The ideas presented in this book are a conceptual leverage to correct the rigidity of top-down practices and bring the real city, or the city of everyday life, closer to the city of conventional planning. Considering self-organization as the starting point at the base of complex systems, this book tries to understand how specific qualities emerge and evolve from this behavior. For this, the book discusses new ways of looking at and understanding cities by applying holistic methods and approaches based on the conceptual grounds of quantum, fractal, and complexity theories. The book highlights the fact that the information on how to transform and build a city is contained within the city itself. In this regard, some methodological steps to unpack complexities and translate the essential qualities of space into potential generators for city design and planning are provided. The book urges courageous experimentation and proposes a methodology where the computational nature of urban phenomena goes along with historic anthropological ideas, thus emphasizing the characteristics of a specific reality in a model. They do not exclude each other; in fact, they are part of the unbroken web of wholeness. Importantly, the proposed methodology supports gradual and natural coevolution process in the city through combining planned and unplanned actions and the involving multiplicity of actors, impacting on Urban Planning and Design Practice.