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Transition planning should focus on comprehensive supports that meet students’ individual goals including in-school and community experiences. Research has revealed however, that students continue to lack transition preparation and experiences. In this qualitative study, we interviewed seven teachers of high school students with disabilities. Applying integrated frameworks of person-centered planning (PCP)and Yosso’s (2005) Community Cultural Wealth, we engaged in abductive analysis, which generated three themes. All themes were permeated by an overarching concept of a deficit-to-asset continuum, impacting how teachers perceive of and provide access to opportunities for transition. This study includes a teacher-exemplar of transition praxis, who described her methods of resistance, extending transition beyond the school walls. Implications include ways to reimagine possibilities and opportunities for students’ futures.