This chapter examines the teaching and learning experiences of the instructor and students engaged in a cultural proficiency doctoral-level course. The author uses autoethnography to provide the readers with insight into the author's fears, frustrations, and overall approach to creating an environment conducive to fearless conversations. Careful attention is also given to student perceptions of the course content. The author offers practical suggestions for fearless teaching and encourages professors to be authentic, vulnerable, and bold as they work to develop inclusive classrooms where all voices are valued.