In this collaborative self-study, teacher educators/researchers in four different geographic, social, and cultural institutions of higher education implemented Culturally Proactive Pedagogy (CPP) learning events into their undergraduate literacy methods courses. Conceptually, this study used the Pose, Wobble, Flow (P/W/F) framework developed by Garcia and O'Donnell-Allen to build upon theories of culturally responsive teaching and culturally sustaining pedagogies. Our primary research questions were: What are our poses, wobbles, and flows while implementing culturally proactive pedagogies in literacy methods courses? What is learned from engaging in a self-study with critical friends? We acted as participants, teachers, and researchers throughout the self-study. By taking on these multiple identities, we hoped to grow and reflect on our personal and professional journeys as educators. Through a series of shared learning events taught in each of our classrooms, we collected data based on our reflections, monthly video meetings, and assignments completed by us and with our preservice teachers. Individual findings present each researcher's poses, wobbles, and flows in implementing CPP. Additionally, the ways privilege, collaboration, and accountability through critical friends emerged as lasting lessons in this self-study research.