The Career Flipper Podcast

2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 6 Nov 2025 08:00:00 +0000

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 guests
The hilarious Canva logo fiasco at Jenny’s first vendor event
Why messy beginnings still count as beginnings
A 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.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? 💫

From the film industry to professional dog walker, meet Justin Cohen

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 30 Oct 2025 07:00:00 +0000

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 life
How walking dogs improved Justin’s mental health and daily routine
Turning a side hustle into a full-time business
The realities of building your own path (and income)
Finding meaning, flexibility, and peace — one walk at a time

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:

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

🎵 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? 💫

From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 23 Oct 2025 07:00:00 +0000

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 choice
The emotional side of change, managing fear, imposter syndrome, and “what ifs”
How to repurpose your skills into something completely new
Creating a business that supports the life you want now (not 30 years from now)
Why your future self deserves the good life too
The story behind her upcoming book, 10 Little Rules for Getting It Done

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

Get her book, 10 Little Rules for Getting IT Done: https://10littlerules.com/store/10-Little-Rules-for-Getting-IT-Done-p779037877
LinkedIn: linkedin.com/in/jennlorenz
Human 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:

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

🎵 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? 💫

From lawyer to therapist and author, meet Lauren Tetenbaum

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 16 Oct 2025 07:00:00 +0000

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

Buy 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:

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

🎵 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? 💫

From product manager at Amazon to startup founder, meet Jane Dashevsky

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 9 Oct 2025 07:00:00 +0000

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 Amazon
The identity shift that comes with walking away from stability
Parenting while building a startup (the real messy middle)
Testing ideas piece by piece and finding her way in Seattle’s startup world
How to not let numbers or social media dictate your worth

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:

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

🎵 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? 💫

From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 2 Oct 2025 07:00:00 +0000

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 choices
Why 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 away
How she now helps clients find clarity, define their values, and create careers that align with who they are

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

Instagram: @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:

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

🎵 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? 💫

Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layoff Journey

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 25 Sep 2025 07:00:00 +0000

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 everything
The “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 Steve

Grab Steve’s book The Layoff Journey on Amazon: The Layoff Journey
Learn more at: thestevejaffe.com
Follow Steve on Instagram: @stevejaffethelayoffjourney
Connect 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:

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

🎵 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? 💫

From paralegal to dog psychologist and trainer, meet Hilary Pratt

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 18 Sep 2025 07:00:00 +0000

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

Instagram: @packlovesd
Website: packloveca.com
Wisdom of the Pack Day Camp: wisdomofthepack.com
Instagram (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:

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

🎵 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? 💫

From corporate banking to mother + leadership coach, meet Raina Gandhi

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 11 Sep 2025 07:00:00 +0000

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:

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

🎵 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? 💫

CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 4 Sep 2025 07:00:00 +0000

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 Voyages

Join 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-voyages
Book 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:

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

🎵 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? 💫

From talent acquisition to to Tai Chi instructor, meet Baiba Wisse

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 28 Aug 2025 07:00:00 +0000

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 journeys

Connect with Baiba

Connect with Baiba on LinkedIn: https://www.linkedin.com/in/bwisse/
Listen to The Career in Technicolor
- Apple: https://podcasts.apple.com/us/podcast/career-in-technicolor/id1584835608
- Spotify: 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:

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

🎵 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? 💫

From people operations manager to certified executive coach, meet Natalie Robbins

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 21 Aug 2025 07:00:00 +0000

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 Natalie

LinkedIn: 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:

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

🎵 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? 💫

From corporate banking to career transition coach & recruiter, meet Lori Wallace

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 14 Aug 2025 07:00:00 +0000

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 career
What it’s like to be laid off while on maternity leave
The moment her body forced her to pause and completely reevaluate her life
Why listening to your body’s signals during transition is non‑negotiable
How career change can be one of the most misunderstood (and isolating) forms of modern trauma

If 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:

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

🎵 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? 💫

From donut maker to consumer & CX insights strategist, meet Beth Karawan

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 7 Aug 2025 07:00:00 +0000

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 Cover

When your major doesn’t match your future
Market research, storytelling, and discovering you’re good at math, kind of
What a restaurant job taught Beth about trust and leadership
Letting go of shame around unconventional jobs
Launching “It’s Donut Friday” and leaning into fun
The surprising link between CX and making donuts

Connect with Beth

LinkedIn: https://www.linkedin.com/in/bethcaran
Newsletter: 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:

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

🎵 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? 💫

A corporate sales and thrifted fashion curator, meet Liz Dekofsky

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 31 Jul 2025 07:00:00 +0000

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 bundle

Instagram: 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:

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

🎵 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? 💫

One year of flipping: Cocoon reflections, career chaos & an original song

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 29 Jul 2025 07:00:00 +0000

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 psychic

Trish Jasinski, who bought a chateau in the south of France and left corporate to open a retreat space

Cat 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:

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

🎵 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? 💫

Musicologist to strategic communications advisor, meet Lisa Chensvold

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 24 Jul 2025 07:00:00 +0000

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 world
What it’s like to build a consulting business from scratch
How communications can help shape and reshape organizations at every level
The fear (and thrill) of taking the leap into entrepreneurship

If you’re someone who’s ever felt the nudge to pivot but wondered how your experience translates, this one’s for you.

