Oliver Herring, the creator of TASK, defines it as: "[a]n improvisational event with a simple structure and very few rules... TASK's open-ended, participatory structure creates almost unlimited opportunities for a group of people to interact with one another and their environment. TASK's flow and momentum depend on the tasks written and interpreted by its participants. In theory anything becomes possible." TASK invites participants to experiment, to improvise, and to play. The role of play as an important learning experience for children has roots dating back into the early 20th century (Groos, 1901; Severance, 1919; Dewey, 1934). In recent years, there has been a renewed interest by education scholars of 21st-century skills who have addressed the importance of play in education (Gray, 2013; Gude, 2010; Jones & Reynolds, 2011; Matta, 2013); in creative problem solving (Pitri, 2001), in embracing imaginative possibilities (Deleon, 2011), and as a way to access genuine student engagements that help to "revise and enlarge understandings" (Matta & Hostetler, 2003). One especially potent audience for TASK in the recent past has been educators and their students. Herring's work with involved educators involved with TASK facilitates an open dialogue to help the participants consider the importance of creativity in every discipline, not only the arts. He encourages teachers to recognize the crucial role and influence that they can have by enacting creative, open-ended student engagements in their schools. This article is about the author's experience of using TASK with his high school students.