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 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:The evolution from Season 1 (post-layoff chaos) to Season 2 (balancing full-time work + creative passion)Key takeaways from this year’s most inspiring guestsThe hilarious Canva logo fiasco at Jenny’s first vendor eventWhy messy beginnings still count as beginningsA peek at what’s next for The Career Flipper in Spring 2026 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 hello@thecareerflipper.com 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.comSeason 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:Leaving a stable film career for a happier lifeHow walking dogs improved Justin’s mental health and daily routineTurning a side hustle into a full-time businessThe realities of building your own path (and income)Finding meaning, flexibility, and peace — one walk at a timeConnect 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 hello@thecareerflipper.com 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.comSeason 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:What it’s like to leave a stable, 20-year government career by choiceThe emotional side of change, managing fear, imposter syndrome, and “what ifs”How to repurpose your skills into something completely newCreating a business that supports the life you want now (not 30 years from now)Why your future self deserves the good life tooThe story behind her upcoming book, 10 Little Rules for Getting It DoneWhether 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 JennGet her book, 10 Little Rules for Getting IT Done: https://10littlerules.com/store/10-Little-Rules-for-Getting-IT-Done-p779037877LinkedIn: linkedin.com/in/jennlorenzHuman Insights Consulting: insightbyhumans.com/services-main 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 hello@thecareerflipper.com 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.comSeason 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 ageIf you’ve ever found yourself wondering “Is it me, or is everything changing?”, this one’s for you.Connect with LaurenBuy the book: https://thecounselaur.com/millennialmenopausebook/ Her website: https://thecounselaur.com/Instagram: https://www.instagram.com/thecounselaur/LinkedIn: https://www.linkedin.com/in/laurenatetenbaum/ 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 hello@thecareerflipper.com 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.comSeason 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:Leaving a steady job after a decade at AmazonThe identity shift that comes with walking away from stabilityParenting while building a startup (the real messy middle)Testing ideas piece by piece and finding her way in Seattle’s startup worldHow to not let numbers or social media dictate your worthThis 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 JaneLinkedInThe Starter SetThe Starter Set InstagramListen to Getting Started with BabyEpisode 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 hello@thecareerflipper.com 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.comSeason 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:How cultural and family expectations shaped her early career choicesWhy it’s so important to get real about the day-to-day reality of a job (before you jump into it)The moment she realized stability wasn’t enough — and what gave her the courage to walk awayHow she now helps clients find clarity, define their values, and create careers that align with who they areWhether 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 MananaInstagram: @careerchangeguide LinkedIn: Manana Jaworska 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 hello@thecareerflipper.com 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.comSeason 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:Why losing a job takes you through the grieving process.The awkward shame we carry after a layoff, and how to drop it.Why slowing down to process before jumping into the job hunt can change everythingThe “baggage” you might unknowingly carry into your next role.And what you need to hear if you just got laid off yesterday.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 SteveGrab Steve’s book The Layoff Journey on Amazon: The Layoff JourneyLearn more at: thestevejaffe.comFollow Steve on Instagram: @stevejaffethelayoffjourneyConnect with Steve on LinkedIn: Steve Jaffe on LinkedIn 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 hello@thecareerflipper.com 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.comSeason 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 joyWhether 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 HilaryInstagram: @packlovesdWebsite: packloveca.comWisdom of the Pack Day Camp: wisdomofthepack.comInstagram (Wisdom of the Pack): @wisdomofthepack 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 hello@thecareerflipper.com 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.comSeason 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 fitThis 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 hello@thecareerflipper.com 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.comSeason 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:How Wendy’s burnout in customer success led to a sabbatical, curiosity, and eventually a pivot toward travel and hospitality.The family cruise that sparked the idea for Untethered Voyages and how it evolved from “workations at sea” into curated community-building retreats.The unique way