The Career Flipper Podcast

Welcome to Season 2 of The Career Flipper ! In this episode, host Jenny Dempsey kicks off the new season with a sneak peek into what’s coming your way. Expect more real stories from people around the world who’ve made career changes, from all industries and backgrounds. Jenny dives into the ups and downs of career flips, including personal struggles, wins, and advice you can actually use to make y...

In this episode, host Jenny Dempsey reflects on the journey of her podcast, 'The Career Flipper,' sharing insights gained from interviewing various guests who have successfully navigated career changes. She discusses the importance of finding one's calling, transferring skills from past experiences, taking calculated risks, and the necessity of continuous learning and adaptation. Jenny emphasizes...

What if you have a successful six-figure career but still don’t feel fulfilled? That’s exactly what Marina Movsissian from Paris, France, experienced. In this episode,  Marina shares her journey from a thriving marketing and sales career, including time with Google in Dublin and San Francisco, to starting her own coaching business, EmpowerMov. While juggling her full-time job, Marina began helping...

Have you ever been asked by your boss to take on something totally outside your job description, and then suddenly, you’re discovering a whole new skill or side of yourself? It’s funny how these little pivots can change everything about how we see our potential. Meet Leslie O’Flahavan! She’s someone who didn’t make a huge leap, but instead slid her career forward, moving from nine amazing years as...

How do you navigate a career pivot as a new parent, especially when you realize your old job, that you still love, just doesn’t fit your life anymore? In this episode, you’ll meet Lauren Rose Eimers from Boise, Idaho, who’s been on a winding career journey, moving from mental health to genetic counseling and ultimately to customer experience leadership in the tech startup world. We dive into her “...

Have you ever had a really good job, maybe even your dream job, take a turn for the worse?  I’m so excited to welcome Kathleen “Kate” Goggin! Kate’s a pro at navigating career changes, and she’s here to share her journey and some hard-earned insights on making career shifts work for you. Kate’s background is wide-ranging—she’s worked in radio and TV production, web writing, outreach, media affairs...

Have you ever had a project that just didn’t go as planned? In this episode, Jenny Dempsey shares a personal story about a furniture project that didn’t quite work out the way she hoped—but ended up creating a great opportunity for someone else. She dives into the lessons she learned from this setback and highlights the importance of community and support during tough times.  Jenny reminds us that...

Have you ever walked down the street and spotted a pile of dog doo just sitting there? Even with doo-doo bags available from the city or apartment complex, some folks just don’t bother to pick it up. It's gross, right? And let's be real—nobody wants that mess ending up on their shoes! Now, let me introduce you to Courtney Copeland. She made a big career change, leaving her corporate marketing job...

What happens when the career you’ve spent decades working toward doesn’t turn out the way you expected?  In this episode, Julie Morris from Seattle, Washington shares her career flip story of shifting from academia, where she received her doctorate in ethics and worked as a professor, to a whole new path in tech as a program manager. She opens up about facing a toxic work environment and how it le...

How do you know when it's time to make a big career change, even if you're not sure what’s next? In this episode, I’m excited to reconnect with Jake Conneen, who I know from high school in the little Southern California town we grew up in, Norco. Now based in El Paso, Texas, Jake shares his wild ride of career flips—from construction to journalism, restaurant management, the military, nursing, and...

Have you ever stopped to really listen to what your body and mind are telling you about your work? In this episode, Galina Marcus shares her career flip story, and it’s full of valuable lessons. She started in the fashion industry in Russia, then moved into marketing in the tech world, but eventually, she made the choice to follow her passion for art. Now, she's not only a visual artist and podcas...

Ok, quick question for you: Ever feel like your work and identity are all tangled up? Today, we’re chatting with Ricky Padgett from Burlington, Vermont. He’s a certified executive and leadership coach, and he’s been there. In this episode, Ricky shares his career flip story—from being a CFO to still doing CPA work, while coaching others to navigate their own big career changes. He talks about how...

What would you do if you weren’t afraid of failing? In this episode, we hear from Kendra Roy, an incredible interior designer and general contractor in San Diego, California, about her journey from working a stable job to starting her own business. She opens up about the real challenges she faced—especially in gaining respect as a woman in the construction world—and how building strong relationshi...

