In our efforts for more sustainable systems, we often adjust the current situation instead of finding new solutions. These preservation scenarios have little room for the type of radical societal change that today’s increasing social and environmental challenges demand, but there are always alternatives. This chapter plays with different ways of thinking, understanding, organizing, collaborating, and prioritizing in cities that could potentially take us towards more sustainable and inclusive societies. We need more flexible systems that allow place-based solutions to develop more organically, and municipalities should have departments responsible for interdisciplinary local community work. Physical meeting places are important to allow more social and spontaneous city life, and it is important to ensure that local communities get to participate in urban development to safeguard liveability. Public health, and environmental and social sustainability often go hand-in-hand.