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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

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All Episodes

00:24:59

2025 Podcast Recap: Gratitude, Growth & a Misspelled...

The Career Flipper Podcast ·

2025/11/06

In this heartfelt season wrap-up, host Jenny Dempsey reflects on everything The Career Flipper has become, and everyone who made it possible. What started as a personal experiment after being laid off has turned into a global community of second-chancers, dreamers, and brave souls rewriting their stories one imperfect step at a time.Jenny shares highlights from 2025: from a bartender in the Caribbean to a software engineer turned chocolate maker, and the lessons she’s learned from 86 incredible

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01:05:07

From the film industry to professional dog walker,...

The Career Flipper Podcast ·

2025/10/30

Sometimes your next career move comes with four paws and a leash. 🐾In this episode, Jenny chats with Justin Cohen, founder of Justin Walks Dogs in Los Angeles, about how he flipped his career, and his mental health, by trading spreadsheets and studio lots for sunshine, fresh air, and wagging tails.After years in the film industry, Justin was burnt out, anxious, and craving meaning. A wild trip abroad (involving a rat and a rabies scare, yes, really) led him back to LA, where he stumbled onto a

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00:35:26

From IT executive to founder & owner of Human...

The Career Flipper Podcast ·

2025/10/23

After two decades in government, most recently as Deputy Chief Information Officer for the New York State Office of Information Technology Services, Jenn Lorenz did something bold: she walked away.In this episode of The Career Flipper Podcast, host Jenny Dempsey chats with Jen about what it really takes to leave stability behind and create a career (and life) on your own terms. From her early days as a single mom rebuilding after divorce to building teams in IT leadership and now launching her own

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00:33:24

From lawyer to therapist and author, meet Lauren...

The Career Flipper Podcast ·

2025/10/16

In this week’s episode of The Career Flipper, I’m joined by Lauren Tetenbaum, a former lawyer turned psychotherapist and author, who’s made it her mission to help women navigate the big, messy transitions of life, from career pivots to motherhood to (yep) perimenopause.Lauren’s story is one of courage, self-awareness, and trusting your gut when the path you’re on just doesn’t fit anymore. After years in the legal world, she decided to build a life that aligned with her values, one centered around

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00:41:47

From product manager at Amazon to startup founder,...

The Career Flipper Podcast ·

2025/10/09

What happens when you spend 10 years at Amazon, love your job, love your team and then parenthood shakes everything up?That’s the story of Jane Dashevsky. Becoming a mom of two under two made her start asking the big questions: What do I really want for myself? For my family? That entrepreneurial spark she’d carried deep down finally pushed her to walk away from stability and build something of her own.Jane is now the founder of The Starter Set, an AI-powered service that helps parents cut through

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00:49:54

From psychology PhD to frontend software engineer and...

The Career Flipper Podcast ·

2025/10/02

What happens when you’ve done all the right things but still feel stuck, unfulfilled, or secretly unhappy in your career?That’s the story of today’s guest, Manana Jaworska, a career transition coach who knows firsthand how messy and complicated career change can be.From psychology student to PhD researcher, to programmer in Barcelona with the golden handcuffs, Manana has lived through multiple career flips. On paper, everything looked perfect. But inside, she was craving meaning, freedom, and a

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00:41:48

Laid off? Now what? Finding healing, hope and your...

The Career Flipper Podcast ·

2025/09/25

When host Jenny Dempsey got laid off back in 2022, she had no clue what I was doing. She was crying on her couch, trying to figure out who she even was without my job. No one hands you a guide for that kind of loss. It honestly felt like the ground fell out from under her.And then along comes Steve Jaffe. Turns out, he literally wrote the book I wish I had back then: The Layoff Journey: From Dismissal to Discovery.Steve’s been through four layoffs (yes, four!) and instead of letting it crush him, he

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00:40:50

From paralegal to dog psychologist and trainer, meet...

The Career Flipper Podcast ·

2025/09/18

Today I’m introducing you to Hilary, founder of Pack Love in San Diego.Hilary’s story is one of resilience, curiosity, and following the unexpected signs. After years working in operations and project management, while also navigating undiagnosed endometriosis that left her burnt out, she found herself searching for a new path. What started as a desperate attempt to help her own reactive dog led her into the world of dog psychology, community pack walks, and eventually building her own business.Now,

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00:37:29

From corporate banking to mother + leadership coach,...

The Career Flipper Podcast ·

2025/09/11

What happens when you step out of the workforce for 11 years to raise your kids and then try to step back in? For Raina Gandhi, it meant climbing back into high-pressure roles, bumping up against workplace politics (and yes, bullying), and eventually realizing she wanted something different.In this episode, Raina shares the very real story of her career flip from investment banking to higher ed leadership to being laid off, and how all of those experiences shaped the work she does today. Now, as the

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00:42:19

CX Leader & PreK Teacher + Cruise Event Cofounders,...

The Career Flipper Podcast ·

2025/09/04

In this episode of The Career Flipper, host Jenny Dempsey sits down with sisters Wendy and Elizabeth Pochop of Baltimore, Maryland, co-founders of Untethered Voyages, a side hustle turned passion project that creates cruise-based retreats for leaders, communities, and organizations.We connected through Support Driven, a global community for customer support professionals, and what started as a conversation about side hustles turned into an inspiring look at building something new from burnout,

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00:57:31

From talent acquisition to to Tai Chi instructor,...

