Failure is seen as a problem in education. From failing schools, to failing students to rankings of universities, literacy or numeracy, the perception that one has failed to compete or to compare favourably with others has led to a series of policy initiatives internationally designed to ensure ‘success for all’. But when success is measured in comparison with others or against benchmarks or standards, then it is impossible to see how all could be successful given the parameters laid down. What are the implications of a culture that values success and achievement? How difficult is it to become the kind of individual who is flourishing, autonomous and becomes ‘all she can be’, in particular under the precarious conditions of contemporary capitalism? Samuel Beckett was sceptical of the quest for progress, production and prestige. His philosophy invites another way of thinking about failure, not as something one is, but rather as something one does: the pain and fear of inadequacy that can mark educational relations and experiences is alleviated by a more renunciative, gentle philosophy of education. There are two interwoven strands in this article. One questions the emphasis on competition and achievement in contemporary education and explores its implications for our relationship to failure. The second, strongly influenced by Beckett, explores ways of reimagining our relationship to failure in such a way that allows us to reflect on what matters in life.