Bankrupt and in the Hall of Fame the Same Year: How Leaders Climb Out of Crisis, with Jess Pettitt

"The same year that I filed bankruptcy, I was inducted into the Hall of Fame." Jess Pettitt

On Inauguration Day, my friend Jess Pettitt lost her largest contract. Not because of anything she did. The entire office she worked with was closed 21 minutes after the inauguration, and the people she'd been working with called her from the sidewalk, holding boxes of everything that had been on their desks. Then the state contracts went. Then the retainers. Twenty years of building a business, flipped in a minute. Bankruptcy. Depression. And in the middle of all of it, a call from the National Speakers Association: you're being inducted into the Hall of Fame.

This is not a highlight reel, and neither is her new book, Doing Good Better: Using Dysfunction as a Catalyst for Change.

In this episode, I sit down with Jess to talk about what really happens when everything falls apart at once, and why so many leaders end up burnt out and alone in it, convinced nobody can help them. We get into her five-stage climb for organizations in crisis, why most companies run on a story that's "reported up instead of verified across," the difference between planting a flag and hanging up decoration, and why the mess you're afraid of is already there. If you lead people, this is burnout prevention at the system level, not a pedicure.

Key Topics Covered:

What it's like to lose your largest contract 21 minutes into a new administration, and the wave of losses that followedFiling bankruptcy and being inducted into the Speaker Hall of Fame in the same year, and holding joy and tragedy at onceWhy your identity being tied to your work makes a professional crisis a personal oneThe leaders who believe "no one can help me," why they feel so alone, and why that loneliness is disempoweringInternal pressure vs. external pressure, and learning to function inside the pressure without doing it aloneWhy so many leadership books ignore the fact that leaders are humanThe climb: know your numbers, hold the line, earn the room, plant the flag, outlast the cycleHow organizations evolve into "a story that is reported up instead of verified across," and why no one is reading the quarterly reportThe CEO of 80,000 employees still running his company like it had four peopleCooperatition: why cooperating with your competition is how you actually earn the roomPlanting a flag vs. decoration: what Anthropic and Costco got right, and why a statement for your website isn't a valueWhy the mess is already there, and