Any activity that involves making choices entails the risk of failure, and the more personally meaningful the choices are, the more deeply felt the failure will be. Drawing on my experiences in supervising the self-chosen, long-term projects of my eighth-grade students, I argue that it is neither possible nor desirable to prevent young people from experiencing failure in a school context. Two narratives of student projects explore the potentially educative value of failure, for teachers as well as students. The article also explores the importance of providing young people with opportunities to make important decisions about their own schoolwork. As John Dewey observed, children cannot develop their powers of judgment except through the exercise of judgment. The moral, cultural, economic, and civic aims of education require that students become powerful agents in their own lives, and for this we need them to be able to consult their own values, develop their own goals, risk real failures, and take responsibility for the results of their actions.