This chapter opens by laying out one of the central tenets of this book: that management is not about eliminating uncertainty, but about continuously engaging with it. In doing so, the chapter challenges the managerial illusion of control by showing how organizations of any size or maturity are inevitably exposed to dynamic environments that defy full predictability. The chapter develops the metaphor of the Unexpected Game, in which organizations must navigate through surprises that can either threaten their plans or open new avenues for value creation. Grounded in management theory, the chapter outlines two consistent principles of what I refer to as the Unexpected Game. First, uncertainty is a permanent and ubiquitous condition that no amount of planning can eliminate. Second, not all uncertainty is adversarial; some of it hides potential advantages that can be activated through human agency. These principles lead into a discussion of three distinct organizational phenomena (serendipity, zemblanity, and bahramdipity) that present firms with different ways of encountering the unexpected: as a source of generative possibility or as a trigger of avoidable failure. By framing these phenomena as partially inducible patterns, the chapter positions the book as both a theoretical contribution and a practical resource for managers and entrepreneurs seeking to understand and enhance how organizations engage with uncertainty.