This paper reports on the narrative of Shannon, a Taiwanese Canadian female assistant language teacher (ALT) of the Japan Exchange and Teaching (JET) Programme, one of the world's largest government-sponsored programmes for recruiting English language teachers to teach overseas [Nagatomo (2016). "Identity, gender and teaching English in Japan." Multilingual Matters]. The interview data were analyzed with the methodology of critical discursive psychology (CDP), a version of discourse analysis developed by Wetherall and Potter (1992. "Mapping the language of racism: Discourse and the legitimation of exploitation." Harvester Wheatsheaf). CDP allows the researchers to engage in 'double movement' of Marxist ideological critique and Foucauldian genealogical analysis, with which I demonstrate how Shannon's subject position was conditioned by broader ideologies and discourses about race, gender, and language. My analysis highlights how the ideology of native speakerism impacts an Asian native speaker's experience as an ALT in Japan with a particular focus on Shannon's struggle in a dilemmatic subject position between Asian Self and foreign Other. Due to her Asian appearance, Shannon constantly felt that she was 'not foreign enough' to fulfil the role of an exoticised native speaker and struggled to negotiate her legitimacy as an English teacher. Taking dilemma as a generative space for change, I discuss potential pathways for ideological critique and discursive transformation.