"Disenchantment" has been a popular trope in the social sciences since Max Weber's appropriation of the term nearly a century ago. In recent years, however, scholars have come to argue that, in contrast to the standard modernization story of unabated rationalization, organizations have long been subject to countervailing forces. In this essay, David Diehl uses modern reinterpretations of the "disenchantment" thesis to suggest that the structure of contemporary schooling is the product of ongoing cultural efforts to re-enchant public life by infusing rational bureaucracy with Romantic impulses in order to combat alienation and social fragmentation. Moreover, Diehl argues that the changing relationship between rationality and Romanticism has taken a unique form in the contemporary period and that recognizing this helps us to better understand the paradoxical modern push for schools to achieve seemingly incompatible goals such as diversity and standardization, community and accountability, and creativity and efficiency.