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The Career Flipper Podcast
Jenny Dempsey
86 episodes
4 days ago
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?
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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?
Show more...
Careers
Business,
Society & Culture,
Entrepreneurship,
Documentary
Episodes (20/86)
The Career Flipper Podcast
From the film industry to professional dog walker, meet Justin Cohen
From the film industry to professional dog walker, meet Justin Cohen of Justin Walks Dogs in Los Angeles, CA.
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4 days ago
1 hour 5 minutes 7 seconds

The Career Flipper Podcast
From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz
From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz in Albany, New York.
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1 week ago
35 minutes 26 seconds

The Career Flipper Podcast
From lawyer to therapist and author, meet Lauren Tetenbaum
From lawyer to therapist and author, meet Lauren Tetenbaum of New York, NY.
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2 weeks ago
33 minutes 24 seconds

The Career Flipper Podcast
From product manager at Amazon to startup founder, meet Jane Dashevsky
From product manager at Amazon to Founder of The Starter Set, meet Jane Dashevsky of Seattle, WA
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3 weeks ago
41 minutes 47 seconds

The Career Flipper Podcast
From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska
From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska in Colombia
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1 month ago
49 minutes 54 seconds

The Career Flipper Podcast
Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey
Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey
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1 month ago
41 minutes 48 seconds

The Career Flipper Podcast
From paralegal to dog psychologist and trainer, meet Hilary Pratt
From paralegal to dog psychologist and trainer, meet Hilary Pratt of San Diego, California
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1 month ago
40 minutes 50 seconds

The Career Flipper Podcast
From corporate banking to mother + leadership coach, meet Raina Gandhi
From corporate banking to mother + leadership coach, meet Raina Gandhi in Baltimore, Maryland
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1 month ago
37 minutes 29 seconds

The Career Flipper Podcast
CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop
CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop of Baltimore, Maryland
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2 months ago
42 minutes 19 seconds

The Career Flipper Podcast
From talent acquisition to to Tai Chi instructor, meet Baiba Wisse
From talent acquisition director to Tai Chi instructor, meet Baiba Wisse of Raleigh, North Carolina
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2 months ago
57 minutes 31 seconds

The Career Flipper Podcast
From people operations manager to certified executive coach, meet Natalie Robbins
From people operations manager to certified executive coach, meet Natalie Robbins in San Diego, California
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2 months ago
35 minutes 2 seconds

The Career Flipper Podcast
From corporate banking to career transition coach & recruiter, meet Lori Wallace
From corporate banking to founder of Career Ecology and The Great Compassion, career transition coach & recruiter, meet Lori Wallace of Carlsbad, CA
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2 months ago
57 minutes 56 seconds

The Career Flipper Podcast
From donut maker to consumer & CX insights strategist, meet Beth Karawan
From donut maker to consumer & CX insights strategist, meet Beth Karawan in New York, NY.
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2 months ago
53 minutes 41 seconds

The Career Flipper Podcast
A corporate sales and thrifted fashion curator, meet Liz Dekofsky
A corporate sales and thrifted fashion curator, meet Liz Dekofsky in Los Angeles, California
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3 months ago
41 minutes 43 seconds

The Career Flipper Podcast
One year of flipping: Cocoon reflections, career chaos & an original song
One year of flipping: Cocoon reflections, career chaos & an original song
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3 months ago
19 minutes 17 seconds

The Career Flipper Podcast
Musicologist to strategic communications advisor, meet Lisa Chensvold
Musicologist to strategic communications advisor, meet Lisa Chensvold of Washington, DC.
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3 months ago
43 minutes 26 seconds

The Career Flipper Podcast
From software engineer to customer experience to AI entrepreneur, meet Mariena Quintanilla
From software engineer to customer experience to AI entrepreneur, meet Mariena Quintanilla in Los Angeles, CA.
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3 months ago
53 minutes 42 seconds

The Career Flipper Podcast
Bathroom tile sales to personal brand & marketing manager, meet Joseph Rudd
Bathroom tile sales to personal brand & marketing manager, meet Joseph Rudd in London, England.
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3 months ago
34 minutes 4 seconds

The Career Flipper Podcast
From US Navy Captain to Professional Photographer, meet Laura Hatcher
From US Navy Captain to Professional Photographer, meet Laura Hatcher in Alexandria, Virginia
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4 months ago
41 minutes 35 seconds

The Career Flipper Podcast
From corporate marketing to chateau owner & event curator, meet Trish Jasinski
From corporate marketing to chateau owner & event curator, meet Trish Jasinski of Château de Gère, a 14th-century stone fortress tucked into the Vallée d’Ossau in southwest France.
Show more...
4 months ago
46 minutes 29 seconds

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?