The Career Flipper Podcast

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...

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...

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, f...

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 t...

Let’s just say Megan Pawlak did not take the straight path to becoming a powerhouse HR consultant. She started out in food service, rolled through the corporate world, and eventually said, “Yeah... I think I’ll start my own thing.” Now she runs Benandanti Consulting, helping early-stage startups grow without turning into soul-sucking corporate machines. She’s a pro at finding the right people, say...

In this episode of the Career Flipper podcast, Jenny Dempsey chats with Brian Feretic about his journey from being a neuroscientist to becoming a resin artist and entrepreneur. Brian opens up about how he dealt with layoffs, found his passion for plants, and even started a social marketplace for plant lovers. He talks about the ups and downs of switching careers, the importance of taking a step ba...

In this April 2025 "cocoon episode" of the Career Flipper podcast, host Jenny, gets real about her own story of jumping back into the corporate world after being laid off. She chats about how she juggles her day job with her creative side gigs and why giving yourself a second chance is so important. Jenny shares those little moments of joy she finds in her weekend projects and opens up about why s...

Tonya Cassidy has been a middle school teacher near Piedmont, North Carolina, for her whole career — and she loves her students. But on the side? She’s been running Appaloosa Artisans, her furniture restoration business, creating seriously gorgeous pieces for her clients. And now, with retirement on the horizon, Tonya’s getting ready to take her furniture business full-time — which is kind of wild...

In this episode of The Career Flipper podcast, host Jenny Dempsey sits down with Alex Ferro of Winston-Salem, North Carolina. He opens up about his career shift from corporate banking to real estate — and the personal journey that led him there. After his dad passed, Alex started questioning what success really meant to him. He realized that climbing the corporate ladder wasn’t cutting it anymore...

In this episode of the Career Flipper podcast, host Jenny Dempsey chats with Hannah Slack, from Sheffield, England. She is a freelance writer who made the leap from academia to marketing. Hannah, who holds a PhD in history, opens up about her journey of stepping away from academia because of mental health challenges and finding her groove in freelance writing. She talks about the early hurdles of...

Today on The Career Flipper , host Jenny Dempsey is chatting with Michael Mattson, whose career journey is a perfect example of how small, intentional shifts can lead to massive transformations. Michael started out as a mail carrier, delivering letters door to door—and yes, getting to pet all the dogs along the way! But beyond the friendly pups, he saw firsthand the importance of both customer and...

In this episode, host Jenny Dempsey is sitting down with Carol Pearson from Bay City, Michigan—founder of 10 Little Rules, an independent publishing house. Carol’s career journey has taken plenty of twists and turns. She started in corporate PR and marketing, moved into freelancing, and eventually built her own publishing business. But this conversation isn’t just about career changes—it’s about l...

In this episode of the Career Flipper podcast, our host Jenny Dempsey gets real about her journey back to full-time work after being laid off for two years. She opens up about the tough times she faced while applying for over 400 jobs and how each rejection hit hard, making her question her identity, which was so tied to her career. Jenny also talks about her adventures in flipping furniture and p...

In this episode of the Career Flipper podcast, Jenny Dempsey chats with Julie Hanell, who's originally from Switzerland, lived all over and has had quite the diverse career path. Julie's done it all—from modeling to running a coffee shop in South Africa, starting a tech company aimed at empowering women, and working in talent acquisition. Nowadays, she's the head of growth at a global company and...

Changing careers isn’t just about updating your resume—it’s a big, emotional transition that can shake up your sense of identity, self-worth, and even how you move through the world. In this episode, career flipper host Jenny Dempsey sits down with Licensed Professional Counselor, Katie Asmus, founder and director of the Somatic Nature Therapy Institute headquartered in Boulder, CO, to dive into t...

In this episode, host Jenny Dempsey chats with Annie Cole of Vancouver, WA, a financial coach who’s no stranger to career flipping. Annie shares her journey from social work to education, then ed tech, and finally launching her own business focused on financial coaching for women. Along the way, she’s learned the importance of self-care while making intentional career moves. She offers real, pract...

In this episode, host Jenny Dempsey chats with Yannick Willemin, a seasoned expert in the composites industry who’s been at it for 20 years, fueled by his passion for sports. Based in Zurich, Switzerland, Yannick shares how he’s navigated career transitions, embraced change, and built authentic connections along the way. His journey offers valuable lessons for anyone considering a career flip or l...

In this episode of the Career Flipper podcast, host Jenny Dempsey shares her personal journey of transitioning back to corporate life after a period of entrepreneurship and creative pursuits. She discusses the emotional challenges of adjusting to a structured work environment, the importance of finding balance between her corporate job and her passion for furniture flipping, and the ongoing strugg...

In this episode of the "Career Flipper" podcast, host Jenny Dempsey interviews Ryan Kelly, who transitioned from a decade-long career in tech to founding Humm Furniture. Ryan shares his journey of creating thoughtful, human-centered furniture and discusses the challenges of this career shift, including time management and overcoming analysis paralysis. He emphasizes the importance of taking action...

In this episode, host Jenny Dempsey chats with Angelique Beach in San Diego, California , who took the leap from nursing to become a professional organizer and founded her own business, Neatly —and what a transformation it’s been! Angelique unpacks her journey and gets real about the challenges she faced, from feeling unfulfilled in her nursing career to navigating the transition to a business tha...

In today’s episode, host Jenny Dempsey chats with Ghalib Hassam, who shares his inspiring story of going from pursuing a master’s in engineering in Pakistan to starting his own business in marketing and personal branding in the UK. Ghalib opens up about: Navigating imposter syndrome and complex family dynamics. Why taking risks and putting yourself out there is always worth it. How his engineering...

In this episode, host Jenny Dempsey sits down with Elyse Rowen and Kelley Williams, two unstoppable entrepreneurs who both run their own individual companies of planning weddings and capturing moments behind the camera to creating a luxury dessert experience with The S'mores Cart in San Luis Obispo, California. It all started with a lightbulb moment during a road trip to Disneyland. But turning th...

In this heartfelt Bonus Cocoon episode of The Career Flipper podcast, Jenny Dempsey takes you behind the scenes of her personal career-flipping journey. From 18 years in customer service to unexpected layoffs, she shares how resilience, rejection, and a dash of creativity led her to furniture flipping, podcasting, and rediscovering her purpose. Jenny reflects on lessons from her past, including th...

In this episode of The Career Flipper podcast, host Jenny Dempsey chats with Mariah Howard of Murrieta, California, a former teacher and sales professional who took the leap to become a full-time furniture flipper. Mariah shares her inspiring journey of leaving a traditional job to follow her passion for furniture restoration. Here’s what you’ll hear about in this episode: How Mariah transitioned...

Welcome to the first episode of Season 2 of The Career Flipper Podcast !  Host Jenny Dempsey kicks things off with career flipper Matthew Smith. Matthew went from working in corporate advertising in New York City to bartending in the Caribbean. Yep, you read that right! After losing his job right before COVID, struggling to find a new one, and going through a tough breakup, Matthew ended up moving...