In this response to Molly Ware's review of our 2013 book, "John Dewey and Education Outdoors," we extend her suggestion that complexity be regarded as an important, generative force in education reform. Drawing on Dewey's 1933 "Utopian Schools" speech, we discuss the "level deeper" that Dewey sought as he criticized the method/subject mater dichotomy, which he saw as an artifact of social class carried forward in the form of a curricular debate rather than a natural source of tension that would be productive to democratic education. Dewey radically argued that "learning" itself contained similar anti-democratic potential. Eschewing the false child versus curriculum dichotomy, Dewey believed complexity as a catalyst for educational action would be achieved by engaging children in historically formed "occupations," harnessing the forces that drive technological and cultural evolution in order to spur interest, effort, and the formation of social attitudes among students. Following Ware, we suggest that reformers should seek to understand at a lever deeper the many sources of complexity they encounter as they both challenge and honor what is.