Connect with Lisa

LinkedIn: 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:

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

🎵 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? 💫

From software engineer to customer experience to AI entrepreneur, meet Mariena Quintanilla

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 17 Jul 2025 07:00:00 +0000

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 leap
Building a financial safety net and jumping anyway
The identity shifts that come with walking away from a title
Why knowing who you are matters more than knowing where you’re going

Mariena 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 Mariena

LinkedIn: 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:

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

🎵 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? 💫

Bathroom tile sales to personal brand & marketing manager, meet Joseph Rudd

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 10 Jul 2025 07:00:00 +0000

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 background
Why networking isn’t as scary as it sounds
The magic of having supportive people in your corner
What to do when self-doubt shows up
How to start building a personal brand—even if you’re not in marketing
Why 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 Joseph

LinkedIn: 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:

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

🎵 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? 💫

From US Navy Captain to Professional Photographer, meet Laura Hatcher

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 3 Jul 2025 07:00:00 +0000

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 life
Finding identity outside the uniform
Imposter syndrome and self-doubt as a creative
Building a business from a side passion
How mentorship and community helped her grow
The emotional side of setting “big” goals
Navigating cultural identity and belonging in new spaces
Adapting through the pandemic and learning as she went

If 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:

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

🎵 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? 💫

From corporate marketing to chateau owner & event curator, meet Trish Jasinski

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 26 Jun 2025 07:00:00 +0000

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 shopping.

And then it happened. She stepped into Château de Gère, a 14th-century stone fortress tucked into the Vallée d’Ossau, and something inside her said, “This is it.”

So she did the unthinkable: she bought it. With no plan. Just heart.

Now, Trish lives in a quiet French village where sheep outnumber people, and she’s turned the château into a beautiful retreat and event space. She’s taken everything she learned from her corporate years and poured it into this new life—this wild, magical, entirely unexpected next chapter.

In this episode, we talk about:

Following a totally unserious whim that changed everything
Why “no plan” doesn’t mean “no purpose”
Using your past experience in completely new ways
Listening to your intuition (even when it makes zero sense)
Creating a life that’s slower, sweeter, and more you

Connect with Trish

Book a stay at Château de Gère: https://chateaudegere.com/
Follow on Instagram: https://www.instagram.com/chateaudegere/

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:

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

🎵 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? 💫

Cocoon Conversation for June 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 24 Jun 2025 07:00:00 +0000

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 aren’t failures, but part of the process, and that confidence is more like a flickering patio light than a spotlight. It’s raw, relatable, and a little unhinged—in the best way.

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:

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

🎵 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? 💫

From software engineer to chocolate maker, meet Case Sandberg

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 19 Jun 2025 07:00:00 +0000

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 something from scratch, and why your next chapter doesn’t need a polished plan — just a little momentum and maybe a glass of chocolate milk.

Whether you're dreaming of leaving tech, craving a more hands-on life, or just want to feel seen in the mess of figuring it all out — this one’s for you.

In this episode, we talk about:

Making a pivot without a perfect plan
Why curiosity can be your compass
Creating a business that feels like you
Burnout, mini-sabbaticals, and trusting the timing
Building something imperfect and still showing up
Letting go of perfectionism to bring people joy

Takeaway quote

“I don’t want to let my perfectionism get in the way of bringing joy to people.”

Connect with Case and San Diego Chocolate Co

Follow on Instagram
Order Online: San Diego Chocolate Co.
Find him at the North Park, Hillcrest, and La Mesa farmers markets

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:

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

🎵 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? 💫

From Guest Experience Manager with Cirque du Soleil to Ghostwriter, meet Carolene Méli

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 12 Jun 2025 07:00:00 +0000

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 shows, and creating magical behind-the-scenes moments for audiences across the globe.

Then—like so many of us—the pandemic flipped everything upside down.

Carolene gets real about what it was like to lose a job she loved, face the uncertainty of solopreneurship, and navigate the deeply humbling moment of asking her parents for financial help. But her story doesn’t stop there. With the help of therapy, community, and a ghostwriting mastermind, she found her footing again—this time, by helping top-tier execs in entertainment shape their personal brand and voice on LinkedIn.

If you’ve ever had to rebuild, reroute, or reinvent yourself completely, this one’s for you. Carolene’s story is packed with honesty, courage, and the kind of hope you might need to hear right now.

Episode Takeaways

Carolene Méli unique career journey from nutrition to ghostwriting
Her 11-year experience with Cirque du Soleil and the leadership and storytelling skills she developed
The impact of the pandemic on her career and the pivot to solopreneurship
The emotional and financial challenges that come with starting over—especially asking for help
The role of therapy in her healing and professional rebirth
How community and collaboration (like a ghostwriting mastermind) helped her grow
Lessons in resilience, reinvention, and letting go of "shoulds"
Why personal branding matters, especially for execs in creative industries

Connect with Carolene

LinkedIn: https://www.linkedin.com/in/carolenemeli/

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:

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

🎵 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? 💫

From politics to nonprofits to executive coach, meet Katie O'Malley

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 5 Jun 2025 07:00:00 +0000

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 that actually cares, and how listening, real, intentional listening, can be the most powerful tool for change.

If you’ve ever felt the nudge to do work that feels more meaningful, or if you're building something new and wondering how to stay aligned with your values, this episode will speak right to you.

