This study examines the effects of a role-play-based pedagogical method in Finland on the twenty-first century skills propensity among 6th graders (12-year-olds). The approach entails a simulation of a society in a gamified learning environment as part of their formal education. Structural Equation Modeling was employed to analyze the students' (N = 253) self-reported effects of role-play experience on pre-and post-scores of twenty-first century skills propensity. The results show a statistically significant positive relation between holistic role-play experience and twenty-first century skills propensity, however, closer exploration reveals only few key associations, which perhaps illustrates the complex nature of both role-playing and the framework of twenty-first century learning. However, the broader positive view demonstrates the potential of one meaningful playful day for the skill and attitude development of young students as part of a formal curriculum.