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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 guests who have become unexpected mentors. She also opens up about juggling her full-time job, flipping furniture, grieving, and laughing her way through life, including the story of how she accidentally printed her misspelled logo on every piece of marketing material before her first big event.
This episode is honest, funny, and full of gratitude, a love letter to everyone who’s ever listened, shared, or dared to flip their own story.
What You’ll Hear:
THANK YOU FOR LISTENING, SUBSCRIBING, FOLLOWING, REVIEWING! I love and appreciate you all!
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 dog-walking app that completely changed his life. What started as a side gig turned into a thriving small business, and a huge boost to his wellbeing.
Jenny and Justin talk about what it takes to walk away from a “good on paper” career, the freedom of self-employment, the mental health perks of spending your days outside, and how dogs have a magical way of leading us exactly where we’re meant to go.
What you’ll hear:
Connect with Justin:
🐶 Instagram: @JustinWalksDogs
🌐 Website: justinwalksdogs.com
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 business, Human Insights Consulting Group, Jen’s story is proof that reinvention can happen at any stage, and that you’re never starting from scratch.
We dive into:
Whether you’re stuck in a role that doesn’t fit anymore or dreaming about your “someday” plan, Jen’s story will remind you that someday can start with just one small step.
Connect with Jenn
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 supporting women and sparking honest conversations about topics we don’t talk about enough, like menopause, mental health, and identity shifts.
And let me tell you: this conversation could not have come at a better time for me personally. I’m in the early days of my own perimenopause journey, and honestly, no one really prepares you for it. Lauren’s compassion, insight, and humor made me feel seen, and I think you’ll feel that too.
We get real about:
✨ Walking away from careers that no longer fit
✨ The identity shift that comes with major life transitions
✨ How perimenopause impacts your work, energy, and relationships
✨ The importance of saying no (without overexplaining)
✨ Mental health, motherhood, and permission to pivot, at any age
If you’ve ever found yourself wondering “Is it me, or is everything changing?”, this one’s for you.
Connect with Lauren
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 the chaos of baby product shopping. Because let’s be honest, the last thing overwhelmed parents need is another late-night Google spiral about strollers.
In this episode, Jane gets real about:
This is a conversation about courage, resilience, and choosing yourself, and your family, even when the path ahead is messy and unclear.
🎧 Listen now and connect with Jane below.
Connect with Jane
Episode Sponsor:
This episode is sponsored by Dwellspring. It’s an app I’ve been using that helps with sleep, focus, and just finding a little calm in the chaos. Think soundscapes, white noise, even custom mixes, all offline and totally ad-free.
If you want to try it, just search Dwellspring, like wellspring with a D, in the App Store or Google Play. And if you use the code Flipper, you’ll get a free month of Premium.
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 life that felt true to her.
In this episode, Manana shares:
Whether you’re just starting to wonder if there’s something more, or you’re already on the edge of making a leap — this conversation will give you permission to trust that voice inside you.
Connect with Manana
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 mapped out the stages of grief that come with job loss. Reading his book brought up so many of my own memories, everything from the shock and shame to that messy process of rebuilding your identity. It made me cry, it gave me hope, and it reminded me I’m not alone.
In this conversation with Steve, we talk about:
This one hit so close to home for me, and if you’ve ever been laid off, or even just wondered who you are without your job, I think it’ll resonate with you too.
Connect with Steve
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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, Hilary runs Pack Love and co-founded Wisdom of the Pack, a structured day camp for reactive dogs. In this conversation, she opens up about:
✨ How a bridge job as a paralegal gave her the space to heal
✨ The transferable skills she carried from her corporate career into entrepreneurship
✨ Why our detours, setbacks, and “nonlinear” paths are actually our training ground
✨ The deep lessons dogs can teach us about trust, presence, and joy
Whether you’re a dog lover, a career changer, or someone figuring out your “messy middle,” Hilary’s story will give you hope that second chances are always possible, even if they come with a few paw prints along the way.
Connect with Hilary
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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 founder of Rising Tide Consulting, she helps women leaders and entrepreneurs break through what she calls the inner glass ceiling: those voices of self-doubt, perfectionism, and “I’m not enough” that keep so many of us stuck.
We go deep into:
✨ What it’s really like to re-enter the workforce after years away raising kids
✨ How workplace bullying and politics shaped (and challenged) her career path
✨ Why women negotiate better for others than they do for themselves and how to flip that script
✨ The surprising way your strengths and values can be an anchor when you’re thinking about a career change
✨ Practical steps if you’re sitting at your desk right now, dreading another day in a job that doesn’t fit
This conversation is raw, vulnerable, and packed with insights for anyone who’s ever second-guessed themselves at work or wondered if it’s too late to start over.
Raina reminds us: the “hard stuff” you’ve gone through isn’t wasted. It can become the most powerful part of your story and the fuel for whatever you build next.
Connect with Raina:
🔗 Rising Tide Consulting
🔗 LinkedIn: Raina B. Gandhi
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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, curiosity, and passion for travel.
What You’ll Hear in This Episode:
Connect with Untethered Voyages
Thanks for tuning in to The Career Flipper!
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.
Let’s stay connected:
📲 Instagram: @thecareerflipperpod for all things podcast
💼 LinkedIn: The Career Flipper Podcast
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
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