The philosopher and educator John Dewey is often attributed with saying that “education is not preparation for life; it is life itself.” This is a complex statement about how education, every day, at every level, and for every student, should be intricately involved in and a part of real life and societal concerns. Dewey (1893) distinctly rejects the premise that school ought to sequester students from the life forces of society in order to build knowledge that will be integrated when students leave school and enter “real life.” We open our chapter with Dewey’s quote because it points to a philosophical and practical tension in schooling-its relationship to and staging of life readiness. We experience this tension when we hear students ask, “Why are we doing this?”; when we see curriculum goals broken down into seemingly isolated and unconnected skills; or when we encounter closed school and classroom doors as barriers between the school and its community. We think what students really seem to be asking is, “How is this connected to me and the real world?”