Episode 10 Lilly Boron; From Off-Grid Alaska To The Superintendent’s Office episode artwork

EPISODE · Jan 29, 2026 · 2H 34M

Episode 10 Lilly Boron; From Off-Grid Alaska To The Superintendent’s Office

from Doug Has Questions · host Douglas

Send us Fan MailA World War II tent. A Yamaha piano hauled off a swaying dock. Five bears on the playground. A cancer diagnosis delivered in a plastic-lined hallway. And a small town that kept showing up. This conversation with superintendent Lilly Boron is a sweeping, human story about grit, grace, and what schools must become to truly serve kids today.We start with Lilly’s off-grid childhood in coastal Alaska—hauling water, tracking tides, and learning classical guitar in a homestead cabin. She grew into a teacher who could also rebuild servers, write databases, teach Spanish one chapter ahead, and turn a culinary class into a thriving, student-run kitchen. Then life swerved: breast cancer forced a reckoning that later shaped her leadership through COVID, the Beach Road slide, and community-wide grief. She opens up about the day she became principal as the state shut down, the “honk joyfully” recess plan to clear bears, and the daily staff circles that steadied people through loss.From there we dig into the big questions of modern education. What do we teach when Google knows everything? Lily argues for adaptability, stewardship, critical reading, and real connection as core outcomes—especially in a world warped by social media and AI. We talk neuroscience, dopamine loops, and why a tighter phone policy can actually make students happier. We unpack staffing churn, culture-building, and the difference between belonging and ownership. And we reflect on how schools can be the place where joy multiplies and grief is halved.If you care about student wellbeing, teacher support, or how communities stay whole in hard times, this one will stay with you. Follow, share with a friend who loves education done right, and leave a review with the one idea you’d bring to your local school.

Send us Fan Mail A World War II tent. A Yamaha piano hauled off a swaying dock. Five bears on the playground. A cancer diagnosis delivered in a plastic-lined hallway. And a small town that kept showing up. This conversation with superintendent Lilly Boron is a sweeping, human story about grit, grace, and what schools must become to truly serve kids today. We start with Lilly’s off-grid childhood in coastal Alaska—hauling water, tracking tides, and learning classical guitar in a homestead cab...

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Episode 10 Lilly Boron; From Off-Grid Alaska To The Superintendent’s Office

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This episode was published on January 29, 2026.

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Send us Fan MailA World War II tent. A Yamaha piano hauled off a swaying dock. Five bears on the playground. A cancer diagnosis delivered in a plastic-lined hallway. And a small town that kept showing up. This conversation with superintendent Lilly...

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