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This paper is an exploration of the lessons learned as a Graduate Teaching Assistant in the Philadelphia Urban Seminar and their influence on my praxis as a teacher educator. Participating in this liberatory educational project challenged pedagogical projects rooted in white supremacy and domination. It provided the space for both collective and individual reflection on other possible ways of educational praxis. I reflect on how this experience and Extraordinary Pedagogies (Staples-Dixon, 2024) were instrumental in facilitating Teacher Negotiations, sustained and informed conversations about fear, power, and choice for preservice teachers seeking to enact anti-oppressive pedagogies in Texas classrooms during a standalone diversity course across the years 2021 to 2024. I argue that disclosing fears and anxiety about anti-oppressive teaching, examining political discourses, and engaging in deep reflexive practices are the Extraordinary Pedagogies needed for teacher education in the 2020s.