This monograph addresses how humans think and make sense of the world, and whether the current logic used by the U.S. military is still useful for understanding and influencing a world where complexity continues to increase. Drawing from elements of organizational theory, general systems theory, political science, and post-modern philosophy, this monograph presents a logic model to explain how the military currently makes sense of the world, and how Design offers a different and potentially more useful approach to complex systems. Design represents a paradigm shift in thinking, and functions under an entirely distinct logic that conflicts with many elements of traditional military detailed planning. Many of the ongoing tensions within the military over how to incorporate Design into doctrine and practice reflect this monograph's thesis. Detailed planning logic is becoming increasingly problematic in making sense of the world in the 21st century when used alone. Design offers a novel and potentially more useful logic for the military, and many still relevant elements of detailed planning logic are useful for the military after integration with Design's overarching methodology. In order to apply Design, the military must first understand how it currently thinks about the world, and why that methodology proves problematic when dealing with complex systems. There are numerous elements within Design's unique logic that proves challenging for the military, as this monograph will explain in terms of vocabulary, institutional tenets, and the tensions concerning procedures and processes that fundamentally define military operations. Design alone is not a 'silver bullet' for the military and does not destroy detailed planning entirely; Design represents a distinct way of thinking and provides the military with new approaches to influencing an increasingly complex world.