146. Dr. Jason Van Heukelum's Passion for Multiple Choices

Listeners, buckle up. You’re about to meet a Virginia public school superintendent whose mother referred to him as Tom Sawyer, and for good reason. Dr. Jason Van Heukelum has been rallying people around bold visions since his earliest days in Rochester, New York. We can only imagine him convincing friends to join some backyard adventure, or today, getting entire communities to reimagine high school. Jason is someone who knows how to design and build—and bring others with him.

He’s also the kind of educator, coach, guide and mentor who sees transformation not as a someday ideal, but as a here-and-now imperative. His 27-year journey includes teaching math, coaching sports, leading middle and high schools, and directing an American international school in La Paz, Bolivia. He brings deep systems experience, from classroom to central office, and a rock-solid belief that the secret to great schools lies in pairing high expectations with a deep connection to community, where so much of learning happens.

Today, he’s the superintendent of Winchester Public Schools in Virginia and the driving force behind something extraordinary: the Emil and Grace Shihadeh Innovation Center, a cathedral to possibility and purpose that redefines what high school could be. No bells. Just young people walking through doors into real-world learning and a buffet of multiple choices.

But before we get there, we’re heading to Algonquin, Canada, where a young Jason portaged a canoe across miles of wilderness. We’ll linger in Ecclesiastes, the Old Testament book that moves him, even on the hardest days, to rejoice in the work and find meaning in the mystery. We’ll talk about "The Speed of Trust," why relationships drive change, and what Jason means when he says, “The most important lessons we learn cannot be measured by standardized tests.” We’ll dive into the Shihadeh Center, his strategic vision for Winchester, and how his grad school capstone is becoming real through collaborative, school-based services.

We’ll explore cathedral thinking, the future of public education, and the courage it takes to build innovation that lasts. And in the end, we’ll honor the wisdom of a mentor named Penny Hedrick, whose support Jason carries with him every day. To close these show notes I’ll quote from a letter written on Jason’s behalf: “The best leaders make everyone around them better. The best leaders improve the organization they lead, cultivate passionate and loyal followers who believe in their vision, and pave the way for future leaders to carry on their work when they are gone. Jason Van Heukelum is one of the best leaders I have had the opportunity to work with.”

Our episodes are edited by the talented audio engineer, Evan Kurohara. Our theme music comes from the catalog of pianist, Michael Sloan.