This article reports on a two-year self-study exploring my roles and evolving philosophy as an early childhood teacher educator teaching diversity in the US. I was interested in better understanding how and what I can learn from the complexity of my teaching experiences. Data included my professional journals, students’ reflection journals, and communication with a critical friend. I examined, when teaching diversity, how I constructed and navigated my roles, how the students constructed and perceived my roles, and how they have transformed my instructional philosophy and practices. The findings illustrated a dynamic and tension-filled experience of a teacher educator teaching diversity in the US as a perceived outsider, suggesting that it was a reflexive learning opportunity. The findings are aligned with a growing recognition that appropriate time and space is necessary for teacher educators to share and exchange their experiences and to gain support for their professional development when teaching diversity. Further, the findings are supportive of the contribution of self-study research in advancing the broader field of teacher education research.