What We Talk About:

How Katie’s early work in politics and nonprofits shaped her purpose
Her bold leap into coaching and why it mattered so much
Mental health in the workplace (and why we can’t ignore it anymore)
Building a values-driven coaching business from the ground up
Why listening is the underrated superpower we all need to practice
The messy, joyful reality of flipping your career
Katie’s upcoming TED Talk on the power of listening (happening June 30th in Andover, MA!)

Favorite Quote:

“Listening is more than a soft skill—it’s a radical act of care.”

More from Katie:

Connect on LinkedIn: https://www.linkedin.com/in/kateomalley/
Find Katie and her work at encouragecoaching.org
Follow her on Instagram: @encouragecoaching

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:

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

🎵 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? 💫

From renaissance faire merchant to cartographer, meet Jenna Leveille

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 29 May 2025 07:00:00 +0000

In this episode of The Career Flipper, I chat with Jenna Leveille, who went from working as a merchant in the travelling Renaissance Festival circuit to becoming the Deputy State Cartographer of Arizona and now she’s the VP of State and Local Government Strategy at a mapping company.

But this journey? It’s anything but straight. Jenna’s path weaves through non-traditional college years, a detour into zoology (because saving the world felt like a good place to start), and finally landing in the world of geospatial tech and GIS.

We talk about what it’s like to not have it all figured out, to follow your curiosity, and to keep showing up, even when the next step is unclear. If you’ve ever felt like your career map is a bit...hand-drawn in pencil, this one’s for you. Jenna proves you can absolutely make your own route—and that community, resilience, and a little self-trust can take you further than you imagined.

Connect with Jenna

LinkedIn: https://www.linkedin.com/in/jenna-leveille-1061491b/

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:

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

🎵 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? 💫

Cocoon Conversations: My Career Flip Progress for May 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 27 May 2025 07:00:00 +0000

In this episode of "Cocoon Conversations" on the Career Flipper podcast, I, Jenny Dempsey, take you along on my career journey.

This year, I’ve committed to opening up about my own career flip, just as I encourage my guests to do. So here we are, in May 2025, and I can hardly believe it’s been four months since I started my current day job. It feels surreal to say that, especially considering I was laid off for two years before this.

During this time, I’ve been balancing my full-time job with furniture restoration on the side, dedicating Sundays to it, and squeezing in podcasting and all the related tasks whenever I can. If that sounds overwhelming, it is! Life can be a juggling act, and I know I’m not alone in feeling this way. Scheduling time with friends often feels like a game of Tetris, as we all navigate our busy lives.

I’ve always been the type of person who thrives on variety. I’m the one multitasking—doing laundry while putting away dishes, preparing to record a podcast, creating social media content for my furniture flipping page, and making sure my dog, Dwight, gets outside for a potty break. My brain has always thrived on this mix of activities, and I’ve been like this for as long as I can remember.

Looking back, I’ve come to realize something significant. For a long time, I believed that work—capital W work—was my identity. I thought it was the only thing I was good at. I didn’t believe in taking vacations; if I did, I’d bring my laptop along and continue working. I even had a panic attack in front of a customer service team I was managing because I was so consumed by my job. I poured everything into my work, only to learn the hard way that companies would replace me in an instant. When I was laid off and struggled to find a new job for two years, I was left questioning my identity. Who was I if I wasn’t working?

I dive into this and more in the episode!

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:

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

🎵 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? 💫

From academia to holistic canine nutrition, meet Alexia Mellor

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 22 May 2025 07:00:00 +0000

In today’s episode, we’re talking with Alexia, a holistic canine nutritionist who made an unexpected career flip, thanks to her dog. Alexia started her journey deep in the world of academia and art in the sustainability sector, researching, writing, and painting. But then her dog (yes, her sweet pup, Lucky) flipped her whole life upside down in the best way possible.

Now? She helps dogs thrive, feel better, eat better, and live longer—with a perfect blend of heart, soul, and science. It’s the ultimate plot twist!

We dive into how Alexia transitioned from thinking she was locked into a creative and academic career to discovering her true calling in canine wellness. She talks about embracing discomfort, leaning into the chaos, and the identity shift that comes with going from “I thought I’d be doing X forever” to “Wait, maybe I’m meant to help dogs heal instead?”

We also get into how Alexia created Mystic Dog Mama, her podcast and community focused on holistic pet care and personal growth, all while leaning into the weirdness of following unexpected paths. Whether you’re someone questioning everything or you’re just looking for a little inspiration to follow those furry breadcrumbs in your own life, this episode is for you!

Tune in for a real, raw, and inspiring conversation about career pivots, trusting the process, and following your passion (even when it leads to a totally different destination than you expected).

Takeaways:

It’s okay to embrace discomfort and let it guide you to something new and unexpected.
Career changes often require a full identity shift — from who you thought you were to who you’re meant to be.
Lean into the chaos, trust your gut, and follow the signs (even if they come with paws!).
Community and personal growth go hand-in-hand when navigating big life changes.
Following the breadcrumbs, even if they’re furry, can lead to something beautiful and fulfilling!

