way we teach in the present and future toward visions of justice.