This chapter discusses the need to redefine how we read and understand cities in order to formulate the specific questions and goals that inform the design of the sustainable city. Looking to history as a continuum and to the city as an evolutionary process, Stockholm and Umeå were studied from the perspective of their connection to a common web of towns, which led to trace influences and processes that have shaped them and to identify four historical moments that explain key urban transformations. Particularly the 17th century, when both were rebuilt and re-signified as administrative nodes of the web of towns that the centralized and bureaucratic Swedish state imposed on top of a pre-existing network of trading settlements. It is argued that these two urban systems require different narratives about the dynamics that shape them, how they function, and how citizens relate to them; that there is a continuity in the way cities were approached between 17th and 20th centuries through a sequence of urban models rooted in ideas of improvement, capitalism, rationalism, and mechanism; and the importance of the internal generative processes of cities, enhanced by the exercise of citizenship, civic action, and proximity to civil institutions.