The Career Flipper Podcast

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 Carib...

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...

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 da...

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...

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...

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...

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 Dism...

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...

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 l...

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 co...

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 hel...

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 e...

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 ph...

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 i...

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...

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 s...

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 o...

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 corporat...

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 opportunitie...

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...

Sometimes a joke turns into a new life. Trish Jasinski had built a fulfilling, decades-long career in corporate marketing—and she really loved it. But during the pandemic, while working remotely from a very tiny Paris apartment, she started joking with friends that châteaux in the countryside were cheaper than her shoebox of a flat. Just for fun—and with zero plans to actually buy—she went château...

In this episode of "Cocoon Conversations," host Jenny Dempsey gets real about the emotional rollercoaster of juggling her career and furniture-flipping side hustle. She spills on burnout, imposter syndrome, and the chaos of pricing her art (“Am I worth it?!”). Jenny shares her messy, vulnerable moments—singing to her furniture, doubting herself, and still showing up. She reminds us that spirals ar...

What happens when a software engineer follows a sweet little spark of curiosity all the way to the farmer’s market? In this episode, host Jenny Dempsey chats with Case Sandberg, founder of San Diego Chocolate Co., about what it really looks like to leave a stable tech job and step into the (often melty) world of handcrafted chocolate. We talk about perfectionism, pivoting with purpose, building so...

Today’s guest is Carolene Méli, a ghostwriter for live entertainment executives and whose career has been anything but predictable. She started out studying nutrition, but what followed was a 20-year adventure in the live entertainment world. Carolene spent 11 of those years as the Guest Experience Manager of VIP Experiences at Cirque du Soleil, traveling to 17 countries, managing six different sh...

This week, Jenny chats with Katie O’Malley, founder of Encourage Coaching, whose career path took her from the world of politics and nonprofits to coaching individuals from underrepresented communities into leadership roles. Katie’s story is one of heart, grit, and staying deeply connected to her “why.” Together, they dive into the emotional side of career pivots, what it takes to build a business...