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This paper presents a portrait of one teacher activist connected to a grassroots teacher organization in New York City. Designed to explore how teacher activists understand and do their work, the study uses the methodology of portraiture to understand and explain the development of teaching and activism; how teacher activists attempt to put their activist commitments into practice; what challenges, barriers, conflicts, and contradictions they face in their work; and, what sustains and supports them in their work. To understand teacher activists is to understand their social and political lives and contexts. These understandings move us beyond the school walls in order to analyze the lives of teachers as crucial to the development of their practice, dispositions, ideologies, and perspectives.