Tom DeLong

Tom DeLong spent decades at Harvard Business School teaching some of the most driven leaders in the world. In this conversation, he unpacks what he calls the high achiever's paradox: the more you accomplish, the harder it gets to feel like it's enough. We talk about the quiet identity crisis that hits mid-career, why the usual playbook (bigger title, bigger deal, bigger platform) stops working, and what a real next chapter looks like when you're no longer trying to prove anything.