The future of cities and their spaces lies in the redevelopment of existing housing stock and its associated transformation tasks. The discipline of urban planning needs to reposition itself, and—at the intersection of climate change and the mobility revolution—seek to champion the cause of increased participation and greater resilience. How can challenges be overcome in the face of more stringent planning requirements, faster implementation times, and limited resources? Renowned experts from the fields of urban policy, city management, and both practical and academic urban planning discussed the future of cities and urban planning at three symposia hosted by the Professor Albert Speer Foundation. Their arguments encourage us to leave behind established patterns of thinking and approach the tasks of the future with visionary ideas.