Co-presented with Jerri Thompson, Head of School, St. George's Episcopal School and Paige Oliverio, Principal Designer, Urban Patchwork (urbanpatchwork.com).Building Outdoor Learning Environments (OLE) and risky play facilities are often associated with obstacles, both perceived and real. We explore some of the common barriers to planning, fundraising, building and maintaining these facilities through the lens of a 10-year-plan to remake St. George's into a natural haven for early-childhood education.