This book examines the trajectories of a transnational group of teachers of African descent who made the decision to live and teach English in Japan. Through a layered analytical framework this book examines how these teachers negotiate their professional identity and legitimacy in contexts that may be professionally supportive in some cases, but professionally challenging in others due to issues around language, culture and race. The author argues that while multiculturalism and diversity within ELT in Japan may seem to be gradually improving, raciolinguistic native-speakerism still affects the livelihood of racialized teachers. The book also suggests that the agency they can exercise in teaching about Black culture and Black Englishes appears to be limited by the constraints of the local institutions in which they teach.