This article discusses ways in which we can connect empirical data and design skills to create more circular and sustainable urban areas. The case of Hellersdorf-Süd (Berlin, DE) is used to describe a design approach that is context-driven and combines data and design skills to formulate coherent and relevant design proposals. Based on this exposition, this article presents and exploration of the future urbanist practices in which sustainability and circularity on a conceptualized larger scale. As such, it provides a speculative account of a future course of action to achieve urban sustainability and systemic circularity.