Situated in West's (1993) politics of difference theory, this article is based on the author's experiences teaching a multicultural foundations course as a Black faculty member for sixteen years at a predominantly White institution (PWI). Employing autobiographical self-study as a methodology, challenges and strategies for teaching while Black are outlined in a three-level typology--which includes the naiveté, transformational teaching, and belvedere levels--assists marginalized instructors in reflecting on and reconciling oppressive PWI classroom environments to thrive in one's career. The complex nature of teaching within marginalization at PWIs is addressed throughout.