With this design studio we explore possible ways of reframing our work in the spatial design field with considering current environmental concerns, changes in the places we live in, and our attitudes towards time, memories and legacies of the past. Discussing “design in context” with the construction of a library of references which were critically analysed, and approaching how these issues unfold in relatively ordinary settlements in Alta Brianza, we had the opportunity to reconsider common approaches to regeneration that may sometimes miss the point of cycles of life that are simply interrupted. Students’ proposals imagine new urban cores revolving around agricultural production and waste treatment, different approaches to care and ageing population, ideas of wellbeing that question private and public spheres.