Everyone talks about the benefits of playfulness for learning and development. But what do we do to become playful? What helps or hinders us on that road? And what is it like to stay on that road? If we can map out the path, including its obstacles and its benefits, it will be easier to create the circumstances under which children all of us can benefit from play. We might also better understand why and when attempts to become playful misfire, those moments when we see a chance to play and get creative, but it does not work out. We can come to see that this probably happens because one or more of the stepping stones is missing. Our research has identified four stepping stones that seem essential to becoming playful: autonomy, absorbed interaction, surprise, and feeling competent. First, individuals at play need to feel autonomous. The choice about what …