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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

00:36:18

From social worker to financial coach, meet Annie Cole

The Career Flipper Podcast ·

2025/03/06

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, practical advice for anyone considering a career change or starting a business—like utilizing free resources,

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00:41:58

From corporate R&D to startup growth guiding...

The Career Flipper Podcast ·

2025/02/27

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 looking to grow personally and professionally.Here are some key takeaways from the episode:Yannick's love

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00:09:15

Cocoon Conversations: My career flip progress for...

The Career Flipper Podcast ·

2025/02/25

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 struggle with imposter syndrome. Jenny emphasizes the need for self-compassion during times of change and

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00:44:24

From UX designer to furniture maker, meet Ryan Kelly

The Career Flipper Podcast ·

2025/02/20

In this episode, host Jenny Dempsey chats with Ryan Kelly of Englewood, Colorado who flipped from a decade-long career in tech to creating human-centered furniture. He’s using his background in UX design to craft pieces that really connect with people. Ryan gets into the challenges he faces on a regular basis as he’s trying to figure it all out—everything from time management to outsourcing different parts of the job to how he will expand his operations one day. Plus, he shares how a solid support

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00:38:26

From nurse to professional organizer, meet Angelique...

The Career Flipper Podcast ·

2025/02/13

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 that aligns with her passion. She shares how her support system—family, friends, and a dash of

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00:37:37

From engineering to personal branding & marketing...

The Career Flipper Podcast ·

2025/02/06

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 background gave him a unique edge in his new career.His big dreams of building an audience and launching a

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00:44:18

From wedding planner and photographer to S’mores Cart...

The Career Flipper Podcast ·

2025/01/30

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 that idea into a successful business wasn’t all marshmallows and chocolate. Elyse and Kelley share the

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00:10:00

Cocoon Conversations: My Career Flip Progress for...

The Career Flipper Podcast ·

2025/01/28

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 the impact of her father’s advice and the challenges of starting over. She opens up about her new job

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00:34:10

From car sales and after school teacher to furniture...

The Career Flipper Podcast ·

2025/01/23

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 from teaching and sales to full-time furniture flipping.Her experience on the competition show The

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00:29:58

From corporate marketing & advertising to Caribbean...

The Career Flipper Podcast ·

2025/01/16

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 back home and living in his parents’ basement. But then, a “temporary” job in St. John, U.S. Virgin

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00:04:00

Get Ready for Season 2 of The Career Flipper!

The Career Flipper Podcast ·

2025/01/09

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 your own transition smoother.In this season, we’ll explore topics like:How to figure out what’s next when

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00:25:08

2024 Podcast recap: what I’ve learned so far from...

The Career Flipper Podcast ·

2024/12/17

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 the significance of overcoming fear and self-doubt while balancing practical needs with the pursuit of

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00:47:15

From sales account executive to certified...

The Career Flipper Podcast ·

2024/12/12

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 women in leadership through workshops, 1:1 coaching, and speaking events—work she now does full

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00:28:45

From high school English teacher to owner of E-WRITE,...

The Career Flipper Podcast ·

2024/12/10

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 a high school English teacher to becoming the owner of E-WRITE Online, a training consultancy where she

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00:36:05

From perinatal genetics counselor to SaaS customer...

The Career Flipper Podcast ·

2024/12/05

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 “one foot in, one foot out” approach to taking calculated risks, the importance of finding small moments

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00:34:27

From corporate communications specialist to career...

The Career Flipper Podcast ·

2024/12/03

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, and consulting. She’s taken all the lessons learned from those ups and downs, along with her

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00:10:51

A short story + personal message from Jenny Dempsey

The Career Flipper Podcast ·

2024/11/26

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 life often takes unexpected turns, and it’s all about embracing those changes and staying open to new

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00:46:11

From corporate marketing to pet waste management...

The Career Flipper Podcast ·

2024/11/21

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 after over a decade to start her own dog waste removal service, SD Scoop Squad, in sunny San Diego,

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00:29:27

From Ethics ThD to tech program manager, meet Julie...

The Career Flipper Podcast ·

2024/11/19

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 led her to question her long-term plans. Julie talks about the importance of staying open to change,

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00:35:01

From nursing to woodworking, meet Jake Conneen

The Career Flipper Podcast ·

2024/11/14

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 now running his own woodworking biz, Doby’s Craft House, named after his dog. Jake’s all about taking

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