The Career Flipper Podcast

Jenny Dempsey
  • 5.0 (10)
  • CAREERS
  • UPDATED WEEKLY

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 every Thursday. Got your own flip story? I’d love to hear it! Submit your story for a future episode at https://www.thecareerflipper.com Follow on Instagram: @thecareerflipperpod You don’t have to have it all figured out. Just take that first step. What's the best that could happen?

  1. 2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

    11/06/2025

    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 off has turned into a global community of second-chancers, dreamers, and brave souls rewriting their stories one imperfect step at a time. 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 laughing her way through life, including the story of how she accidentally printed her misspelled logo on every piece of marketing material before her first big event. This episode is honest, funny, and full of gratitude, a love letter to everyone who’s ever listened, shared, or dared to flip their own story. What You’ll Hear: The evolution from Season 1 (post-layoff chaos) to Season 2 (balancing full-time work + creative passion)Key takeaways from this year’s most inspiring guestsThe hilarious Canva logo fiasco at Jenny’s first vendor eventWhy messy beginnings still count as beginningsA peek at what’s next for The Career Flipper in Spring 2026  THANK YOU FOR LISTENING, SUBSCRIBING, FOLLOWING, REVIEWING! I love and appreciate you all! Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    25 min
  2. From the film industry to professional dog walker, meet Justin Cohen

    10/30/2025

    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 his mental health, by trading spreadsheets and studio lots for sunshine, fresh air, and wagging tails. 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. What started as a side gig turned into a thriving small business, and a huge boost to his wellbeing. Jenny and Justin talk about what it takes to walk away from a “good on paper” career, the freedom of self-employment, the mental health perks of spending your days outside, and how dogs have a magical way of leading us exactly where we’re meant to go. What you’ll hear: Leaving a stable film career for a happier lifeHow walking dogs improved Justin’s mental health and daily routineTurning a side hustle into a full-time businessThe realities of building your own path (and income)Finding meaning, flexibility, and peace — one walk at a timeConnect with Justin: 🐶 Instagram: @JustinWalksDogs 🌐 Website: justinwalksdogs.com   Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    1h 5m
  3. From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz

    10/23/2025

    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 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 can happen at any stage, and that you’re never starting from scratch. We dive into: What it’s like to leave a stable, 20-year government career by choiceThe emotional side of change, managing fear, imposter syndrome, and “what ifs”How to repurpose your skills into something completely newCreating a business that supports the life you want now (not 30 years from now)Why your future self deserves the good life tooThe story behind her upcoming book, 10 Little Rules for Getting It DoneWhether you’re stuck in a role that doesn’t fit anymore or dreaming about your “someday” plan, Jen’s story will remind you that someday can start with just one small step. Connect with Jenn Get her book, 10 Little Rules for Getting IT Done: https://10littlerules.com/store/10-Little-Rules-for-Getting-IT-Done-p779037877LinkedIn: linkedin.com/in/jennlorenzHuman Insights Consulting: insightbyhumans.com/services-main Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    35 min
  4. From lawyer to therapist and author, meet Lauren Tetenbaum

    10/16/2025

    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 transitions of life, from career pivots to motherhood to (yep) perimenopause. 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 talk about enough, like menopause, mental health, and identity shifts. And let me tell you: this conversation could not have come at a better time for me personally. I’m in the early days of my own perimenopause journey, and honestly, no one really prepares you for it. Lauren’s compassion, insight, and humor made me feel seen, and I think you’ll feel that too. We get real about: ✨ Walking away from careers that no longer fit ✨ The identity shift that comes with major life transitions ✨ How perimenopause impacts your work, energy, and relationships ✨ The importance of saying no (without overexplaining) ✨ Mental health, motherhood, and permission to pivot, at any age If you’ve ever found yourself wondering “Is it me, or is everything changing?”, this one’s for you. Connect with Lauren Buy the book: https://thecounselaur.com/millennialmenopausebook/ Her website: https://thecounselaur.com/Instagram: https://www.instagram.com/thecounselaur/LinkedIn: https://www.linkedin.com/in/laurenatetenbaum/ Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    33 min
  5. From product manager at Amazon to startup founder, meet Jane Dashevsky

