Every organization has some degree of “chaotic” culture. Some of them breed chaos and unconsciously operate in chaos. Project management is designed to operate with structure. However, reality has always contained a dose of “Wonderland” as well. Projects find themselves at odds with the environment that they operate within when the underlying organizational culture tends to be chaotic and less disciplinary and operates randomly. Project management methodologies and execution processes’ logic and convention are contradicted by the chaotic, shape-shifting setting of “Wonderland.” This conflict threatens a successful outcome for a project. The uncertainty that projects are confronted with throughout the execution process can be fatal. Chaos, by its very nature, is impossible to control completely, and so projects struggle to deliver as they fail to manage the conflict they find themselves in with the organization’s way of life.