Chris Cleveland, Head of School at Wesleyan, looks back on the worst advice he ever got: “Do what makes you happy.”

On the surface, it sounds harmless—even good. But in this episode of The Worst Advice I Ever Got, Chris explains how chasing happiness alone can lead to shallow choices, and why purpose, responsibility, and faith create something deeper and more sustaining.

It’s an honest conversation about leadership, values, and the difference between living for happiness and living for meaning.