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John Steinbeck's formal schooling experiences shaped his worldview of education as a series of dreary classrooms in which children studied "subjects in which no one was interested." Yet he had great reverence for teachers and envisioned teaching to be an art form with potential to awaken the mind and spirit with curiosity, while also providing literacy opportunities for the children of migrants and the poor. From this perspective, his vision aligns with that of John Dewey, Jane Addams, and other progressive reformers. Steinbeck's hatred of formal schooling, combined with his progressive beliefs about the power of learning, reading, and inquiry, shaped both his fictional portrayals of schooling and also his persuasive essays on related subjects. This analysis of Steinbeck's attitudes toward education has a triple focus: his own experiences as a student; the state of the contemporary educational curriculum, policies, and practices; and the experiences of his fictional characters as they encounter formal and informal educational opportunities. The study reveals connections between Steinbeck's work and a surprising range of educational issues—from compulsory attendance to the contrast between rural and urban attitudes to classism in higher education. Although Steinbeck did not propose an educational or curriculum design, in his own life he modeled the value of participation in the act of learning—chiefly by seeking out excellent mentors and reading broadly. Thus, the examples set by his own life and in his fiction continue to challenge an educational system focused on conformity, often to the neglect or exclusion of creativity.