The strategy of a State and the economic performance of a region mutually reinforce each other. In fact, on the one hand, State policies and organizational and legal frameworks influence the performance of enterprises in a territory and their localization strategies. On the other hand, such enterprises behaviour influences State tax income and the value generated in a territory. Ignoring such feedback loop in State strategic planning by implementation of aggressive austerity measures may perhaps generate some financial benefits in the short term, but may generate vicious cycles discouraging enterprises development and leading to lower tax collection and value generation in the long run. This innovative study aims to frame, through a system dynamics approach, the complex feedback relationships between enterprises behaviour and the Italian State's financial performance. A critical analysis of main Italian State planning cycle’s weaknesses is outlined and a new framework analysis based on a "holistic development" approach is proposed.