Ever wondered what it’s like to step away from the comfort of a steady corporate job and dive headfirst into the whirlwind of founding your own startup, where you’re suddenly the one wearing all the hats?  Meet Tushar Jain from India. He is the founder of Enthu.ai , a software designed to help coach sales and customer service agents, improving overall customer experiences. Tushar didn’t just flip...

What can baking bread and pastries teach you about working in the customer experience tech space? In today’s episode, host Jenny Dempsey introduces you to Luke Jamieson from Melbourne, Australia. He started out as a baker and pastry chef, wrangled some cattle, tried his hand at graphic design, and eventually discovered his true passion in the customer experience (CX) world. Luke shares how curiosi...

Are you a sports fan curious about how to make the leap from a corporate desk to the field, reporting on the games you love? In this episode of The Career Flipper podcast, host Jenny Dempsey chats with Chris Hayre, a CBS LA Sports anchor and reporter and creator of the Los Angeles Chargers weekly podcast about his transition from corporate marketing with the Los Angeles Lakers to sports media. The...

Feeling stuck in your career, or are you keeping an open mind? In this episode, Frank Winters from Schenectady, NY, shares his incredible career flip. After 35 years as New York State's Geographic Information Officer (GIO) and holding leadership roles like Executive Director of the Geospatial Advisory Council, Frank decided to pivot. Now, as the owner of WintersGeo Inc., he's all about public spea...

What can we learn from micro-pivots, those little hop, skips and cookie crumbs we take and leave on the path as we navigate our career? In this episode, we meet Rob Connelly from Charleston, South Carolina, who went from VP of Sales in the manufacturing industry to starting his own business as a workplace trauma coach. Rob’s journey started with helping turn around his cousin’s window and door bus...

Have you ever felt like your career path just wasn’t the right fit, even after putting in years of effort?  In this episode, you’ll meet Danielle Lewis, a Texas native who’s been living in Barcelona, Spain for 12 years. Career flipping is practically in her DNA, and she shares her journey of making bold choices to shape her own path. Danielle started out as a nutritionist, but soon realized it was...

What challenges could come up when you turn your passion into a business?  In this episode, your host Jenny Dempsey chats with Ashley and Tony Ross, the dynamic duo behind Cucina de Pizza in San Diego, California. They share their incredible journey of leaving behind their careers in real estate and law enforcement to dive headfirst into the pizza business. Ashley and Tony started by perfecting th...

What does it take to leave a job you love, even when you know it’s no longer the right fit for your health? In today’s episode, we chat with Cat Cheng from New York—who you might know from Netflix’s "Blue Ribbon Baking Championship". Cat made the bold switch from being a music teacher to becoming a successful home baker and content creator. She opens up about the challenges of her career change, i...

What if you took something really tough you went through and turned it into a way to help others going through the same thing? That’s exactly what Jason did. He went from dreaming of a baseball career to working as director of sales in the SaaS world, and then made a huge shift to becoming a men's divorce therapist. After facing his own difficult divorce, Jason realized he wanted to support others...

Ever wondered what it’s like to go from customer service to becoming a licensed electrician in Spain? Join me as I chat with Jeff Watkin about his inspiring journey from California to Barcelona, where he traded in screen time for hands-on work. We dive into the challenges he faced, his motivation for making the leap, and how he worked through imposter syndrome and childhood trauma. We’ll also talk...

Ever wondered what it’s like to swap a high-pressure corporate job for running a dive shop on a remote island?  Natalie Shuman’s journey takes us from the hustle world of marketing to the clear blue waters of Roatan. She opens up about the pressures, recognition, and burnout from her previous career, and how she and her husband followed their dream to own a dive shop. Discover how taking smart ris...

Ever wondered how to take your scattered creative ideas and turn them into a focused, intentional career? G.T. Karber has cracked the code! From juggling various creative projects to becoming a successful mystery writer and creator of the Murdle, an award winning mystery puzzle book series, G.T. shares his journey of honing in on a niche. He talks about the power of intentional branding and rebran...