Tim O'Brien's "The Things They Carried" is an example of what the author calls a narrative of failure. A narrative of failure is a term for a narrative that both fails in the enactment of its own telling and that takes failure or failing as one of its subjects. This paper discusses how, as a form for telling a teaching story, narratives of failure can be remarkably productive because they suggest alternative values--values like comprehensiveness and seriality, values that resist and elide the heavy-handedness of an educational apparatus and that draw attention to their own institutional, disciplinary, or methodological constitution. By doing so, they continually force us to ask questions about power and desire, about processes of making knowledge, processes at the heart of schooling and teaching. These questions should be at the heart of schooling as they are at the heart of Tim O'Brien's storytelling. By blending content and context, O'Brien illustrates that knowledge cannot be separated from the knower. In such circumstances, one is obligated to ask what is both lost and gained in the process, to ask in whose name and in what interests is knowledge made, and to ask who benefits and who concedes. The notion of failure saturates teacher work. Teachers hold, within the profession, to traditional notions of success that necessarily leave their practices lacking. According to these definitions, all teachers can do as teachers is fail. Even so, that kind of failure more accurately represents the work of teaching and the process of understanding at work; failure is foundational to the nature of what it means to teach. Teachers ought not dwell on their lack of conventional success but rather teach in order to teach again. Reiteration is not a sign of lack of success but a hallmark of the teacher's work. This is one lesson an attentive reader understands from Tim O'Brien.