Changes in agriculture, including simultaneous intensification and abandonment, have significantly shaped the evolution of rural areas. The assessment of resilience in agricultural systems could provide insights into the ability of many rural areas to survive and regain competitiveness following disturbances. The aim of this study is to use the adaptive cycle heuristic as a diagnostic tool to study dynamics of change in two agricultural sectors (durum wheat/sheep and goat farming) in the Basilicata region of Southern Italy over the last seventy years. The heuristic was applied through a participatory approach in a community of stakeholders who have conceived, in collaboration with researchers, the Manifesto “Let’s Think Basilicata” as a regional instrument of analysis and a laboratory of ideas and development of proposals. Despite some methodological difficulties, the adaptive cycle heuristic proved useful to describe processes of change in the socio-ecological system and could have enormous potential in shaping policy instruments for rural areas. However, much greater research is needed, both in terms of theory and methodology, before policy impacts on resilience in socio-ecological systems can be fully understood.