The recent strategic failures in Iraq and Afghanistan for military coalitions illustrate that we have significant problems with understanding how and why we plan military campaigns in ways that over time demonstrate ineffectiveness and confusion. Arguably, we may not realize why we construct insufficient campaign plans because we are not even aware of our cognitive behaviors. This article critically charges that our entire approach to understanding conflict and our subsequent military planning methodologies stem from highly limited yet deeply cherished conceptual models that operate behind the scenes. We hardly realize them, yet they dominate our very understanding of how we imagine the world functions. With military campaign plans, our centralized hierarchies, linear causality reasoning, and other significant sociological forces send us into cycles of poor planning along with institutional blinders that resist critical reflection on why we are failing.