Noticing that I had developed a tendency to beat myself for failing to meet what I now know are rigid, uncompromising criteria for self-expression in school subjects such as drama and sport, I decided to throw myself into the world of boxing in a bid to recapture my confidence as preparation for university. What I found was very surprising: contra to what one might expect of a competitive boxing environment, failures were neither negated nor treated with hostility. Instead, failures were presented as something to be explored and discussed openly and critically as a means to self-reflection, acceptance and developing personal style – qualities I wrongly assumed would be encouraged at school and in academia. Drawing from my personal experience of education, boxing and what I consider as the valuable art of distraction, this paper suggests that we look again at the role of failure in pedagogy in order to address the narrow and sometimes stagnant guidelines we have developed within our learning cultures. In other words, I am suggesting that we position failure as a way to both confront and antagonise the notions and practices we have inherited for training bodies and minds to simply embody and repeat received knowledge from one generation to the next. Failure, I have found, can inspire alternative ways of collaboration, reflection and creative practice wherein acknowledging failure is essential for fighters/students to discover a freedom of expression that allows them to navigate and share their learning experiences with confidence and negotiate their environment on individual terms.