Hosted by Jenny Dempsey · 🇺🇸 US · EN · 87 episodes
Established thought leaders with verified media credentials.
Thinking about making a career change but have no idea where to start? You’re not alone.Welcome to The Career Flipper, the podcast for anyone wondering, "What else is out there?". I’m Jenny Dempsey—your host and a fellow career flipper. I didn’t plan on changing careers, but after years in customer experience and a surprise layoff, I found myself asking, "How do people actually make big career moves? And more importantly, how do they keep going when it gets messy, overwhelming, and scary?"That curiosity led me to just ask people who have done it. To have real, honest conversations with people from all over the world who’ve made all kinds of career flips. Whether they started over in a new industry, turned a side hustle into a full-time gig, or made a total 180 to do something they actually love, their stories gave me ideas, inspiration, and even a little courage - so I figured they might give that to you too.Be sure to subscribe on your favorite podcast platform for new episodes ev
Jenny Dempsey hosts The Career Flipper Podcast, a business show with 87 episodes published.
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 off has turned into a g
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 his mental health, by
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 this episode of The
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 transitions of life, from c
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 start asking the big qu
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 who knows firsthand
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 that kind of loss. It h
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 project management, while
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 workplace politics (and
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 project that creates cru
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 in recruiting, Baiba
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 building a career that act
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 recruiter, mentor, and all‑a
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 career transformation. From
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 ever walked into a thr
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 definitely not realizing
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 Chensvold, a classic
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 roles in software en
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 what it takes to flip y
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 photographer based in A
Jenny Dempsey
San Diego Furniture Flipper · Diamond Rail Services
1 appearance on this show
Justin Cohen
founder and managing partner · Justin Walks Dogs
1 appearance on this show
Lauren Tetenbaum
women’s health advocate, licensed therapist (and attorney) · LCSW
1 appearance on this show
Steve Jaffe
author of "The Layoff Journey: From Dismissal to Discovery" · New York County District Attorney's Office
1 appearance on this show
Baiba Wisse
Tai Chi Qigong Coach
1 appearance on this show
Lori Wallace
1 appearance on this show
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The Career Flipper Podcast is hosted by Jenny Dempsey. The show is categorised under business (careers) and has published 87 episodes.
The Career Flipper Podcast has published 87 episodes.
The Career Flipper Podcast regularly covers business, careers, entrepreneurship. It sits in the business category, with a careers focus.
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Episodes of The Career Flipper Podcast average 43 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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