This article describes what happened when a group of middle school teacherresearchers at the International School of Billund (ISB), Denmark, joined university-based researchers from the Harvard Graduate School of Education, to engage in a new qualitative methodology called “Playful Participatory Research” or PPR (Baker & Davila 2018; Baker et al. 2016). The goal of the inquiry was to explore some of the tensions that exist between play and school—in particular the paradox between the timeless nature of play and the timetabled nature of school. The experiment was an example of one of the principles of a pedagogy of play proposed by the research team, which suggests that teachers’ collective and systematic study of artifacts of student learning (or “pedagogical documentation”) helps them to navigate such paradoxes. The teachers decided to replace two weeks of the standard school schedule with a ‘student-composed schedule’, in which students were free to design their own programme. Although the experiment got off to a shaky start, as it progressed, many students capitalized on the opportunity to choose where and with whom to work; they began to see each other as intellectual resources; and they started to take more responsibility for their own learning.