The educational accountability movement in the United States under No Child Left Behind has negatively affected urban teachers because of high-stakes testing, narrowed curriculum, and scripted pedagogy. Such conditions have led to teacher stress, burnout, and attrition. Missing from the scholarly literature are the ways in which teachers work to overcome these conditions. This article offers a self-study that examines an urban elementary teacher’s journey as he navigated both within and against the structural mandates of No Child Left Behind. Using Anthony Giddens’s theory of structuration, the author elaborates on four key factors—strong teacher preparation, cultivation of caring relationships with students and families, collaboration with other teachers, and development of an informal contract with administration—that ultimately were responsible for his success and well-being