When the No Child Left Behind Act became law in 2002, its intent was to ensure that all students at all public schools throughout the United States receive the same quality education regardless of race, gender, or socio-economic background. However, because of the law’s heavy-handed, top-down measures, it has failed to help the very population it was allegedly meant to aid, the at-risk student. Being Sisyphus examines at-risk students at a community day school in Southern California. It argues that such schools must be encouraged to draft and their own on-site behavioral standards before any consideration can be given to teaching academic standards meaningfully. Once behavioral standards have been successfully implemented, the academic focus should be placed upon literacy instruction. Texts of all varieties should be used as vehicles to challenge and expand the at-risk student’s worldview, and writing should be employed across the curriculum as their chief means of demonstrating what they have learned. In the end, the work is a constant struggle, one that the mythic Sisyphus would surely recognize and appreciate.