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 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?
Episodes
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‑around career‑flipping muse. We talk about the serendipitous way we met (spoiler: Jenny was pretending I worked at an art show) and her journey from corporate banking to a total physical and emotional breakdown that c...
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 student teaching and bartending to making donuts during the pandemic and launching her own consultancy, Beth’s journey is a reminder that your skills are transferable, your path is never linear, and joy can absolut...
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 thrift store and felt totally overwhelmed or just didn’t have the energy to dig through the racks, Liz gets it. That’s why she does the hunting for you, and her eye for finding great pieces is seriously next-level.
But t...
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 how much it would change my life. What started in the messy aftermath of a 2022 layoff (and 400+ job rejections) became a permission slip to rebuild, to reimagine success, and to start over without a map.
In this epis...
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 classically-trained soprano and former musicologist based in Washington, DC, who made a bold leap from the world of academia to the world of strategic communications.
Now the Principal of Chensvold Communications, Lisa helps...
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 engineering, product management, solutions architecture, and customer experience (plus navigating a layoff), Mariena had a realization: she didn’t want to keep climbing the corporate ladder but she still loved tech.
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 your career when everything feels uncertain.
After the pandemic threw his career plans off course, Joseph didn’t wait for someone to give him a shot, he created his own opportunities. He started building experience fr...
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 Alexandria, Virginia. Her journey from military structure to creative entrepreneurship is honest, emotional, and so deeply inspiring.
We talk about:
- Transitioning from military to civilian life
- Finding identity outsi...
Sometimes a joke turns into a new life.
Trish Jasinski had built a fulfilling, decades-long career in corporate marketing—and she really loved it. But during the pandemic, while working remotely from a very tiny Paris apartment, she started joking with friends that châteaux in the countryside were cheaper than her shoebox of a flat.
Just for fun—and with zero plans to actually buy—she went château shopping.
And then it happened. She s...
In this episode of "Cocoon Conversations," host Jenny Dempsey gets real about the emotional rollercoaster of juggling her career and furniture-flipping side hustle. She spills on burnout, imposter syndrome, and the chaos of pricing her art (“Am I worth it?!”). Jenny shares her messy, vulnerable moments—singing to her furniture, doubting herself, and still showing up. She reminds us that spirals aren’t failures, but part of the proc...
What happens when a software engineer follows a sweet little spark of curiosity all the way to the farmer’s market? In this episode, host Jenny Dempsey chats with Case Sandberg, founder of San Diego Chocolate Co., about what it really looks like to leave a stable tech job and step into the (often melty) world of handcrafted chocolate.
We talk about perfectionism, pivoting with purpose, building something from scratch, and why your n...
Today’s guest is Carolene Méli, a ghostwriter for live entertainment executives and whose career has been anything but predictable. She started out studying nutrition, but what followed was a 20-year adventure in the live entertainment world. Carolene spent 11 of those years as the Guest Experience Manager of VIP Experiences at Cirque du Soleil, traveling to 17 countries, managing six different shows, and creat... Mark as Played June 5, 2025 • 36 mins This week, Jenny chats with Katie O’Malley, founder of Encourage Coaching, whose career path took her from the world of politics and nonprofits to coaching individuals from underrepresented communities into leadership roles. Katie’s story is one of heart, grit, and staying deeply connected to her “why.” Together, they dive into the emotional side of career pivots, what it takes to build a business that actually cares, and how listen... Mark as Played May 29, 2025 • 43 mins In this episode of The Career Flipper, I chat with Jenna Leveille, who went from working as a merchant in the travelling Renaissance Festival circuit to becoming the Deputy State Cartographer of Arizona and now she’s the VP of State and Local Government Strategy at a mapping company. But this journey? It’s anything but straight. Jenna’s path weaves through non-traditional college years, a detour into zoology (because saving the wor... Mark as Played May 27, 2025 • 15 mins In this episode of "Cocoon Conversations" on the Career Flipper podcast, I, Jenny Dempsey, take you along on my career journey. This year, I’ve committed to opening up about my own career flip, just as I encourage my guests to do. So here we are, in May 2025, and I can hardly believe it’s been four months since I started my current day job. It feels surreal to say that, especially considering I was laid off for two years before th... Mark as Played May 22, 2025 • 44 mins In today’s episode, we’re talking with Alexia, a holistic canine nutritionist who made an unexpected career flip, thanks to her dog. Alexia started her journey deep in the world of academia and art in the sustainability sector, researching, writing, and painting. But then her dog (yes, her sweet pup, Lucky) flipped her whole life upside down in the best way possible. Now? She helps dogs thrive, feel better, eat better, and live lon... Mark as Played May 15, 2025 • 40 mins In this episode of The Career Flipper Podcast, host Jenny Dempsey chats with Victoria Tara, a Ukrainian-born contemporary artist based in Miami with a story that’s full of heart, bold choices, and beautiful color (literally and figuratively). Victoria shares her journey of flipping from a career in psychology and real estate and interior design to becoming a full-time artist. She opens up about the inspiration behind her vibrant pai... Mark as Played May 8, 2025 • 53 mins
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