The Career Flipper Podcast

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

The Career Flipper Podcast is a business podcast hosted by Jenny Dempsey, with 87 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jenny Dempsey hosts The Career Flipper Podcast, a business show with 87 episodes published.

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  Episode #78

  2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

  Nov 6, 202525 minS0

  <p>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 global community of second-chancers, dreamers, and brave souls rewriting their stories one imperfect step at a time.</p><p>Jenny shares highlights from 2025: from a bartender in the Caribbean to a software engineer turned chocolate maker, and the lessons she’s learned from 86 incredible guests who have become unexpected mentors. She also opens up about juggling her full-time job, flipping furniture, grieving, and la...

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  Episode #77

  From the film industry to professional dog walker, meet Justin Cohen

  Oct 30, 20251h 5mS0

  <p>Sometimes your next career move comes with four paws and a leash. 🐾</p><p>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 trading spreadsheets and studio lots for sunshine, fresh air, and wagging tails.</p><p>After years in the film industry, Justin was burnt out, anxious, and craving meaning. A wild trip abroad (involving a rat and a rabies scare, yes, really) led him back to LA, where he stumbled onto a dog-walking app that completely changed his life. Wha...

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  Episode #76

  From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz

  Oct 23, 202535 minS0

  <p>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.</p><p>In this episode of The Career Flipper Podcast, host Jenny Dempsey chats with Jen about what it really takes to leave stability behind and create a career (and life) on your own terms. From her early days as a single mom rebuilding after divorce to building teams in IT leadership and now launching her own business, Human Insights Consulting Group, Jen’s story is proof that reinvention ca...

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  Episode #75

  From lawyer to therapist and author, meet Lauren Tetenbaum

  Oct 16, 202533 minS0

  <p>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 career pivots to motherhood to (yep) perimenopause.</p><p>Lauren’s story is one of courage, self-awareness, and trusting your gut when the path you’re on just doesn’t fit anymore. After years in the legal world, she decided to build a life that aligned with her values, one centered around supporting women and sparking honest conversations about topics we don’t tal...

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  Episode #74

  From product manager at Amazon to startup founder, meet Jane Dashevsky

  Oct 9, 202542 minS0

  <p>What happens when you spend 10 years at Amazon, love your job, love your team and then parenthood shakes everything up?</p><p>That’s the story of Jane Dashevsky. Becoming a mom of two under two made her start asking the big questions: What do I really want for myself? For my family? That entrepreneurial spark she’d carried deep down finally pushed her to walk away from stability and build something of her own.</p><p>Jane is now the founder of The Starter Set, an AI-powered service that helps parents cut through the chaos of baby product shop...

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