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Uber, the virtual service that connects drivers to passenger, presents a novel form of work-organization in which managerial functions are transposed into a virtual platform. This ethnographic study documents how Uber drivers in the city of Monterrey, Mexico navigate and come to make sense of the Uber model of work. Employing the conceptual device of the work-game, this study argues that engagement in the game of “earning coins” coupled the interest of drivers in generating the most-possible income with the interest of management in maintaining a readily available labor pool. Reinforcing this coupling was Uber’s deployment of an entrepreneurial ideology of “being your own boss,” which was especially important given the company’s lack of a physical management structure. However, as Uber takes advantage of the deindustrialization that has gripped Monterey, it attracts drivers exhibiting varied employment trajectories. This in turn creates different modes of playing the work-game and thus generates sharply divergent subjective understandings of the work, whose nature this chapter explores.