With the active generation increasingly thinking visually, creating meaningful maps is paramount to the whole of the military operational art, defined as the arrangement of tactical actions in space, time and purpose in the pursuit of strategic objectives (Army Doctrine Publication [ADP] 3-0, 2011). The challenge lies in understanding how meaning is created and shared, not just within our own communities, with our dominant mental models, but also from the perspectives of whole-of-government efforts, our coalition partners, and especially our rivals. Inspired by Discursive Maps at the Edge of Chaos (Primeau, 2017), this paper will leverage the thought processes of two major war theorists since the Enlightenment; Antoine de Jomini and Carl Von Clausewitz, to illustrate the nature of meaningful maps. It will then use philosophy and complex social systems theory to emphasize how we invariably all see the world differently, based on our identity. The result is an argument that most maps fail the operational artist, but that by applying good design methods we can improve on their meaning.