Military officials often utilize the PMESII-PT acronym (Political, Military, Economic, Social, Information, Infrastructure, Physical Environment, and Time) as an analytical start point to assess an operational environment. However, the linear methodology restricts a holistic understanding of fundamentally asymmetric realms where U.S. military leaders currently operate. Scholars and other experts have previously applied more ontologically based and holistic approaches to understand complex social systems. By comparing both PMESII-PT and these holistic approaches, this paper accomplishes three objectives. First, the monograph concludes that the linear PMESII-PT methodology is not sufficient to assess and convey understanding of a complex environment. Second, the monograph specifically identifies the incorporation of identity theory and the proper use of the narrative as the gap between PMESII-PT and holistic approaches. Finally, in light of accusations that the U.S. military still exhibits a lack of cultural understanding, this monograph presents a more conceptual start point for military designers. By applying a process of metaquestioning to explore the facets any complex environment, military designers can ultimately produce an identity-based narration which leads to a level of holistic understanding unachievable by traditional methods.