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This paper presents findings from a two-year study into the role(s) of comfort and discomfort in graduate students’ experiences and their analyses of issues related to culture, race, and equity. In adopting a framework of comfort/discomfort for understanding participants’ differing positionalities, the study questions pedagogical assumptions and intentions about what it means to engage in transformative learning in educational spaces, examining the issues within three areas: (1) conceptualizations and questions related to difference, social justice, and equality; (2) generation and application of knowledge within and outside classroom contexts; and (3) integration of these issues into students’ stated sense of identity and their emerging theories and understandings of learning as emotional labor, comfort, and discomfort.