The language of self-belief, including terms like shyness and diffidence, is complex and puzzling. The idea of self-esteem in particular, which has been given fresh currency by recent interest in "personalized learning", continues to create problems. I argue first that we need a "thicker" and more subtle moral psychology of self-belief; and, secondly, that there is a radical instability in the ideas and concepts in this area, an instability to which justice needs to be done. I suggest that aspects of deconstruction are helpful here, and offer a reconstructive reading of Kipling's poem, "If"--, in order to illustrate the power of literature and a certain kind of philosophy to destabilize and resist closure.