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This dissertation explores John Dewey’s vision of democracy as a mode of associated living, examining its enactment in contemporary K–12 classrooms. Set in _____ during a shift toward open, competency-based education, the study investigates how this evolving framework enables Deweyan principles in practice. Through a year-long collaborative inquiry with 14 educators, it examines how teachers navigate tensions between democratic aspirations and entrenched schooling norms. Framed by the metaphor of democracy as rich and rough terrain, findings highlight four themes: conversation and study, reckoning with control, nurturing ecosystem kinships, and practicing freedom. Amid global uncertainty and calls for a return to basics, this research underscores the value of critically reflecting on efforts to realize Dewey’s democratic ideals in education.