This study focused on the digital design practices of Raul, a 15-year-old participant at a summer video game design camp for adolescents. As Raul developed his original game, "You Will Perish," I wondered what his design process might reveal about (a) the practice of affectively and procedurally literate video game design and (b) the literacy pedagogies that can support such design. Guided by the concept of serendipity, I describe Raul's design practice as an open process characterized by bouts of failure, chance, and discovery, and I examine how such forces shaped the emergence of his game. Using transversal analysis, I trace Raul's design through an account of frustration and failure, perseverance and pride, showing how the challenges of the game's creator become those of the game's players. The study highlights the generative potential of serendipitous literacies wherever and whenever literacy happens.