Harsh critiques of the utopian visions of modernist architects have led many of today’s designers to seek to fit their constructed responses into the mainstream culture (Schneekloth, 1998). While undoubtedly the works of most designers are grounded in the intention of making the world a better and more beautiful place, the underlying desire to fit in with the mainstream leads implicitly to confirming the status quo of the built environment. We believe that if designers are to move toward envisioning and creating more sustainable urban futures they must eschew the desire to fit in and carefully and methodically reconsider what is possible. To that end, in this paper we explore the motivations, methods and outcomes of five students in their penultimate design studio of the Masters of Architecture program at the University of Illinois at Urbana-Champaign. Using three measures, motivations, methods, and outcomes, as evidence we seek to understand how future designers, as they complete their education and embark on careers in the design professions, comprehend and envision an urbanization process that results in a sustainable urban future.