The chapter offers a unique perspective on strategy development and the role of a strategist, highlighting the importance of context-specific thinking, flexibility, and reflection. The chapter begins by examining Dayan’s early experiences as a revolutionary guerrilla fighter, which shaped his view of war as a phenomenon that can only be understood in its local, concrete geographical, cultural, and political contexts. This dismissal of rigid, established military patterns is central to Dayan’s approach to strategy development throughout his career. The chapter then explores Dayan’s unique approach to strategy development, which was characterized by contextualized learning, the application of the 80:20 principle for setting priorities, delegation and empowerment, time management for maximum flexibility, and the use of meetings to generate and test new ideas. Dayan’s ability to hold two opposing points of view simultaneously and his love for the land of Israel are also discussed. Overall, the chapter offers valuable insights into the development of a strategist and the importance of context-specific thinking and flexibility in strategy development.