In this article I problematize the reasons for and methods through which I incorporated an opportunity for experiential learning, via a Community Inquiry Project, into my own teaching. I take the stance of a teacher-researcher to closely analyze the specific documents and tasks used to introduce pre-service teachers to the project. I draw on sociocultural approaches to teacher development and literature on experiential education in teacher education to provide a background for the project and the self-study and offer critical whiteness studies as an appropriate lens through which to analyze the various elements of the project. Findings from this study suggest that the project limited the pre-service teachers' characterizations of community, understandings of sociocultural approaches to learning, relationships to the community, and perceptions of the role of community in teaching. I draw on these findings to suggest that teacher educators share their reflective practices with their students and learn about the diverse experiences of the pre-service teachers themselves to better prepare them to inquire into and draw on knowledge of communities as they work with diverse populations of students.