Connect with Alexia

Canine Nutrition and Wellness: https://mysticdogmama.com/
Listen to the Mystic Dog Mama Podcast: https://mysticdogmama.com/podcast
Mystic Dog Mama Podcast Instagram: https://www.instagram.com/mysticdogmama/

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:

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

🎵 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? 💫

From psychology to real estate to artist, meet Victoria Tara

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 15 May 2025 07:00:00 +0000

In this episode of The Career Flipper Podcast, host Jenny Dempsey chats with Victoria Tara, a Ukrainian-born contemporary artist based in Miami with a story that’s full of heart, bold choices, and beautiful color (literally and figuratively).

Victoria shares her journey of flipping from a career in psychology and real estate and interior design to becoming a full-time artist. She opens up about the inspiration behind her vibrant paintings, how spirituality and meditation shape her creative process, and why trusting yourself — even when it doesn’t make logical sense — is everything.

She reminds us that every single experience in life, even the ones that feel totally off-track, adds to the story and can help guide us to our true calling. Plus, she gets real about making time for creativity when life is busy, and shares practical tips for artists (and aspiring artists) trying to juggle it all.

Victoria’s story is a powerful reminder that art reflects healing, growth, and self-trust. Her career flip is rooted in deep personal exploration — and her words will resonate with anyone standing at the edge of something new and uncertain.

Episode Takeaways

How art can reflect personal healing and transformation
Why trusting yourself is key when making bold career moves
How meditation can enhance creativity and self-awareness
The beauty of pulling inspiration from life’s toughest moments
Practical ways to make time for art, even with a packed schedule
That balancing multiple careers is not only possible — it can be powerful
The role of spirituality in creating meaningful work
Why art is often just a natural expression of who we are

Connect with Victoria

Art: https://www.victoriatara.com/
Instagram: https://www.instagram.com/victoria.tara.art

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:

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

🎵 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? 💫

From corporate HR to HR consultant, meet Megan Pawlak

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 8 May 2025 07:00:00 +0000

Let’s just say Megan Pawlak did not take the straight path to becoming a powerhouse HR consultant. She started out in food service, rolled through the corporate world, and eventually said, “Yeah... I think I’ll start my own thing.”

Now she runs Benandanti Consulting, helping early-stage startups grow without turning into soul-sucking corporate machines. She’s a pro at finding the right people, saying the quiet parts out loud, and reminding companies that “professional” doesn’t have to mean “emotionally detached robot.”

In this episode, Megan and I get into:

What it’s really like to go solo and start consulting
Why owning your squiggly career path is a total flex
How leaders can stop the talent drain (hint: it starts with respect and ends with not being a jerk)
The outdated workplace vibes we’re leaving behind (bye, “leave it at the door”)

Megan brings the heat, the honesty, and a whole lot of human. Let’s flip the script on work — hit play!

Connect with Megan

LinkedIn: https://www.linkedin.com/in/megan-pawlak-57a975b8/
Benandanti Consulting: https://www.benandanticonsulting.com/
Offline and Unfiltered Podcast: https://www.offlineandunfilteredpod.com/
Substack: https://humanfirstworkplace.substack.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:

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

🎵 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? 💫

From neuroscientist to startup entrepreneur to full-time artist, meet Brian Feretic

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 1 May 2025 07:00:00 +0000

In this episode of the Career Flipper podcast, Jenny Dempsey chats with Brian Feretic about his journey from being a neuroscientist to becoming a resin artist and entrepreneur. Brian opens up about how he dealt with layoffs, found his passion for plants, and even started a social marketplace for plant lovers. He talks about the ups and downs of switching careers, the importance of taking a step back to reflect, and how he rediscovered his love for art. This episode is all about the power of following your passions and seeing career changes as chances to grow and find personal happiness.

Episode Takeaways

A layoff can be the plot twist that leads you to your true passions.
Community and connection are game-changers when navigating a career pivot.
Lean into the unknown—creativity and self-reflection can unlock your next chapter.

Connect with Brian

Instagram: https://www.instagram.com/byunbaej/

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:

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

🎵 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? 💫

Cocoon Conversations: My Career Flip Progress for April 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 29 Apr 2025 07:00:00 +0000

In this April 2025 "cocoon episode" of the Career Flipper podcast, host Jenny, gets real about her own story of jumping back into the corporate world after being laid off. She chats about how she juggles her day job with her creative side gigs and why giving yourself a second chance is so important. Jenny shares those little moments of joy she finds in her weekend projects and opens up about why she decided to add ads to the podcast to help with expenses. Her story is all about change, bouncing back, and figuring out how to handle career twists and turns. Jenny's here to remind us all to embrace our own paths and the magic of fresh starts.

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:

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

🎵 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? 💫

From middle school teacher to furniture restoration, meet Tonya Cassidy

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 24 Apr 2025 07:00:00 +0000

Tonya Cassidy has been a middle school teacher near Piedmont, North Carolina, for her whole career — and she loves her students. But on the side? She’s been running Appaloosa Artisans, her furniture restoration business, creating seriously gorgeous pieces for her clients. And now, with retirement on the horizon, Tonya’s getting ready to take her furniture business full-time — which is kind of wild considering how unexpected this whole path was. But if you’ve seen her work on Instagram, you’d swear this was always the plan.

👉 What you'll get from this episode:

How Tonya went from teaching to furniture flipping (and why that first orbital sander moment was life-changing).
What it’s like being a woman in a male-dominated industry — and how Tonya navigates it with confidence.
Why setting phone boundaries and building genuine connections with clients and fellow flippers is at the heart of her success.

