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This study challenges conventional interpretations that frame Platonic paideia as a singular pursuit of order by re-examining The Republic through a dialectical lens. It argues that order and disorder are not opposites but exist in dynamic, mutually sustaining tension and symbiosis. Through hermeneutic analysis, this dialectic is traced across cosmological, political, psychological, and epistemological dimensions, where ordered Ideas remain inseparable from disordered experience. This classical framework is then used to illuminate contemporary educational crises that swing between hollow standardization and normless openness, both of which suppress authentic individuality. The study ultimately offers practical wisdom for educators—one that embraces the creative tension of order and disorder as the foundation for a resilient and reflective educational practice.