The challenges cities and regions face now and in the future are enormous and uncertain, to be determined or affected by unexpected extreme events like pandemics, economic crises, and climate change. So, it is urgently needed to get beyond the dichotomies in urbanism, and, by default, urbanism should have the nature to combine these perspectives. To move forward, people involved in urbanism should be aware of each other’s knowledge, qualifications, and worldviews, taking any opportunity to transcend and connect different discourses to invent better ways of achieving resilience and sustainability. With the ambition to create such opportunities, the 14th conference of the International Forum on Urbanism (IFoU) in 2021 called for papers to contribute to dialogues in five tracks that represent five types of debates over a set of dichotomies. 1. “Urban-rural Integration” and “Areas In-Between” 2. The City is an Object and a City is in Transition 3. Political Ecology and Adaptive and Transformative Framework 4. Metropolization and the Right to the City 5. Human-centred and Nature-based Approaches in Cities