In today's world we appear to place a premium on happiness. Happiness is often portrayed, directly or indirectly, as one of the key aims of education. To suggest that education is concerned with promoting unhappiness or even despair would, in many contexts, seem outlandish. This paper challenges these widely held views. Focusing on the work of the great Russian writer, Fyodor Dostoevsky, I argue that despair, the origins of which lie in our reflective consciousness, is a defining feature of human life. Education, I maintain, should not be seen as a flight from despair but as a process of deepening our understanding of suffering and its potentially pivotal role in our humanisation. In developing these ideas, I draw on Kierkegaard's "The Sickness Unto Death" and Unamuno's "The Tragic Sense of Life in Men and Nations", among other sources.