This essay focuses on the value of self-doubt in moral inquiry and in moral education. Using John Patrick Shanley’s play, Doubt: A parable, as illustration, it shows how self-doubt initiates and extends moral inquiry, highlights one’s epistemic fallibility and connects the inquirer to the virtue of humility. The essay draws on the work of Charles Sanders Peirce, Hullett, Nussbaum, Thayer-Bacon and Elbow to support the idea that the question ‘Am I wrong?’ is important for moral inquiry and for moral education.