    10/09/2025

    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 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. Jane is now the founder of The Starter Set, an AI-powered service that helps parents cut through the chaos of baby product shopping. Because let’s be honest, the last thing overwhelmed parents need is another late-night Google spiral about strollers. In this episode, Jane gets real about: Leaving a steady job after a decade at AmazonThe identity shift that comes with walking away from stabilityParenting while building a startup (the real messy middle)Testing ideas piece by piece and finding her way in Seattle’s startup worldHow to not let numbers or social media dictate your worthThis is a conversation about courage, resilience, and choosing yourself, and your family, even when the path ahead is messy and unclear. 🎧 Listen now and connect with Jane below. Connect with Jane LinkedInThe Starter SetThe Starter Set InstagramListen to Getting Started with BabyEpisode Sponsor: This episode is sponsored by Dwellspring. It’s an app I’ve been using that helps with sleep, focus, and just finding a little calm in the chaos. Think soundscapes, white noise, even custom mixes, all offline and totally ad-free. If you want to try it, just search Dwellspring, like wellspring with a D, in the App Store or Google Play. And if you use the code Flipper, you’ll get a free month of Premium. Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    42 min
  6. From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska

    10/02/2025

    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 who knows firsthand how messy and complicated career change can be. From psychology student to PhD researcher, to programmer in Barcelona with the golden handcuffs, Manana has lived through multiple career flips. On paper, everything looked perfect. But inside, she was craving meaning, freedom, and a life that felt true to her. In this episode, Manana shares: How cultural and family expectations shaped her early career choicesWhy it’s so important to get real about the day-to-day reality of a job (before you jump into it)The moment she realized stability wasn’t enough — and what gave her the courage to walk awayHow she now helps clients find clarity, define their values, and create careers that align with who they areWhether you’re just starting to wonder if there’s something more, or you’re already on the edge of making a leap — this conversation will give you permission to trust that voice inside you. Connect with Manana Instagram: @careerchangeguide LinkedIn: Manana Jaworska Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    50 min
  7. Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey

    09/25/2025

    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 that kind of loss. It honestly felt like the ground fell out from under her. And then along comes Steve Jaffe. Turns out, he literally wrote the book I wish I had back then: The Layoff Journey: From Dismissal to Discovery. Steve’s been through four layoffs (yes, four!) and instead of letting it crush him, he mapped out the stages of grief that come with job loss. Reading his book brought up so many of my own memories, everything from the shock and shame to that messy process of rebuilding your identity. It made me cry, it gave me hope, and it reminded me I’m not alone. In this conversation with Steve, we talk about: Why losing a job takes you through the grieving process.The awkward shame we carry after a layoff, and how to drop it.Why slowing down to process before jumping into the job hunt can change everythingThe “baggage” you might unknowingly carry into your next role.And what you need to hear if you just got laid off yesterday.This one hit so close to home for me, and if you’ve ever been laid off, or even just wondered who you are without your job, I think it’ll resonate with you too. Connect with Steve Grab Steve’s book The Layoff Journey on Amazon: The Layoff JourneyLearn more at: thestevejaffe.comFollow Steve on Instagram: @stevejaffethelayoffjourneyConnect with Steve on LinkedIn: Steve Jaffe on LinkedIn Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    42 min
  8. From paralegal to dog psychologist and trainer, meet Hilary Pratt

    09/18/2025

    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 project management, while also navigating undiagnosed endometriosis that left her burnt out, she found herself searching for a new path. What started as a desperate attempt to help her own reactive dog led her into the world of dog psychology, community pack walks, and eventually building her own business. Now, Hilary runs Pack Love and co-founded Wisdom of the Pack, a structured day camp for reactive dogs. In this conversation, she opens up about: ✨ How a bridge job as a paralegal gave her the space to heal ✨ The transferable skills she carried from her corporate career into entrepreneurship ✨ Why our detours, setbacks, and “nonlinear” paths are actually our training ground ✨ The deep lessons dogs can teach us about trust, presence, and joy Whether you’re a dog lover, a career changer, or someone figuring out your “messy middle,” Hilary’s story will give you hope that second chances are always possible, even if they come with a few paw prints along the way. Connect with Hilary Instagram: @packlovesdWebsite: packloveca.comWisdom of the Pack Day Camp: wisdomofthepack.comInstagram (Wisdom of the Pack): @wisdomofthepack Thanks for tuning in to The Career Flipper! If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor: 💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet.   Let’s stay connected:   📲 Instagram: @thecareerflipperpod for all things podcast 💼 LinkedIn: The Career Flipper Podcast 🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper   Submit your story: Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.   Want to support the show or work together?   Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com   Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.   🎵 Music Credits   Season 1: Intro & outro music by Audionautix.com Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio   And hey, remember my favorite question: What’s the best that could happen? 💫

    41 min
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About

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 every Thursday. Got your own flip story? I’d love to hear it! Submit your story for a future episode at https://www.thecareerflipper.com Follow on Instagram: @thecareerflipperpod You don’t have to have it all figured out. Just take that first step. What's the best that could happen?

Information

  • Creator
    Jenny Dempsey
  • Years Active
    2024 - 2025
  • Episodes
    87
  • Rating
    Clean
  • Copyright
    © 2024 - The Career Flipper Podcast
  • Show Website
    The Career Flipper Podcast