Digital games have become popular for engaging students in a range of learning goals, both in the classroom and the after-school space. In this article, I discuss a specific genre of video game, the massively multiplayer online role-playing game (MMO), which has been identified as a dynamic environment for encountering 21st-century workplace skills (King, 2012). Rather than advocating for bringing MMOs directly into the classroom to deliver content, I focus on designing after-school programs. Starting with a description of the MMO, I define the game space as a digital platform where an array of interest-driven learning takes place. Then, based upon a 2-year, game-based after-school program for teenage boys, the Casual Learning Lab was designed (Steinkuehler & King, 2009). Finally, I offer suggestions for program design highlighting the importance of involving teachers as co-learners, and structuring reflection activities to assist participants in connecting gaming activities to 21st-century skills.