While demonstrating how The Tempest’s magic island serves as an artificial training environment, this essay draws on diverse examples and critiques of neo-liberalism’s gamified work-life to query the relation between the challenges that the play’s characters face and the social roles they are primed to occupy. In the histories of the Bermuda wreck that inspired The Tempest, the sheltered climate and collective endeavor that “seasoned” colonists for the New World were treated as a wonder and a miracle. But this felicity is unsettled by the limited capacity for optimization that the play assigns to certain character types. The Tempest’s regime of gamification is therefore a means of constituting capitalism’s “civilizing” mission as well as a resource for accosting the flaws in that nascent regime.