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This paper reports on a self-study in which I examine my professional journey and positionality while teaching in mid-west Wisconsin, under President Trump’s political influence, and teaching a Foundations of Multicultural Education course to students from rural backgrounds, lower-middle class, and white females. As a passionate advocate for social justice-based teaching and research, a Canadian citizen, and a racialized woman, I faced many conflicting experiences within myself about teaching. The study examines how my positionality was responded to, how my choice of curriculum for my course was received, my beliefs around social justice, and communal responsibility towards my students. With the use of these personal and professional sources I provide insight on the challenges, opportunities and possibilities I encountered.