The Career Flipper Podcast ·

2025/08/28

Meet Baiba Wisse, a multi-passionate creative from Raleigh, North Carolina, who spent a decade in global talent acquisition before life handed her a plot twist: a layoff. While she was still working in recruiting, Baiba discovered her favorite part of the job wasn’t the spreadsheets or the scheduling, it was the human connection. She loved coaching candidates, hearing their career stories, and helping people see their own potential.That passion inspired her to start her own podcast, The Career in

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00:35:02

From people operations manager to certified executive...

The Career Flipper Podcast ·

2025/08/21

From big tech at Meta to laid-off, new mom, and starting a coaching business from scratch, executive career coach Natalie Robbins of San Diego, CA knows what it means to reinvent. We talk about building a career that actually fits your life, starting over with a tiny human in tow, and why asking better questions can unlock your next chapter. If you’re feeling the pull toward something new, this episode is your reminder that you’re not behind, you’re just getting started.Connect with NatalieLinkedIn:

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00:57:56

From corporate banking to career transition coach &...

The Career Flipper Podcast ·

2025/08/14

What happens when life rips up your plan and hands you an unexpected invitation to start over?In this episode of The Career Flipper, host Jenny Dempsey sits down with Lori Wallace, executive recruiter, mentor, and all‑around career‑flipping muse. We talk about the serendipitous way we met (spoiler: Jenny was pretending I worked at an art show) and her journey from corporate banking to a total physical and emotional breakdown that changed everything.These days, we often hear stories about COVID being

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00:53:41

From donut maker to consumer & CX insights...

The Career Flipper Podcast ·

2025/08/07

In this episode, host Jenny Dempsey sits down with Beth Karawan, consumer & CX insights strategist, to talk about how a side hustle, a layoff, and a whole lot of curiosity led to an incredible career transformation. From student teaching and bartending to making donuts during the pandemic and launching her own consultancy, Beth’s journey is a reminder that your skills are transferable, your path is never linear, and joy can absolutely come from the most unexpected places.Topics We CoverWhen your

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00:41:43

A corporate sales and thrifted fashion curator, meet...

The Career Flipper Podcast ·

2025/07/31

This week, I got to chat with my friend Liz Dekofsky. She lives in LA, works full-time in a customer-facing job, and runs the coolest little side business curating thrifted style bundles.If you’ve ever walked into a thrift store and felt totally overwhelmed or just didn’t have the energy to dig through the racks, Liz gets it. That’s why she does the hunting for you, and her eye for finding great pieces is seriously next-level.But this episode goes deeper than just clothes.Liz recently got sober, and

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00:19:17

One year of flipping: Cocoon reflections, career...

The Career Flipper Podcast ·

2025/07/29

Welcome to a special solo episode of The Career Flipper Podcast! It’s the podcastaversary!One year ago, I hit publish on the very first episode of this show, having no idea what I was doing and definitely not realizing how much it would change my life. What started in the messy aftermath of a 2022 layoff (and 400+ job rejections) became a permission slip to rebuild, to reimagine success, and to start over without a map.In this episode, I share the behind-the-scenes of how this podcast came to be,

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00:43:26

Musicologist to strategic communications advisor,...

The Career Flipper Podcast ·

2025/07/24

What happens when you walk away from academia and turn your deep love of language, story, and the arts into a strategic superpower?In this episode of The Career Flipper Podcast, I sit down with Lisa Chensvold, a classically-trained soprano and former musicologist based in Washington, DC, who made a bold leap from the world of academia to the world of strategic communications.Now the Principal of Chensvold Communications, Lisa helps mission-driven leaders and organizations tackle complex

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00:53:42

From software engineer to customer experience to AI...

The Career Flipper Podcast ·

2025/07/17

In this episode, you’ll meet Mariena Quintanilla, a Los Angeles-based career flipper who proves you can pivot, even within the same industry.After spending nearly two decades in tech, moving through roles in software engineering, product management, solutions architecture, and customer experience (plus navigating a layoff), Mariena had a realization: she didn’t want to keep climbing the corporate ladder but she still loved tech.So, she made the leap. Today, Mariena runs Mellonhead.co, an AI

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00:34:04

Bathroom tile sales to personal brand & marketing...

The Career Flipper Podcast ·

2025/07/10

In this episode, host Jenny Dempsey chats with Joseph Rudd, who went from selling bathroom fixtures in London to managing personal brands in the marketing world. His journey is a real-deal look at what it takes to flip your career when everything feels uncertain.After the pandemic threw his career plans off course, Joseph didn’t wait for someone to give him a shot, he created his own opportunities. He started building experience from scratch, leaned into the world of personal branding, and learned

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00:41:35

From US Navy Captain to Professional Photographer,...

The Career Flipper Podcast ·

2025/07/03

What starts as a hobby can totally change your life—and Laura Hatcher is living proof.In this episode of The Career Flipper, I chat with Laura, a former Navy captain turned full-time professional photographer based in Alexandria, Virginia. Her journey from military structure to creative entrepreneurship is honest, emotional, and so deeply inspiring.We talk about:Transitioning from military to civilian lifeFinding identity outside the uniformImposter syndrome and self-doubt as a creativeBuilding a

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