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This collaborative self-study explores tensions that emerged in facilitating dilemma-of-practice dialogues with secondary student teachers in a white-dominant teacher education program. As emerging and practiced teacher educators, we were challenged when student teachers’ language defied critical dispositions that were embedded in program culture. We recognized such harmful repetitions as oppressive, but we were challenged in different ways by how to interrupt them. We also experienced compassion and interruption as competing aims. Drawing on critical perspectives on whiteness, anti-oppressive education, and compassionate pedagogy, we theorize the tension that emerged in the space where compassion and aims of justice-oriented teacher education intersect. Paired with practitioner inquiry, these perspectives supported us to critically examine our own learning and practice.