In the fall of 2015, Jonathan Howland interviewed about a dozen independent school heads to inquire about novel programs and developments in their schools that, if they take root and flourish, could be "game changing"; about their vision of independent schools 40 years hence, in mid-21st-century America; and about impediments to reaching this vision. Among those interviewed were Emily Jones of The Putney School (Vermont), Andrew Vadnais of South Kent School (Connecticut), Kate Windsor of Miss Porter's School (Connecticut), Jim Scott of Punahou School (Hawai'i), Eric Temple of Lick-Wilmerding High School (California), Mo Copeland of Oregon Episcopal School (Oregon), Peter Hutton of Beaver Country Day (Massachusetts), Mark Salkind of The Urban School of San Francisco (California), Matt Glendinning of Moses Brown School (Rhode Island), Russell Shaw of Georgetown Day School (Washington, DC), and Kim Wargo formerly of The Hockaday School (Texas). In this article, Howland cites responses from these current or recent heads of schools and based on their responses, he concludes that independent schools that thrived in the last century embodied the virtues of self-examination, ambition, and judicious planning. These may no longer be sufficient. New cultural markers will include the capacity to be nimble and adaptable, and to experience innovation and change not as "countercultural" measures or "disruptive" threats but rather as endemic practices in every corner of the campus.