Eco-imagination for a sustainable future must be rooted in urban regeneration and involves strong attention to the physical and social context. We are witnessing a paradigm shift, which now aspires to attribute direct responsibility to local communities in the transformation processes, especially interacting with the cultural heritage they feel their own. While, on the one hand, the “Council of Europe Framework Convention on the Social Value of Cultural Heritage” launched in Portugal in 2005 anticipates and consolidates an effective methodology for involving local actors in the participatory process of valorizing the “common goods”; on the other hand, the many disciplines that are called to govern this process try to develop innovative tools and methods, capable of communicating with each other and “turning the telescope upside down”, so to say, I mean giving multiple subjects and citizens a foundational role in process of transformation of common goods. Before introducing the Faro Convention, I propose some reflections on the complexity of the management of Venice’s outstanding value, as well as on the role of a discipline such as architecture, a leading player in urban transformations, especially in the case of Eco-imagination. I am basing them on the research of one of the most complex and multifaceted figures in the architectural panorama of the second part of the last century in Italy and abroad: Giancarlo De Carlo, my teacher and mentor.