"The Oxford English Dictionary" defines fulfilment as 'satisfaction or happiness as a result of fully developing one's potential or realizing one's aspirations; self-fulfillment'. Not only has the idea of fulfilment underpinned 'approximately twenty centuries of philosophy' as Lefebvre notes, it plays an indispensable role in both popular and scholarly accounts of education and upbringing. Experiences of education, of upbringing and of 'life lessons', however, are so often "not" about the fulfilment of oneself, about the discovery and actualisation of one's full potential. Such experiences instead involve moments of sometimes irreparable failure and loss--a matter that has not received a great deal of attention in educational research and theory. After briefly examining the way that fulfilment is favourably framed both in humanistic psychology and in neo-humanist "Bildungstheorie," this paper considers some of the exceptions to the nearly ubiquitous identification of education with fulfilment: Arthur Schopenhauer's view of the irrationality of human (developmental) experience and Ludwig Wittgenstein's use of the term 'conditioning' ("Abrichtung") in some of his accounts of learning and socialisation. We then focus on failure and loss in education through an overview of the pedagogical theory of O.F. Bollnow. Bollnow, as is gradually being recognised in English-language scholarship, saw moments of uncertainty, disorientation and above all crisis as indispensable in educational experience--for both student and teacher. In this way, we show that instead of being the pursuit of self-fulfilment, education is unavoidably a matter of difficulty, disruption and also failure. It reshapes us, and this reshaping can be seen as being as much about formation as it is about deformation.