Josh Harris with John Crossman on "Career Halftime" Why Your Best Years Might Still Be Ahead. (S4E29)
The Crossman Conversation: CEO Edition
Saturday, July 18, 2026 - 28 minutes
On this episode of The CEO Edition, host John Crossman sits down with his frequent guest Dr. Josh Harris for a rare, personal conversation about what he calls "halftime" — that midpoint moment when a career is established but the biggest opportunities may still be ahead. John draws out Harris's honest admission that his path, including an unplanned decision to pursue a PhD during the 2008 financial crisis, has been a genuine grind rather than a smooth ascent. Harris opens up about imposter syndrome, losing his father, and the discipline of ongoing coaching, while Crossman reflects on his own perspective from the far side of "halftime." It's an unusually candid conversation about resilience, humility, and staying curious no matter how credentialed you become.
