As a committed social justice educator, I share in this dissertation a theoretically informed instructional autoethnography of my time teaching and researching as a Language Arts and Speech teacher across two different public high schools and two different school years. My story of learning to embody the values and practices of progressive teaching arises from the central research questions: "How can I, a self-identified progressive Language Arts educator committed to social justice, learn to implement critical, democratic, responsive, and holistic pedagogy as a public high school teacher in this particular region at this time in U.S. public education? And, within these particular schooling cultures, what aspects of these schooling environments support or inhibit my ability to perform as a progressive educator?" Responding to critiques of public schooling policy and practices, my work is grounded in theoretical commitments of progressive education articulated by the critical pedagogy of Paulo Freire and those North American educators who have brought his libratory praxis forward into what I call connected, social justice pedagogy.