Cities are the victims of their own success. A modern first-world city is a marvel, with incredibly intertwined systems doing all sorts of things. They provide housing, transportation, employment, education, food, health care, and entertainment to their millions of citizens. Cities are the most economically productive kind of communityCommunity, which is the primary reason that the world is rapidly urbanizing. But the average citizen of a modern city still faces persistent quality-of-life problems—affordability of housing, inefficient transportation, an unsustainable environment. We think we could do much better in urban designUrban design by adopting an approach borrowed from software development—User-Centered DesignUser centered design (UCD). The “user” in this case is the ordinary city dweller. “Centering” means to focus design decisions on the citizens’ tasks, rather than the competition between and within government and industry silos. In this paper, we argue that the UCD approach requires a holistic, cooperative mindset. We present technological advances that can enable this more cooperative future. We illustrate our approach with concrete proposals for two of the most important aspects of urban living—housing and transportation.