“The power of play.” We hear a lot in educational circles about how play embodies risk-taking, experimentation, and exploration. It is a very powerful way to learn. Plus, it’s fun! Who doesn’t like play, right? But play can be tough to implement in the typical classroom tasked to raise test scores, adhere to a vetted teaching scope and sequence, and prepare learners for productive livelihoods in the context of an uncertain economy. This is the story of two colleagues who saw a playful friendship turn into a fruitful professional collaboration.