This is the story of educational outreach at the Santa Fe Institute: how we began with a grand vision, thudded back to earth, and then – through doggedness, windfall opportunities, an unanticipated digital revolution, and sheer luck – coaxed a program to emerge that is surprisingly resonant of the original idea. The conversations among SFI’s founders in the early 1980s envisioned SFI on a Rockefeller University model – a research institute offering accredited graduate education. “Teaching would be accomplished mostly in seminars and short series of lectures, but, above all, by means of apprenticeship and research,” wrote Murray Gell-Mann in “Emerging Syntheses in Science,” the volume memorializing the Institute’s founding workshops. At the time, Gell-Mann estimated that “three units” (a unit being $100 million) would be sufficient as an endowment to get the Institute off the ground. Unfortunately, such monies were not forthcoming. The research program would begin, but a student campus would have to wait. Further, the administrative hurdles of the accreditation process loomed larger than anticipated. Without specific funds for outreach or prospects for a campus, with no apparent legitimacy, and without obvious access to students (only a few of the Institute’s founders were at universities), SFI’s original Big Plan for education soon needed a reset. Despite these logistical obstacles, George Cowan and his founding colleagues had some strong intangibles in their favor. Most important, they had a clear mission; scholarship would focus on the transdisciplinary study of complexity, a concept that provided a broad canopy for exploring various systems.