Freedom to Learn: Kathleen O’Toole on Classical Education, AI, & Rescuing a Lost Generation

In this episode of Freedom to Learn, host Ginny Gentles welcomes Dr. Kathleen O'Toole, associate vice president for K-12 education at Hillsdale College, to discuss the growing classical education movement as a transformative solution to what she calls the 'lost generation'—students struggling with focus, reading comprehension, and intellectual agility. O'Toole traces the crisis to systemic failures in education, including the abandonment of phonics instruction, the overreliance on technology from an early age, and a diminished vision of teaching as soul-forming rather than mere information delivery. She argues that classical education, with its emphasis on memorization, rich content, and the trivium (grammar, logic, rhetoric), restores intellectual depth and cultivates curiosity, imagination, and critical thinking. Drawing on her experience founding a classical charter school and leading Hillsdale’s K-12 network, O'Toole highlights how classical schools foster energized students, involved families, and a shared intellectual life centered on enduring works of literature, history, and philosophy. She also offers a hopeful vision for the future, asserting that classical education equips students with the cognitive resilience and self-directed learning skills essential in an age of AI, where human thinking and judgment will be more valuable than ever. The episode concludes with a call to action for parents and educators to reclaim education as a moral and intellectual project.