This chapter explores the issues related to both maps and mapping in complex and unpredictable terrains. The point made was that the process of mapping, as opposed to blindly following a map, enables reasoning and adjustments to emerge so that corrections can facilitate improved performance and a more purposeful journey. Indeed, mapping and navigation provide the basis for a journey into less certain and less recognisable terrains, with a general goal or overarching purpose. Indeed, W. Rankin reasons that maps provide the means for governments to understand, manage and defend their territory, pointing out that during the two world wars maps were produced by the hundreds of millions. The map-territory relation refers to the association between the map, as the representational output of the mapping process, and the object being studied, or the actual, physical territory. A map is not the territory it represents, but, if correct, it has a similar structure to the territory, which accounts for its usefulness.