The purpose of this theoretical exposition is to bring two fields into discussion concerning the issue of motivation, in the new monetized context of education, through an encounter between John Dewey and self-determination theory. Using Dewey's Experience and Education as well as self-determination theory's most fundamental scholarship (e.g., Ryan and Deci 2000), we offer a contemporary parallel with Dewey's thoughts on "New" and "Old" education and examine it through the lens of self-determination theory. This interdisciplinary perspective combines educational psychology with philosophy of education to retheorize motivation as a critical response to the "New" educational shift toward monetization, which we argue should be resisted.