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PODCAST

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

business careers

All Episodes

00:39:11

From head of marketing to visual artist, meet Galina...

The Career Flipper Podcast ·

2024/11/12

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 podcast host of In the Art Scene Podcast but also the founder of the San Diego Art Directory, a nonprofit that

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00:34:28

From CPA/CFO/finance leader to executive and...

The Career Flipper Podcast ·

2024/11/07

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 staying true to your values is key when making those big decisions. Plus, he highlights the power of

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00:32:11

From Corporate COO to General Contractor & Interior...

The Career Flipper Podcast ·

2024/10/31

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 relationships became key to her success. Kendra also gets real about the fear and self-doubt that comes with leaving

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00:32:06

From corporate head of sales & marketing to startup...

The Career Flipper Podcast ·

2024/10/29

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 his career once—he’s done it twice. First, he left his stable enterprise job to join a startup in a

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00:29:57

From baker & pastry chef to global CX leader, meet...

The Career Flipper Podcast ·

2024/10/24

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 curiosity has shaped his journey and reminds us that careers don’t need to follow a straight line—you can find

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00:40:02

From behind the corporate desk to out in the field as...

The Career Flipper Podcast ·

2024/10/22

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. They dive into the importance of setting clear goals, overcoming obstacles, and having a strong support

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00:42:19

From geographer to public speaker & trainer, meet...

The Career Flipper Podcast ·

2024/10/17

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 speaking workshops, communication coaching, and geospatial consulting.Frank dives into the power of

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00:34:36

From VP of Sales in manufacturing to workplace trauma...

The Career Flipper Podcast ·

2024/10/10

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 business, which sparked his love for problem-solving and team development. Over the years, he’s made several

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00:34:21

From nutritionist to software developer, meet...

The Career Flipper Podcast ·

2024/10/08

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 wasn’t her calling. After several career flips—from moving abroad and teaching English to working in

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00:31:05

From real estate & law enforcement to founding Cucina...

The Career Flipper Podcast ·

2024/10/03

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 their pizza recipes and using Instagram to build a loyal following, one delicious slice at a time.But the

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00:38:50

From music teacher to baker, meet Cat Cheng

The Career Flipper Podcast ·

2024/10/01

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, including how COVID-19 impacted her journey and the struggles she faced with narcolepsy. Cat also shares

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00:26:51

SaaS sales director to divorce therapist, meet Jason...

The Career Flipper Podcast ·

2024/09/26

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 navigating similar challenges. He talks about how important it is to seek help during hard times and

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00:35:10

Customer service agent to licensed electrician, meet...

The Career Flipper Podcast ·

2024/09/24

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 about staying true to your values, facing fears of failure, and finding real fulfillment by following

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00:30:22

From marketing director to owner of Sun Divers,...

The Career Flipper Podcast ·

2024/09/19

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 risks, setting boundaries, and pursuing passion led her to a fulfilling new life that blends diving with

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00:29:56

SAT tutor to the creator of Murdle, meet G.T. Karber

The Career Flipper Podcast ·

2024/09/12

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 rebranding, connecting with a specific audience, and the importance of feedback from those who resonate with

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00:31:46

SEO specialist to surf-inspired artist, meet Ethan...

The Career Flipper Podcast ·

2024/09/05

Have you ever been stuck in traffic on your long commute home, wondering if there's more to life than this?In this episode, Ethan Orenstein takes us through his incredible journey from journalism to content writing, SEO, and digital marketing. Along the way, he discovered his passion for surfboard design and art, which led him to create Wave Arcade, a business selling bamboo surfboard fins. Despite setbacks like the COVID-19 pandemic and algorithm changes, Ethan adapted by refocusing on his art,

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00:28:03

Museum curator to teacher, meet Kimberly Masiello

The Career Flipper Podcast ·

2024/08/29

Imagine going to school for your dream career, only to have a friend's dinner conversation open your eyes to a new path you never considered. Suddenly, you want to shift your whole journey!In this episode, meet Kimberly Masiello, a career flipper who’s transitioned from studying art history and curating museum exhibits to teaching, becoming a principal, and now virtually teaching ESL with her own small business.In this episode, you’ll hear how Kimberly emphasizes the power of listening and

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00:34:55

Comedian to keynote speaker on digital balance, meet...

The Career Flipper Podcast ·

2024/08/22

Ever wondered what it takes to leap from one career to another, chasing dreams and overcoming doubts along the way? Meet Jeff Wozer! Jeff's career flip story starts with a dream of being a hockey play-by-play announcer, pivots into stand-up comedy, and then transitions into a fulfilling career as a speaker. In this episode, Jeff opens up about the challenges he faced and the doubts that tried to hold him back, all while emphasizing the power of believing in yourself and following your true

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00:55:57

From MiLB pitcher to country hip hop recording...

The Career Flipper Podcast ·

2024/08/20

Ever wondered what it’s like to pursue your childhood dream of becoming an MiLB pitcher for the Houston Astros, only to find that it's just one chapter in a much grander story? In this episode, Zach Dando from Denver, Colorado, shares his incredible career journey, spanning from the excitement of professional baseball to coaching 350 games, turning pro in golf, ranching, and now creating music that’s garnered over 500k streams on Spotify. Zach opens up about the highs and lows of each transition,

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00:19:35

From hospitality manager to content manager/writer,...

The Career Flipper Podcast ·

2024/08/15

Ever wondered how far a career flip could take you? Tracy Carmen Watkin shares her journey from hospitality to managing office buildings to moving to Europe and becoming a writer and content manager. Join us as she discusses overcoming imposter syndrome and navigating job searches, all while pursuing her passion for personal training and planning a travel curation business.Tracy recounts her journey from managing office buildings to relocating to Europe and embracing writing. She opens up about

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87 results

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