Private Sessions

Jim flew helicopters for a living for 57 years, 27 of them as a military pilot and 30 more as a civilian air rescue pilot running emergency medical, search and rescue, and law enforcement missions. Every one of those flights ran on the same rule: if an order came down and it was not clear to him, he...

Alex has been told her whole life that she starts a hundred things and never finishes any of them. Her husband named a room in their house Hobby Corner. She is also a CPA and a financial advisor with her own practice, three children under six, and a profession built entirely on systems and checklist...

George spent more than a decade editing for big companies like Meta and the NFL, and every time he landed the dream job it burned him out. So he left Los Angeles, moved to Texas, had a daughter, and started his own podcast agency to build a calmer, more predictable life. So why does someone who is w...

Katie grew up in a house of journalists. As an Answer Authority, she also asks a million questions, naturally needing to know everything. Now she produces live TV, and the hardest moment of her day is the one where somebody wants an answer before she has had time to find the right one. Breaking news...

Raymond plans everything. He is an elementary school teacher, the rock for his students and his family, and for years he has quietly wondered whether the thing that makes him steady is actually holding him back. He is rarely spontaneous, and he has started to think of that as a flaw. So why does som...

Eric sells pens to astronauts, leads a sales team, and is currently competing on a national game show. But every big idea he starts dies at the same point (what he calls hour 4) and he has spent years reading that as a lack of motivation. So why does someone this driven keep abandoning his best work...

Ava is a college student killing it on the debate team and eyeing law school, but she puts everything off until the last minute, and she has been told her whole life that it is a flaw. She’s majoring in national security and intelligence, the one who takes over every group project and wrote a 20,000...

Jenna Cooper has more ideas than she can finish — and no one's told her that's okay. She's chief of staff at a large state health agency, mom to a 5- and 2-year-old, and on her own time she's launched a block-level neighborhood organizing effort: potlucks, yard sales, cleanups, the whole thing. But ...

Tron Smith is thriving on paper, but she's quietly battling imposter syndrome. She works at Airbnb, runs her own rental staging company on the side, and her coworkers call her Professor Tron. So why does someone this capable still doubt herself? In this Private Session, David Kolbe (CEO of Kolbe Cor...