"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 followed
- Filing bankruptcy and being inducted into the Speaker Hall of Fame in the same year, and holding joy and tragedy at once
- Why your identity being tied to your work makes a professional crisis a personal one
- The leaders who believe "no one can help me," why they feel so alone, and why that loneliness is disempowering
- Internal pressure vs. external pressure, and learning to function inside the pressure without doing it alone
- Why so many leadership books ignore the fact that leaders are human
- The climb: know your numbers, hold the line, earn the room, plant the flag, outlast the cycle
- How organizations evolve into "a story that is reported up instead of verified across," and why no one is reading the quarterly report
- The CEO of 80,000 employees still running his company like it had four people
- Cooperatition: why cooperating with your competition is how you actually earn the room
- Planting a flag vs. decoration: what Anthropic and Costco got right, and why a statement for your website isn't a value
- Why the mess is already there, and why recognizing it is the hardest (and most important) step
Quotes:
"The same year that I filed bankruptcy, I was inducted into the Hall of Fame as a lifetime achievement for the 20 years of work." (13:42 | Jess Pettitt)
"Loneliness is disempowering." (20:19 | Jess Pettitt)
"Not to relieve the pressure, but to function inside the pressure, not alone. Now we can get somewhere." (22:28 | Jess Pettitt)
"So many leadership books are written in a way that ignores the fact that leaders are human." (22:50 | Cait Donovan)
"No one is reading that report. But above that, no one read it. No one knows anything because no one read it." (35:50 | Jess Pettitt)
"That's not planting a flag. That's decoration. I don't do decorations." (52:58 | Jess Pettitt)
"You are in a mess that you either do or don't acknowledge. You're not searching for a mess. It's already there." (55:56 | Jess Pettitt)
In this episode, we mentioned...
Doing Good Better: Using Dysfunction as a Catalyst for Change, by Jessica Pettitt
Good Enough Now, by Jessica Pettitt
Mismatch: Why Good People Burn Out in Good Organizations, by Cait Donovan (out October 27, 2026)
The National Speakers Association and the Speaker Hall of Fame
Maslow's hierarchy of needs
How a Leader's Ego Can Burn Out Their Team with Ewa Błaszczak (FRIED #362): https://redcircle.com/shows/e4c0db0a-98a4-47e6-a2b0-6a291469e1d6/episodes/b700a7df-0551-43c9-a090-8dbf1c7d235f
Your Team Already Knows You're Burnt Out: Leadership, Capacity and the Busy Badge, with Anton Gunn (FRIED #366): https://redcircle.com/shows/e4c0db0a-98a4-47e6-a2b0-6a291469e1d6/episodes/bf0988c2-d195-4618-8bd0-3b0f86c956fb
Daisy Auger-Dominguez: Burnt Out Leaders Lead Burnt Out Teams (FRIED, Sep 2024): https://redcircle.com/shows/e4c0db0a-98a4-47e6-a2b0-6a291469e1d6/episodes/ffa7b9d6-0632-4b0f-bb12-0960a7c04459
#straightfromcait: How to Ask for Help (FRIED #10): https://redcircle.com/shows/e4c0db0a-98a4-47e6-a2b0-6a291469e1d6/episodes/6a6bd8f1-6666-4018-97d5-a73c4545a75d
Connect with Jess Pettitt
Jess Pettitt, CSP, CPAE, is a leadership and crisis communications keynote speaker and advisor. She started out as a university administrator by day and a stand-up comic by night in New York City's comedy clubs, and spent 20+ years doing diversity, equity and inclusion work with more than 1,400 organizations and half a million audience members. In 2026 she was inducted into the National Speakers Association's Speaker Hall of Fame. Her newest book, Doing Good Better, is a no-fluff guide for leaders who sense a crisis, are in one, or might be the crisis.
Take the 6-question advisory survey: https://jesspettitt.com/advisory-survey
Website: https://jesspettitt.com
Book: Doing Good Better: Using Dysfunction as a Catalyst for Change
Connect with Cait
Book Cait to speak: https://bit.ly/bookcait
Watch the 3-min sizzle reel: https://bit.ly/caitdreel2025
Order Mismatch for your team (bulk copies): annick@caitdonovan.com
LinkedIn: https://linkedin.com/in/caitdonovanspeaks
Instagram: https://instagram.com/caitdonovanspeaks
If you work in HR, People and Culture, or you book speakers for leaders who are carrying more than anyone can see, this is for you.
About the Host
Cait Donovan is a burnout expert, keynote speaker, and host of FRIED. The Burnout Podcast, a top 1% global show with over 1 million downloads and 360+ episodes, ending burnout culture since 2019. With a background in biobehavioral sciences and Traditional Chinese Medicine, she helps organizations find the mismatch behind burnout instead of blaming the people inside it. She is the author of The Bouncebackability Factor and Mismatch: Why Good People Burn Out in Good Organizations.
