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?
Site
RSS
Apple
Données mises à jour le 04/07/2026
Classements récents
Dernières positions dans les classements Apple Podcasts et Spotify.
Liens partagés entre épisodes et podcasts
Liens présents dans les descriptions d'épisodes et autres podcasts les utilisant également.
2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo
Épisode 78
jeudi 6 novembre 2025 • Durée 24:59
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 guests
The hilarious Canva logo fiasco at Jenny’s first vendor event
Why messy beginnings still count as beginnings
A 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.
🪑 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? 💫
From the film industry to professional dog walker, meet Justin Cohen
Épisode 77
jeudi 30 octobre 2025 • Durée 01:05:07
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 life
How walking dogs improved Justin’s mental health and daily routine
Turning a side hustle into a full-time business
The realities of building your own path (and income)
Finding meaning, flexibility, and peace — one walk at a time
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.
From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz
Épisode 76
jeudi 23 octobre 2025 • Durée 35:26
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 choice
The emotional side of change, managing fear, imposter syndrome, and “what ifs”
How to repurpose your skills into something completely new
Creating a business that supports the life you want now (not 30 years from now)
Why your future self deserves the good life too
The story behind her upcoming book, 10 Little Rules for Getting It Done
Whether 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.
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
From lawyer to therapist and author, meet Lauren Tetenbaum
Épisode 75
jeudi 16 octobre 2025 • Durée 33:24
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/
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.
From product manager at Amazon to startup founder, meet Jane Dashevsky
Épisode 74
jeudi 9 octobre 2025 • Durée 41:47
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 Amazon
The identity shift that comes with walking away from stability
Parenting while building a startup (the real messy middle)
Testing ideas piece by piece and finding her way in Seattle’s startup world
How to not let numbers or social media dictate your worth
This is a conversation about courage, resilience, and choosing yourself, and your family, even when the path ahead is messy and unclear.
Episode 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.
From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska
Épisode 73
jeudi 2 octobre 2025 • Durée 49:54
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 choices
Why 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 away
How she now helps clients find clarity, define their values, and create careers that align with who they are
Whether 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.
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.
Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey
Épisode 72
jeudi 25 septembre 2025 • Durée 41:48
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 everything
The “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.
From paralegal to dog psychologist and trainer, meet Hilary Pratt
Épisode 71
jeudi 18 septembre 2025 • Durée 40:50
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.
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.
From corporate banking to mother + leadership coach, meet Raina Gandhi
Épisode 70
jeudi 11 septembre 2025 • Durée 37:29
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 yes, bullying), and eventually realizing she wanted something different.
In this episode, Raina shares the very real story of her career flip from investment banking to higher ed leadership to being laid off, and how all of those experiences shaped the work she does today. Now, as the founder of Rising Tide Consulting, she helps women leaders and entrepreneurs break through what she calls the inner glass ceiling: those voices of self-doubt, perfectionism, and “I’m not enough” that keep so many of us stuck.
We go deep into:
✨ What it’s really like to re-enter the workforce after years away raising kids ✨ How workplace bullying and politics shaped (and challenged) her career path ✨ Why women negotiate better for others than they do for themselves and how to flip that script ✨ The surprising way your strengths and values can be an anchor when you’re thinking about a career change ✨ Practical steps if you’re sitting at your desk right now, dreading another day in a job that doesn’t fit
This conversation is raw, vulnerable, and packed with insights for anyone who’s ever second-guessed themselves at work or wondered if it’s too late to start over.
Raina reminds us: the “hard stuff” you’ve gone through isn’t wasted. It can become the most powerful part of your story and the fuel for whatever you build next.
CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop
Épisode 69
jeudi 4 septembre 2025 • Durée 42:19
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 cruise-based retreats for leaders, communities, and organizations.
We connected through Support Driven, a global community for customer support professionals, and what started as a conversation about side hustles turned into an inspiring look at building something new from burnout, curiosity, and passion for travel.
What You’ll Hear in This Episode:
How Wendy’s burnout in customer success led to a sabbatical, curiosity, and eventually a pivot toward travel and hospitality.
The family cruise that sparked the idea for Untethered Voyages and how it evolved from “workations at sea” into curated community-building retreats.
The unique way Wendy and Elizabeth balance their strengths, vision and execution, while building a business together as sisters, roommates, and travel buddies.
Why structure, accountability, and small sacrifices are key to making side hustles work alongside full-time jobs.
Practical advice for anyone feeling stuck in their career: start small, find joy outside of work, and solve a problem you’ve already faced for others.
Their big vision: living and working full-time from cruise ships while helping groups create unforgettable experiences.
Découvrez des podcasts liées à The Career Flipper Podcast. Explorez des podcasts avec des thèmes, sujets, et formats similaires. Ces similarités sont calculées grâce à des données tangibles, pas d'extrapolations !
🪑 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? 💫
💌 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.
🪑 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? 💫
🪑 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? 💫
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.
🪑 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? 💫
🪑 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? 💫
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.
🪑 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? 💫
🪑 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? 💫
!
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.
🪑 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? 💫
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.
🪑 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? 💫