Tonya was actually one of the first flippers I followed after getting laid off, and honestly, she gave me so much hope when I was trying to figure out my next step. I think you’re going to love this one. Hit play and let’s dive in! ❤️

Connect with Tonya

Instagram: https://www.instagram.com/appaloosa___artisans/?hl=en

Facebook: https://www.facebook.com/appaloosaartisans/

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:

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

🎵 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? 💫

From corporate banking manager to house flipper, meet Alex Ferro

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 17 Apr 2025 07:00:00 +0000

In this episode of The Career Flipper podcast, host Jenny Dempsey sits down with Alex Ferro of Winston-Salem, North Carolina. He opens up about his career shift from corporate banking to real estate — and the personal journey that led him there. After his dad passed, Alex started questioning what success really meant to him. He realized that climbing the corporate ladder wasn’t cutting it anymore — he wanted more freedom, more purpose, and a better balance in life.

Alex shares how he navigated the leap into real estate, balancing gut instincts with smart, calculated decisions. He talks about the systems he put in place to stay grounded and how he learned to redefine success beyond just making money. This episode dives into the ups and downs of career transitions — the moments of doubt, the unexpected wins, and the resilience it takes to keep going.

If you’ve ever thought about leaving behind a “stable” job to chase something more meaningful, this one’s for you. Alex’s story is a reminder that success isn’t always about the paycheck — it’s about building a life that feels right.

Episode Takeaways

Switching careers can be a real emotional rollercoaster.
We've all been there, stuck in a job that just doesn't light us up.
Going through personal loss can really shake up how we view our careers and what success means to us.
It's crucial to learn from both the wins and the slip-ups along the way.
Having a solid plan and system in place can really help you get that work-life balance we all crave.
It's all about finding that sweet spot between being spontaneous and making smart choices when it comes to investing.
Success isn't just about the money; it's also about feeling fulfilled and happy with what you do.
Having the freedom to make lifestyle choices can make a huge difference in how satisfied you feel with your career.
Don't be afraid to take risks and shake things up if it means following your passions.
Sharing personal stories can really inspire others to make bold career moves and chase their dreams.

Connect with Alex

Ferro Home Buyers: https://www.ferrohomebuyers.com/
Instagram: https://www.instagram.com/ferrohomebuyers/
Facebook: https://www.facebook.com/Ferrohomebuyers/
LinkedIn: https://www.linkedin.com/company/ferrohomebuyers/
YouTube: https://www.youtube.com/channel/UCEs1Tsbo3gcC_HdvLkmUxIQ

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:

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

🎵 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? 💫

From academia to marketing writer, meet Hannah Slack

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 10 Apr 2025 07:00:00 +0000

In this episode of the Career Flipper podcast, host Jenny Dempsey chats with Hannah Slack, from Sheffield, England. She is a freelance writer who made the leap from academia to marketing. Hannah, who holds a PhD in history, opens up about her journey of stepping away from academia because of mental health challenges and finding her groove in freelance writing. She talks about the early hurdles of freelancing, why patience is key, and how crucial it is to have a support network. The episode dives into themes of self-discovery, tackling self-doubt, and putting mental health first, offering some great insights for anyone thinking about switching up their career path.

Connect with Hannah

LinkedIn: https://www.linkedin.com/in/hannah-slack-phd/
Freelance writing & portfolio: https://topdogwords.co.uk/

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:

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

🎵 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? 💫

From mail carrier to customer experience leader, meet Michael Mattson

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 3 Apr 2025 07:00:00 +0000

Today on The Career Flipper, host Jenny Dempsey is chatting with Michael Mattson, whose career journey is a perfect example of how small, intentional shifts can lead to massive transformations. Michael started out as a mail carrier, delivering letters door to door—and yes, getting to pet all the dogs along the way! But beyond the friendly pups, he saw firsthand the importance of both customer and employee experience, which set him on a path of discovery and career growth.

With a high-empathy mindset, Michael made small leaps that took him from the frontlines of the postal service into a corporate customer experience role, and eventually across the country to become the Manager of Customer Experience for a global organization. He now also serves on advisory boards for multiple CX organizations, helping shape the future of the field.

In this episode, we dive into:

The power of mentorship and why you shouldn’t be afraid to lean on your network
Why employee experience matters just as much as customer experience
The importance of finding the right workplace culture for long-term happiness
How small, calculated risks can open unexpected doors
The delicate balance between career ambitions and personal passions—and why Michael chose to keep photography as a creative outlet rather than a job
How embracing vulnerability at work can strengthen professional relationships

Michael’s story is a reminder that career changes don’t have to happen all at once—sometimes, it’s the little shifts that add up to something big.

Connect with Michael

🔗 LinkedIn: https://www.linkedin.com/in/michaelcmattson/

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:

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

🎵 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? 💫

From corporate marketing to independent publisher, meet Carol Pearson

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 27 Mar 2025 07:00:00 +0000

In this episode, host Jenny Dempsey is sitting down with Carol Pearson from Bay City, Michigan—founder of 10 Little Rules, an independent publishing house. Carol’s career journey has taken plenty of twists and turns. She started in corporate PR and marketing, moved into freelancing, and eventually built her own publishing business. But this conversation isn’t just about career changes—it’s about life changes, too. Carol opens up about navigating divorce, losing both of her parents, and how those experiences reshaped her perspective on gratitude, resilience, and finding meaningful work.

