The chapter proposes a reflection on the experience of an academic planner appointed to the executive body of the Apulia regional council, southern Italy, for 10 years. After highlighting some dilemmas embedded in such a difficult double role in a context characterized by an old land use planning system and huge expectation of change, the article focuses on the case study of the so-called “area of Paduli”. The different processes taking place in this area involved the author in a blend of enabling and contrasting actions. They disclose how the author interpreted her role in politics, as involving continuous direct interactions with local municipalities and more or less organized citizens and groups, connecting top-down vision and bottom-up initiatives. This fed a new collective interpretation of ‘territory’, as an intermingling of material and immaterial heritage to be protected and enhanced through social appropriation processes for more just and durable regional development.