Within the framework of research projects for the Italian National Recovery and Resilience Plan—Mission 4 Component 2 “From Research to Enterprise”—the contribution aims to propose a reflection on one of the possible research methodologies in the field of architectural and urban design, with the case study of the doctoral project “The Challenge of Sustainable Mobility,” co-funded by Milano Serravalle Tangenziali, concessionaire of the Milan ring roads. The approach refers to research-by-design—method based on formulating design scenarios that can instruct and enable critical-theoretical discourses, with future implemented translations. The adopted method is also known in the literature as meta-design, based on Van Onck's definition. Metadesign requires a certain sense of disorder that responds to that degree of uncertainty typical of strategic planning in defining solutions as an abacus of design in power rather than in action. The prefix meta-itself restores the transformative, changing, and incremental character that embodies strategic design open to more punctual forthcoming declinations. It is a preliminary methodological effort that aspires to define principles and guidelines as the outcome of a process effort rather than a formalization of concluded outcomes typical of traditional planning. The contribution aims to present reflections on the Metadesign alternative methodological process, applied to the potential of an atlas of residual spaces close to Milan’s ring roads. The ambition is to return an intermediate tool to guide operative actions in the medium-long term in the spatial context of Ring Roads, aspiring to build an exportable method on comparable scenarios starting from site-specific cases.