So far we have examined planning in complex systems in terms of both map-making and exploration of the new nonlinear geography. Both of these planning roles assume it is a rational process, consciously utilizing new constructs to better map and explore the new terrain that is being revealed. But the new geography emerging from complexity research is, in many respects, so unlike the predictable, linear, simple, and equilibrium-based world of classical science, that rationality itself is in need of revision. The point being made here is not a call to act irrationally, but, instead, it is to place attention on how reason itself has been shaped to conform to the linearity and simplicity of the classical world. In an environment that is, in important respects, unpredictable, unstable, and vulnerable to random events, then the rationality of planning must include new outlooks and practices congruent with the new world being discovered. Here, the appropriate image for planners may not so much be the rational designer as that mischievous figure from mythology: the Trickster. Found in diverse cultures throughout the world, the Trickster breaks taboos and flouts, traditional mores and norms, constantly investigating, improvising, and devising new ways (Harding, 1963). The pranks of Trickster figures are legendary and surprisingly similar to the characteristics of complex, nonlinear systems: unpredictable; bizarre; disproportionate; random; mixing-thing up; stirring the pot; upsetting the apple-cart. These qualities are certainly a long way from the image of planning as precise forecasting, conscious design, and careful implementation of strategy. Yet, it may be that it is these tricks of the Trickster that organizations desperately need to navigate through these tumultuous times.