This article explores three recent books related to World Englishes studies and considers ways they overtly and implicitly frame the politics of the field. The author also describes some of his own experiences working with graduate students that suggest a disruption of traditional dichotomies between single standard and pluralistic models of English spread. The author shares some pedagogical materials designed to provoke deeper discussions of the personal and political dimensions of language variety and identification. Finally, he concludes with a call to consider how Canagarajah's notion of "translingualism" may lead to updated political frameworks that embrace the transformative potential of languages, speakers, and societies.