Trans-speakerism allows for an emancipatory approach to be taken in understanding the relationship between language speakers and their identities, a concept arising in an effort to move away from the “native” and “non-native” speaker dichotomy. However, one unrealized and ironic potential effect of this framework is helping native speakers realize the privilege they hold—particularly, native English speakers. Using an autoethnographic design, I will account for and analyze my embedded experience as a foreigner living and working in Japan as a native English-speaking language teacher who is Black. The analysis is grounded in the intersection of race, identity, privilege, and the critical tension points of each. In addition to the personal narrative of the author (while being cross-referenced by relevant literature, artifacts, and others in the field), I called upon four colleagues in my community of practice to add their insights regarding race, identity, and privilege as professional teachers of the English language in Japan. An open-ended questionnaire was used to gain their thoughts. The collected information resulted in a deeper understanding that while race is a reality we cannot escape, the fact that we are native speakers of English affords us a certain privilege within our chosen profession. A privilege others may not have. Recognition is vital if we truly want to progress as professionals and community.