This article examines the importance of doubt in Western philosophy, with particular attention to the work of Søren Kierkegaard and Miguel de Unamuno. Kierkegaard's pseudonymous author Johannes Climacus ventures down the pathway of doubt, finds it perplexing and difficult and discovers that he is unable to return to his pre-doubting self. In despair, the meaningfulness of his life is called into question. Unamuno, a great admirer of Kierkegaard, acknowledges the suffering that accompanies doubt while affirming the pivotal role of uncertainty, despair and struggle in realising our humanity. From Unamuno, we can acquire a keener sense of the part education has to play in both forming us as doubting beings and allowing us to work constructively with the despair engendered by this formation.