The cultural experiences of minority learners are often omitted from the formal curriculum leading to exclusion and a sense of cultural loss. In this study, the researcher's lived experience serves as the basis to develop a novel research strategy: transformative autoethnography. The researcher uses the method of autoethnography to more deeply understand his roles as Chickasaw and adult educator, amplified by his unique role as the developer of a tribal learning community situated at a research university. This immersive experience serves as the context for self-reflection, which includes an educational history marred by my perceptions of Whiteness and lack of cultural connectedness. Transformative learning theory serves as the theoretical framework by which the author comes to appreciate the intersection of culture, identity, and meaning. The research context is triangulated with the experiences of other Chickasaws, including learning community participants, providing an autoethnography steeped in phenomenological thought. This credible qualitative account serves as a roadmap for the educational journeys of Native Americans and other minority adult learners and the educators, advisors, and program developers who strive to support them.