As frustrating as failure may be, failing is an integral part of both playing and learning. As framed by Jesper Juul, failure is also a prime motivator for experiment and experience. How, though, can we best utilize that motivating quality of failure in disparate learning environments? This presentation seeks to interrogate failure as a form of progression, a forced consideration of strategy, process, and approach, and from different angles of analysis and praxis, attempts to share insights not on the art, but the utility, of failure.