We dive into the emotional side of career transitions—because let’s be real, they’re never just about work. Carol shares how storytelling became a tool for self-discovery, why aligning your career with your values matters, and how to take small, intentional steps toward the life you actually want.

Episode Takeaways

Career transitions are emotional and deeply personal.
Storytelling can be a powerful tool for growth and reflection.
Gratitude and resilience help us navigate life’s toughest moments.
Aligning your work with your values makes all the difference.
Big life changes—like divorce and loss—can completely shift your perspective.
Taking small, actionable steps is the key to pursuing your dreams.
Acknowledging privilege and fostering empathy can shape career decisions.
Staying open to unexpected opportunities can lead to amazing things.

If you’ve ever found yourself at a crossroads, wondering what’s next, this episode is for you. Let’s get into it!

Connect with Carol

Purchase books from the 10 Little Rules collection: https://10littlerules.com/

Use discount code “FLIPME” for 25% off your purchase

LinkedIn: https://www.linkedin.com/in/carolpearson/
Instagram: https://www.pinterest.com/10littlerules/

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:

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

🎵 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? 💫

Cocoon Conversations: My Career Flip Progress for March 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 25 Mar 2025 07:00:00 +0000

In this episode of the Career Flipper podcast, our host Jenny Dempsey gets real about her journey back to full-time work after being laid off for two years. She opens up about the tough times she faced while applying for over 400 jobs and how each rejection hit hard, making her question her identity, which was so tied to her career. Jenny also talks about her adventures in flipping furniture and podcasting, highlighting how important it is to have the mental space to chase your passions. She sees her new job as a solid base that helps her keep dreaming big. Jenny's message to listeners? Embrace your unique career journey and lean on your community for support when you're going through changes.

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:

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

🎵 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? 💫

From model to tech entrepreneur, meet Julie Hanell

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 20 Mar 2025 07:00:00 +0000

In this episode of the Career Flipper podcast, Jenny Dempsey chats with Julie Hanell, who's originally from Switzerland, lived all over and has had quite the diverse career path. Julie's done it all—from modeling to running a coffee shop in South Africa, starting a tech company aimed at empowering women, and working in talent acquisition. Nowadays, she's the head of growth at a global company and also co-hosts the She Hustles podcast, which is all about supporting female entrepreneurs. In this episode, they dive into how Julie has navigated her various career changes, how she makes big decisions, deals with imposter syndrome, and why she believes community and connection are key to growing both personally and professionally.

Episode Takeaways

Julie’s diverse career journey from modeling to entrepreneurship and talent acquisition.
The significance of community and connection in personal and professional growth.
The role of technology in maintaining relationships and facilitating communication.
Decision-making processes and the impact of fear of regret on career choices.
Overcoming imposter syndrome and building self-confidence in professional settings.
The challenges of transitioning from entrepreneurship to corporate roles.
The importance of support networks during career transitions.
Balancing side hustles with full-time employment and managing time effectively.
Insights on the entrepreneurial mindset and its application in corporate environments.
The mission of the She Hustles podcast to empower and inspire female entrepreneurs.

Connect with Julie

Follow her on LinkedIn: https://www.linkedin.com/in/juliehanell/

Listen to She Hustles podcast: https://shehustles.my.canva.site/

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:

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

🎵 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? 💫

Navigating career change: growth, identity and listening to your gut with somatic psychologist, Katie Asmus

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 13 Mar 2025 07:00:00 +0000

Changing careers isn’t just about updating your resume—it’s a big, emotional transition that can shake up your sense of identity, self-worth, and even how you move through the world. In this episode, career flipper host Jenny Dempsey sits down with Licensed Professional Counselor, Katie Asmus, founder and director of the Somatic Nature Therapy Institute headquartered in Boulder, CO, to dive into the rites of passage that come with career shifts, the power of listening to your inner voice, and why change can feel so complicated (but also so rewarding!).

We talk about the grieving process that comes with leaving a job, listening to your body, and why it’s so important to create space for reflection and self-discovery during big life transitions. If you’re in the middle of a career flip (or thinking about one), this episode is packed with wisdom and practical advice to help you move forward with clarity and confidence.

Takeaways

Rites of passage are essential in navigating life changes.
Work identity and self-worth are often deeply connected.
Listening to your inner voice is crucial, but it’s not always easy.

Tune in for a real, honest conversation about the messy, meaningful journey of career change—and how to navigate it with more ease and self-trust.

Connect with Katie

Somatic Nature Therapy Institute: https://www.somaticnaturetherapy.com/
Instagram: https://www.instagram.com/somaticnaturetherapy/
LinkedIn: https://www.linkedin.com/company/somatic-nature-therapy-institute/
YouTube: https://www.youtube.com/channel/UCtm6bTVlnu_hurA-WBwYvFw

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:

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

🎵 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? 💫

From social worker to financial coach, meet Annie Cole

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 6 Mar 2025 08:00:00 +0000

In this episode, host Jenny Dempsey chats with Annie Cole of Vancouver, WA, a financial coach who’s no stranger to career flipping. Annie shares her journey from social work to education, then ed tech, and finally launching her own business focused on financial coaching for women. Along the way, she’s learned the importance of self-care while making intentional career moves. She offers real, practical advice for anyone considering a career change or starting a business—like utilizing free resources, seeking mentorship, and taking it one step at a time. Annie also highlights how bridge jobs can provide financial security and breathing room while you figure out your next step. Whether you're thinking about flipping your own career or diving into entrepreneurship, this conversation is packed with insights on navigating change without being too hard on yourself.

