Taking advantage of the possibilities for learning outside of school requires us to build on what we know about why it is so hard to sustain and scale up unconventional educational experiences within conventional schools. To illustrate the opportunities and challenges, Thomas Hatch describes a large-scale approach to project-based learning developed in a camp in New Hampshire and incorporated in a Brooklyn school, a trip-based program in Detroit, and Singapore's systemic embrace of learning outside school. By understanding the conditions that can sustain alternative instructional practices, educators can find places to challenge the boundaries of schooling and create visions of the possible that exceed current constraints.