Enough time has passed to reveal that the systems that gives form to modern citizenship no longer serves the interests of the majority of urban populations. Aspirations of inclusion in the functioning and performing life of the city are no longer guaranteed, and the promise of modern urban citizenry is no longer open to all. This reality directly undermines the elixir of modern society and reveals the cleft between the diverging interests of how the city is built and how the city is lived. In the words of Rousseau on the Social Contract "The real meaning of this word [City] has been almost wholly lost in modern times; most people mistake a town for a city, and a townsman for a citizen. They do not know that houses make a town, but citizens a city". Institutions set up to ensure the civil interests of the population have yielded to emerging and sanctified practices of economic extraction aimed at the housing market. The success of such practices have left indelible marks on the basic lived experience of urban life in which mass foreclosure, spatial downsizing, and retreat to the periphery pressure all aspects of citizen habitation. Architects and planners have been powerless to respond either theoretically or practically. Despite this, citizens are turning to self-made spatial adaptations, covert systems, artful disobedience, and experimental living models as a form of inventive resistance to the new context. Such revelations offer new clues as to how emerging urban design and architecture practice can be reinvented as a value based proposition to serve broader societal interests.