Key Takeaways:

Career changes don’t have to be all-or-nothing—you can transition gradually while keeping financial stability.
Bridge jobs can be a smart way to stay financially secure while exploring your next career move.
Networking and mentorship can open doors you didn’t even know existed.
Taking risks (and even making mistakes) is part of the process—what matters is learning and adjusting along the way.

Connect with Annie

Instagram: https://www.instagram.com/build.wealth.with.annie/
Coaching: https://www.money-essentials.com/
LinkedIn: https://www.linkedin.com/company/money-essentials-for-women/

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:

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

🎵 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? 💫

From corporate R&D to startup growth guiding investors in composites, meet Yannick Willemin

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 27 Feb 2025 08:00:00 +0000

In this episode, host Jenny Dempsey chats with Yannick Willemin, a seasoned expert in the composites industry who’s been at it for 20 years, fueled by his passion for sports. Based in Zurich, Switzerland, Yannick shares how he’s navigated career transitions, embraced change, and built authentic connections along the way. His journey offers valuable lessons for anyone considering a career flip or looking to grow personally and professionally.

Here are some key takeaways from the episode:

Yannick's love for sports led him into the composites field, which creates materials for everything from bicycles to airplanes.
Career transitions require being open to new opportunities and taking time for self-reflection.
Building a strong, authentic network is about forming genuine connections, not pushing sales pitches.
The abilities you gain in previous roles are always valuable when stepping into new ventures.
Sometimes, the biggest hurdle is how we see ourselves. Seeking feedback can help break down those barriers.
Talking about both the highs and lows of your career journey can foster deeper connections and support.
Coaching and mental training are becoming more accepted and valued in the business world.
Embracing change means being willing to learn and thrive in new environments.

Oh, and if you're ever in Paris, Yannick recommends dining at Comme Chez Maman—it’s his favorite spot!

If you're navigating a career change or looking for inspiration, this episode is packed with relatable stories and actionable insights.

Connect with Yannick

https://www.linkedin.com/in/yannickwillemin/

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:

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

🎵 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? 💫

Cocoon Conversations: My career flip progress for February 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 25 Feb 2025 08:00:00 +0000

In this episode of the Career Flipper podcast, host Jenny Dempsey shares her personal journey of transitioning back to corporate life after a period of entrepreneurship and creative pursuits. She discusses the emotional challenges of adjusting to a structured work environment, the importance of finding balance between her corporate job and her passion for furniture flipping, and the ongoing struggle with imposter syndrome. Jenny emphasizes the need for self-compassion during times of change and encourages listeners to embrace their messy career journeys.

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:

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

🎵 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? 💫

From UX designer to furniture maker, meet Ryan Kelly

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 20 Feb 2025 08:00:00 +0000

In this episode of the "Career Flipper" podcast, host Jenny Dempsey interviews Ryan Kelly, who transitioned from a decade-long career in tech to founding Humm Furniture. Ryan shares his journey of creating thoughtful, human-centered furniture and discusses the challenges of this career shift, including time management and overcoming analysis paralysis. He emphasizes the importance of taking action and leveraging his user experience design background. The conversation also highlights the significance of a support system and practical strategies like outsourcing tasks and tracking time to optimize efficiency. Ryan’s story serves as an inspiring example for those considering a career change.

Episode Takeaways

Transitioning from a tech career to entrepreneurship in furniture design.
Challenges of making significant career changes, including time management and analysis paralysis.
The importance of taking action rather than overanalyzing decisions.
The influence of user experience design on furniture creation.
The significance of a support system during career transitions.
Financial considerations and the role of savings in pursuing a new career path.
Strategies for managing a business, including outsourcing tasks.
The value of self-awareness and introspection in shaping career choices.
Practical advice for navigating fear and uncertainty in career changes.
The importance of setting boundaries and being intentional with time allocation.

Connect with Ryan

Hum Furniture: https://humfurniture.com/
Instagram: http://instagram.com/humfurn

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:

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

🎵 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? 💫

From nurse to professional organizer, meet Angelique Beach

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 13 Feb 2025 08:00:00 +0000

In this episode, host Jenny Dempsey chats with Angelique Beach in San Diego, California , who took the leap from nursing to become a professional organizer and founded her own business, Neatly —and what a transformation it’s been!

Angelique unpacks her journey and gets real about the challenges she faced, from feeling unfulfilled in her nursing career to navigating the transition to a business that aligns with her passion. She shares how her support system—family, friends, and a dash of courage—helped her tidy up her path to a new career.

We also dive into the importance of having a financial plan to keep things orderly (literally and figuratively!) while making a career switch. Angelique shares how her nursing background gave her super useful skills for her organizing biz—because who better to bring calm to chaos than a nurse?