Wendy and Elizabeth balance their strengths, vision and execution, while building a business together as sisters, roommates, and travel buddies.Why structure, accountability, and small sacrifices are key to making side hustles work alongside full-time jobs.Practical advice for anyone feeling stuck in their career: start small, find joy outside of work, and solve a problem you’ve already faced for others.Their big vision: living and working full-time from cruise ships while helping groups create unforgettable experiences. Connect with Untethered VoyagesJoin their Alaska adventure next summer www.untetheredvoyages.com/alaska.BONUS: They will waive the planning fee for Career Flipper Podcast listeners, if you go on the trip, use code "Career Flipper"!Connect on Instagram: https://www.instagram.com/untetheredvoyagesvacations/Connect on LinkedIn: https://www.linkedin.com/company/untethered-voyagesBook your own group retreat at sea: untetheredvoyages.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 hello@thecareerflipper.com 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.comSeason 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? 💫

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 Technicolor, where she interviews people about their career journeys in living color. But when the layoff hit, she found herself in that all-too-familiar “what now?” moment.Instead of sitting still (because that’s not her style), Baiba leaned into her creative energy, painting, cooking, cleaning, and trying new things. She also followed her curiosity into movement and stress relief, recently earning her Tai Chi instructor certification. Now, she’s on a mission to bring Tai Chi into corporate settings, helping teams manage stress, move more, and age well.I met Baiba early in my own podcasting journey, and we’ve been swapping ideas and cheering each other on ever since. She’s been a generous supporter, a creative sounding board, and now I’m flipping the mic so you can hear her story.What You’ll Learn in This Episode:How Baiba turned a layoff into an opportunity to explore new passions Why coaching and human connection were the most rewarding parts of her recruiting career The creative outlets that kept her moving forward during a career pivot How Tai Chi can help reduce stress and support well-being in and out of the workplace The joy (and challenges) of podcasting about other people’s career journeysConnect with BaibaConnect with Baiba on LinkedIn: https://www.linkedin.com/in/bwisse/ Listen to The Career in TechnicolorApple: https://podcasts.apple.com/us/podcast/career-in-technicolor/id1584835608Spotify: https://open.spotify.com/show/034sss7E8ncD5RewpqkwZJ Follow on Instagram: https://www.instagram.com/careerintechnicolor/  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 hello@thecareerflipper.com 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.comSeason 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? 💫

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: https://www.linkedin.com/in/natalie-robbins-25561789/Career Coaching: https://www.pivotinpower.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 hello@thecareerflipper.com 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.comSeason 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 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 the turning point for career change but Lori takes us back to another moment that shook the world: 9/11. It was the catalyst that impacted her health, her career, and ultimately, the way she lives and works today.In this conversation, Lori shares:How the events of 9/11 sent shockwaves through her health and careerWhat it’s like to be laid off while on maternity leaveThe moment her body forced her to pause and completely reevaluate her lifeWhy listening to your body’s signals during transition is non‑negotiableHow career change can be one of the most misunderstood (and isolating) forms of modern traumaIf you’ve ever felt like the rug’s been pulled out from under you, stuck, scared, or unsure of what’s next, this one’s going to meet you right where you are.Connect with Lori:🌿 The Great Compassion🌿 Career Ecology🌿 LinkedIn 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 hello@thecareerflipper.com 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.comSeason 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, 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 major doesn’t match your futureMarket research, storytelling, and discovering you’re good at math, kind ofWhat a restaurant job taught Beth about trust and leadershipLetting go of shame around unconventional jobsLaunching “It’s Donut Friday” and leaning into funThe surprising link between CX and making donuts Connect with BethLinkedIn: https://www.linkedin.com/in/bethcaranNewsletter: It’s Donut Friday  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 hello@thecareerflipper.com 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.comSeason 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? 💫

