The purpose of this article is to reflect on how racial and cultural stereotypes so deeply embedded in our daily experiences frame and impact our thoughts, emotions, and behaviours. There are moments interpersonally and in groups when embedded assumptions and stereotypes seem to clash at the boundaries of social identities and roles, a space that can be shaming because we think we should know better. In this article I share journal entries of a group of women who I invited to work with me on a research team. I offer journals of our experiences of difficult moments at the boundaries of race, ethnicity, and social class as opportunities for learning. The journals provided an opportunity to share often unspoken thoughts and feelings about our racial and cultural points of disconnection.