The Career Flipper Podcast
Career change stories from everyday people to inspire you on your own career path.
For Anyone Rethinking Work, Identity & What Comes Next
The Career Flipper Podcast is a collection of honest, evergreen conversations with people from around the world who have changed — or flipped — their careers.
Created after a tech layoff and a long season job searching and no longer fitting where I once did, the podcast explores what happens when the path you planned no longer makes sense, and you’re brave enough to imagine something new.
Episodes originally aired weekly from July 2024 through November 2025 and remain just as relevant today.
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Listener reviews
Taken straight from Apple Podcasts, here what listeners have to say:
Sure, it's about career flipping on the surface...and each episode takes a deep dive in the "why" of the flips, the moments along the journey that take your breath away or slap you upside the head...filled with charm and energy and resonance. Listen in!
Carol Pearson
I highly recommend it...whether you're considering a career pivot, been through one yourself, or just want to hear about the twists and turns of some fascinating career journeys you'll come away learning something and likely leave each episode feeling inspired and less alone.
Hapmezzo
★★★★★
★★★★★
What you'll hear
No hustle, no hype — just real conversations about career change and becoming.
Honest Career Change Stories
Real experiences of people who flipped their careers — by choice, by necessity, or somewhere in between.
Identity Crisis & Vulnerability
Conversations about fear, burnout, doubt, and reinvention when your old title no longer fits.
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No "Right Timeline" Required
The Career Flipper was born during a time when I felt untitled, unwanted, and unsure where I belonged. I didn’t start it because I had answers, I started it because I was searching. These conversations held me together while I figured things out, and I hope they do the same for you.
- Jenny Dempsey, host & furniture flipper
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PLEASE NOTE: The Career Flipper podcast has evolved into a newsletter — a quieter place where I reflect on career change, creative pivots, second chances, and the in-between moments we don’t talk about enough.
If these conversations resonate, you’ll feel right at home.
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