This article studies the implications of current attempts by organizations to adapt to a world of constant change by introducing the notion of playful organizational membership. To this end we conduct a brief semantic history of organizational play and argue that when organizations play, employees are expected to engage in playful exploration of alternative selves. Drawing on Niklas Luhmann's theory of time and decision-making and Gregory Bateson's theory of play, the article analyses three empirical examples of how games play with conceptions of time. We explore how games represent an organizational desire to reach out - not just to the future - but to futures beyond the future presently imaginable. The article concludes that playful membership is membership through which employees are expected to develop a surplus of potential identities and continuously cross boundaries between real and virtual social worlds.