Have you ever stayed somewhere so long that leaving—even when you know you’re ready—feels completely terrifying?
Yeah... this week, Jessie did it.
After 14 years with the same state agency and nearly 20 years working in government, Jessie has officially quit her job, left the public sector, and started an entirely new chapter.
And naturally, we have a LOT to talk about.
This week, Jessie and Kiki get into what it actually feels like to leave a career that has been part of your identity for decades: interviewing for a private-sector job while on beach vacation, secretly navigating the hiring process while recording podcast episodes, saying goodbye to longtime coworkers, driving away from the office for the last time, and adjusting to a completely different work culture.
There are some things Jessie misses already...
There are other things she absolutely does not... Like commuting into Atlanta. Traveling across the state for a 15-minute meeting. Answering work calls after hours. And apparently spending approximately half her life in meetings that absolutely could have been emails.
But this isn't just a career-change episode.
Because before Jessie can get too reflective, Kiki and Professor Binky drag us into TV “This or That,” where we debate Sex and the City vs. Gossip Girl, Ted Lasso vs. Schitt’s Creek, The Crown vs. Downton Abbey, The Office vs. Parks and Recreation, and whether Jessie has officially betrayed Gilmore Girls.
Then Jessie introduces a game called DCA or NBC: Did this completely unhinged workplace scenario actually happen during her years in state government… or is it a storyline from The Office or Parks and Recreation?
And, frankly, the real stories may be worse.
You truly cannot make this shit up.
But underneath all of the workplace chaos is a conversation we've been circling around for months: How do you know when it's finally time to leave?
Jessie talks about realizing that career success doesn't mean the same thing to her at 43 that it did years ago, how COVID changed her priorities, what it feels like to finally have boundaries around work, and why being valued and supported matters more than any title.
And one week into the new job? She feels lighter.
In this episode:
- Making a major career change in your 40s
- Interviewing for a new job while on vacation
- The emotional weirdness of your final week at work
- Working remotely full-time
- Adjusting to real work-life boundaries
- Career burnout and redefining success
- DCA or NBC: workplace stories that should absolutely be fictional
- Revenge drug tests
- Parking-deck arson
- Government office naps
- And why “You Can’t Make This Sh*t Up” may be the perfect title for an entire career
Sometimes starting over doesn't mean everything before it was a mistake. Sometimes it just means you finally realized you're allowed to choose something different.
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