This essay aims to demonstrate the theoretical purchase offered by linking Dewey's educational theory with a rigorous account of dialectical development. Drawing on recent literature which emphasizes the continuing influence of Hegel on Dewey's thought throughout the latter's career, this essay reconstructs Dewey's argument regarding the detrimental effects of "external aims" (e.g., grades, standardized test scores) in education with a specifically Hegelian framework. The goal is to show how emphasizing and drawing out the dialectical character of Dewey's conception of individual experience clarifies his case for why external aims hinder the continuous individual growth that democratic education aims to cultivate. (Contains 8 notes.)