Abstract
This chapter begins with conversations in a prison on Samuel Beckett and pedagogy, conversations that emerged from the authors classes in philosophy. There are two interwoven strands in the chapter. One questions the emphasis on competition and achievement in contemporary education and its implications for the author's relationship to failure. The second, strongly influenced by Beckett, explores ways of reimagining the relationship to failure in such a way that allows them to reflect on what matters in life. Rather than seeking to eliminate failure, it is more interesting to think about how the concept of failure could be reimagined if, as Beckett suggests, failure is not accompanied by disappointment but became simply what we do, rather than being something we are.