In 2012, senior fellow at the Martin Institute for Teaching Excellence Grant Lichtman visited dozens of schools and interviewed hundreds of educators about what they see as the future of learning and of schools and published his findings in "#EdJourney: A Roadmap to the Future of Education" (Jossey-Bass, 2014). Since then, he has been asked to share these findings with many independent school teams and independent school associations around the country. Through a series of design thinking-based workshops, he was able to gather, archive, and synthesize some of the additional questions and ideas generated by diverse groups of education-focused attendees. The findings raise interesting questions about the tension in schools between new ideas and past traditions. In total, approximately 1,700 members of the independent school community contributed to this knowledge base, including classroom teachers, business officers, heads of school, technologists, academic and nonacademic administrators, and a smaller number of students, parents, and trustees. Because regional independent school associations organized many of the workshops, the participants represent hundreds of different schools, of all kinds and sizes, from nearly every region of the country. By June 2014, Lichtman had gathered about 2,000 "What if" questions and started sorting them into what he believed to be "buckets" of similar ideas. Given absolutely no preconditions, more than 70 percent of these expansive ideas, representing all school stakeholders, fell into groupings that describe dramatic, sometimes radical changes to the fundamental structures of learning in schools. They posit major changes in how time is used; how educators work together; the nature of learning based around subject; how students are taught and assessed; and the role of students as the primary owners of the learning process. None of the top dozen categories of ideas is among those that frequently dominate traditional strategic plans: recruiting and compensating excellent faculty, building better facilities, increasing endowment, enhancing diversity, keeping up with technology, or developing the school's brand. This article presents the aggregate results of this crowd-sourced data and delves into the topics that formed the top 70 percent of these expansive "What if" questions and ideas.