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A decorated high school art teacher walks away from the system—and finds a bigger canvas. Jessica Chivon joins us to share how she traded classroom constraints for a studio-first life, why students are hungry for handwriting and analog craft, and how sketchbooks can quietly reveal anxiety, resilience, and hope. Her story threads personal transformation with a larger cultural shift toward authenticity in an age of AI and instant everything.

We dig into the tensions inside modern education: AP-heavy schedules that sideline creative courses, permission-slip politics around museum nudes, and the chilling effect of censorship on curious minds. Jessica makes a compelling case that art has always been a grassroots technology—pen, paper, and an idea are enough to move people—and that’s exactly why it gets squeezed. From Shepard Fairey’s Hope poster to Norman Rockwell’s late civil rights works, we explore how images carry social change. She also spotlights Kehinde Wiley’s portraits and sculptures, which center Black subjects in heroic, Renaissance-inspired frames, reframing who belongs on the wall and why representation matters.

COVID turned out to be an unexpected studio residency. With document cameras and livestreams, Jessica discovered that adults crave real instruction without the commute, and that kindness plus clear steps can turn “I can’t draw” into daily practice. She’s building an online school rooted in community, modeling a path many creatives quietly consider: use tech to teach, keep the work human, and let the craft lead. If you care about arts education, mental health, and finding your creative voice amid noise, this conversation offers practical insight and a hopeful map forward.

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