The Career Flipper Podcast
Jenny Dempsey
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2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo
In this heartfelt season wrap-up, host Jenny Dempsey reflects on everything The Career Flipper has become, and everyone who made it possible. What started as a personal experiment after being laid…
From the film industry to professional dog walker, meet Justin Cohen
Sometimes your next career move comes with four paws and a leash. 🐾In this episode, Jenny chats with Justin Cohen, founder of Justin Walks Dogs in Los Angeles, about how he flipped his career, and…
From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz
After two decades in government, most recently as Deputy Chief Information Officer for the New York State Office of Information Technology Services, Jenn Lorenz did something bold: she walked away.In…
From lawyer to therapist and author, meet Lauren Tetenbaum
In this week’s episode of The Career Flipper, I’m joined by Lauren Tetenbaum, a former lawyer turned psychotherapist and author, who’s made it her mission to help women navigate the big, messy…
From product manager at Amazon to startup founder, meet Jane Dashevsky
What happens when you spend 10 years at Amazon, love your job, love your team and then parenthood shakes everything up?That’s the story of Jane Dashevsky. Becoming a mom of two under two made her…
From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska
What happens when you’ve done all the right things but still feel stuck, unfulfilled, or secretly unhappy in your career?That’s the story of today’s guest, Manana Jaworska, a career transition coach…
Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey
When host Jenny Dempsey got laid off back in 2022, she had no clue what I was doing. She was crying on her couch, trying to figure out who she even was without my job. No one hands you a guide for…
From paralegal to dog psychologist and trainer, meet Hilary Pratt
Today I’m introducing you to Hilary, founder of Pack Love in San Diego.Hilary’s story is one of resilience, curiosity, and following the unexpected signs. After years working in operations and…
From corporate banking to mother + leadership coach, meet Raina Gandhi
What happens when you step out of the workforce for 11 years to raise your kids and then try to step back in? For Raina Gandhi, it meant climbing back into high-pressure roles, bumping up against…
CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop
In this episode of The Career Flipper, host Jenny Dempsey sits down with sisters Wendy and Elizabeth Pochop of Baltimore, Maryland, co-founders of Untethered Voyages, a side hustle turned passion…
From talent acquisition to to Tai Chi instructor, meet Baiba Wisse
Meet Baiba Wisse, a multi-passionate creative from Raleigh, North Carolina, who spent a decade in global talent acquisition before life handed her a plot twist: a layoff. While she was still working…
From people operations manager to certified executive coach, meet Natalie Robbins
From big tech at Meta to laid-off, new mom, and starting a coaching business from scratch, executive career coach Natalie Robbins of San Diego, CA knows what it means to reinvent. We talk about…
From corporate banking to career transition coach & recruiter, meet Lori Wallace
What happens when life rips up your plan and hands you an unexpected invitation to start over?In this episode of The Career Flipper, host Jenny Dempsey sits down with Lori Wallace, executive…
From donut maker to consumer & CX insights strategist, meet Beth Karawan
In this episode, host Jenny Dempsey sits down with Beth Karawan, consumer & CX insights strategist, to talk about how a side hustle, a layoff, and a whole lot of curiosity led to an incredible…
A corporate sales and thrifted fashion curator, meet Liz Dekofsky
This week, I got to chat with my friend Liz Dekofsky. She lives in LA, works full-time in a customer-facing job, and runs the coolest little side business curating thrifted style bundles.If you’ve…
One year of flipping: Cocoon reflections, career chaos & an original song
Welcome to a special solo episode of The Career Flipper Podcast! It’s the podcastaversary!One year ago, I hit publish on the very first episode of this show, having no idea what I was doing and…
Musicologist to strategic communications advisor, meet Lisa Chensvold
What happens when you walk away from academia and turn your deep love of language, story, and the arts into a strategic superpower?In this episode of The Career Flipper Podcast, I sit down with Lisa…
From software engineer to customer experience to AI entrepreneur, meet Mariena Quintanilla
In this episode, you’ll meet Mariena Quintanilla, a Los Angeles-based career flipper who proves you can pivot, even within the same industry.After spending nearly two decades in tech, moving through…
Bathroom tile sales to personal brand & marketing manager, meet Joseph Rudd
In this episode, host Jenny Dempsey chats with Joseph Rudd, who went from selling bathroom fixtures in London to managing personal brands in the marketing world. His journey is a real-deal look at…
From US Navy Captain to Professional Photographer, meet Laura Hatcher
What starts as a hobby can totally change your life—and Laura Hatcher is living proof.In this episode of The Career Flipper, I chat with Laura, a former Navy captain turned full-time professional…
Frequently Asked Questions
The Career Flipper Podcast has published 87 episodes since May 2024, covering topics in Business, Careers.
The Career Flipper Podcast is currently dormant with new episodes weekly. Average episode length is 36m.
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