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 it’s been a huge turning point in her life. That decision gave her the clarity and confidence to stop hiding parts of herself and start doing more of what lights her up. We talk about what it’s like to balance a side hustle with a full-time job, how she deals with imposter syndrome (hint: it’s still there, but she doesn’t let it run the show), and how she’s learning to show up more fully as herself.If you’ve been sitting on an idea, waiting for the perfect moment, or thinking you need to be “fully ready” before you start something, this episode is your permission slip to just go for it.Starting messy is still starting. And Liz is proof that small steps can lead to big, beautiful changes.Let’s get into it.Connect with Liz & buy a bundleInstagram: https://www.instagram.com/curatedbylizd 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 hello@thecareerflipper.com 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.comSeason 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? 💫

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, how flipping furniture helped me flip my identity, and how conversations with guests like:Nick Musica, a former SEO guy turned animal psychicTrish Jasinski, who bought a chateau in the south of France and left corporate to open a retreat spaceCat Cheng, a former music teacher turned Netflix-featured baker (hi, tres leches dreams)And Case Sandberg, who I met at a farmer’s market and learned had just left his software engineering job to become a chocolate maker…helped me feel less alone and more alive.Oh and I’m sharing a piece of my music. I wrote a song called Just Wait, about getting laid off, getting lost, and learning how to come back to yourself.Skip to 14:28 if you want to jump straight to the song.Whether you’re in the middle of your own career flip, cocoon season, or identity unraveling, I hope this episode reminds you that you don’t need permission from anyone else to change your life.You can give it to yourself.🎧 Listen, share, and leave a review if this one resonates. 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 hello@thecareerflipper.com 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.comSeason 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 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 communication challenges—from defining a CEO’s voice to aligning internal teams and rethinking how strategy shows up in language. Her work is rooted in clarity, intentionality, and the belief that thoughtful communication is leadership.We talk about:Why she pivoted away from academia How she turned her humanities background into a strength in a STEM-obsessed worldWhat it’s like to build a consulting business from scratchHow communications can help shape and reshape organizations at every levelThe fear (and thrill) of taking the leap into entrepreneurshipIf you’re someone who’s ever felt the nudge to pivot but wondered how your experience translates, this one’s for you.Connect with LisaLinkedIn: https://www.linkedin.com/in/lisachensvold/Chensvold Communications: https://chensvoldcommunications.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 hello@thecareerflipper.com 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.comSeason 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, 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 education and consulting company helping others make sense of emerging technology.In our conversation, we talk about:The inner work that happens before, during, and after a big leapBuilding a financial safety net and jumping anywayThe identity shifts that come with walking away from a titleWhy knowing who you are matters more than knowing where you’re goingMariena doesn’t sugarcoat the messy middle. She shares what it really felt like to start over, the fears she faced, and the courage it took to rebuild on her own terms.Connect with MarienaLinkedIn: https://www.linkedin.com/in/mariena/Website: https://mellonhead.co/ 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 hello@thecareerflipper.com 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.comSeason 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, 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 how to stand out by being, well...himself.We talk about:Making big career changes without a traditional backgroundWhy networking isn’t as scary as it soundsThe magic of having supportive people in your cornerWhat to do when self-doubt shows upHow to start building a personal brand—even if you’re not in marketingWhy your portfolio matters more than your degree Joseph’s story is a reminder that it’s never too late to start something new, and you don’t need a fancy title or perfect plan to begin. You just have to start.✨ If you’ve ever thought, “Who’s going to take me seriously?”, this one’s for you.Connect with JosephLinkedIn: https://www.linkedin.com/in/josephrudd/Instagram: https://www.instagram.com/worklifewithjoe/?hl=en 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 hello@thecareerflipper.com 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.comSeason 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 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 business from a side passionHow mentorship and community helped her growThe emotional side of setting “big” goalsNavigating cultural identity and belonging in new spacesAdapting through the pandemic and learning as she wentIf you're in the thick of a transition—or wondering if your side project has legs—Laura's story will meet you where you are, and maybe even give you that little nudge to keep going.🎧 Listen wherever you get your podcasts and don’t forget to subscribe, rate, and leave a review if this one resonates!Connect with Laura Hatcher:📸 Website📷 Instagram📘 Facebook🎥 YouTube💼 LinkedIn 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 hello@thecareerflipper.com 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.comSeason 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? 💫