Here’s what’s inside this episode:

Filing away job dissatisfaction: How Angelique realized her calling wasn’t in nursing.
Decluttering the fear of change: The steps she took to organize her leap of faith.
Transferable skills are the label makers of career changes: How her nursing skills help her create harmony in her new role.
Finding the right “fit”: Why connecting with ideal clients is key.
Follow your bliss: Why your happiness should never end up in the junk drawer.

If you’ve ever felt stuck in your current role and wondered if it’s possible to sort out a career that brings you joy, this episode is for you. Angelique proves that it’s never too late to tidy up your dreams and live the life you deserve.

If you’re curious about what it takes to flip your own career or just love hearing transformation stories, you’re in the right place. Don’t forget to subscribe for new episodes every Thursday!

Connect with Angelique

Check out her business: https://helloneatly.com/
Follow her on Instagram: https://www.instagram.com/helloneatly

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:

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

🎵 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? 💫

From engineering to personal branding & marketing consultant, meet Ghalib Hassam

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 6 Feb 2025 08:00:00 +0000

In today’s episode, host Jenny Dempsey chats with Ghalib Hassam, who shares his inspiring story of going from pursuing a master’s in engineering in Pakistan to starting his own business in marketing and personal branding in the UK.

Ghalib opens up about:

Navigating imposter syndrome and complex family dynamics.
Why taking risks and putting yourself out there is always worth it.
How his engineering background gave him a unique edge in his new career.
His big dreams of building an audience and launching a podcast.

Ghalib’s journey is a powerful reminder that stepping out of your comfort zone can lead to incredible opportunities—and sometimes, all it takes is asking.

If you’re curious about what it takes to flip your own career or just love hearing transformation stories, you’re in the right place. Don’t forget to subscribe for new episodes every Thursday!

Connect with Ghalib

LinkedIn: https://www.linkedin.com/in/ghalibhassam/
Ghalib’s Personal Branding & Marketing Company, Baghi: https://www.linkedin.com/company/baghi-consultancy/about/
The Founder Lore Podcast: https://www.youtube.com/playlist?list=PL0m3ZDJ5I48srKkYnNVm6kb092F78GxKK

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:

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

🎵 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? 💫

From wedding planner and photographer to S’mores Cart entrepreneurs, meet Elyse Rowen and Kelley Williams

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 30 Jan 2025 08:00:00 +0000

In this episode, host Jenny Dempsey sits down with Elyse Rowen and Kelley Williams, two unstoppable entrepreneurs who both run their own individual companies of planning weddings and capturing moments behind the camera to creating a luxury dessert experience with The S'mores Cart in San Luis Obispo, California.

It all started with a lightbulb moment during a road trip to Disneyland. But turning that idea into a successful business wasn’t all marshmallows and chocolate. Elyse and Kelley share the highs and lows of building their dream, from their first disastrous event to crafting unforgettable s’mores experiences for their customers.

These two best friends prove that with passion, resilience, and a sprinkle of creativity, failure is just fuel for the fire. Their story is packed with inspiration for anyone thinking about flipping careers, starting a business, or simply chasing a dream.

Takeaways:

There’s something beautiful—and scary—about needing to make it work.
Failure is just fuel for their fire.
The journey of entrepreneurship is full of unexpected challenges.
Having a supportive team is crucial for success.
Resilience is key when facing setbacks.
Creating a unique experience can set your business apart.
Friendship can strengthen business partnerships.
It’s important to have a clear vision and goals.
Taking breaks can help refresh your passion.
Investing in your business requires time and money.

Connect with The S'mores Cart

Don’t miss this inspiring episode filled with grit, gooey marshmallows, and the magic of friendship!

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:

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

🎵 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? 💫

Cocoon Conversations: My Career Flip Progress for January 2025

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 28 Jan 2025 08:00:00 +0000

In this heartfelt Bonus Cocoon episode of The Career Flipper podcast, Jenny Dempsey takes you behind the scenes of her personal career-flipping journey. From 18 years in customer service to unexpected layoffs, she shares how resilience, rejection, and a dash of creativity led her to furniture flipping, podcasting, and rediscovering her purpose.

Jenny reflects on lessons from her past, including the impact of her father’s advice and the challenges of starting over. She opens up about her new job opportunity, the financial ups and downs, and her evolving goals. This episode is a candid reminder that change is messy but worth it, and resilience is the glue that holds it all together.

Tune in for real talk, inspiration, and maybe a few laughs along the way! Don’t forget to subscribe and join the journey.

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:

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

🎵 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? 💫

From car sales and after school teacher to furniture flipper, meet Mariah Howard

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 23 Jan 2025 08:00:00 +0000

In this episode of The Career Flipper podcast, host Jenny Dempsey chats with Mariah Howard of Murrieta, California, a former teacher and sales professional who took the leap to become a full-time furniture flipper. Mariah shares her inspiring journey of leaving a traditional job to follow her passion for furniture restoration.

Here’s what you’ll hear about in this episode:

How Mariah transitioned from teaching and sales to full-time furniture flipping.
Her experience on the competition show The Flip-Off and how it shaped her journey.
The chaos (and rewards!) of balancing a business with family life.
Her creative, budget-friendly strategies for starting a business with minimal investment.
Why community support is a game-changer for entrepreneurs.
Real talk about overcoming fears, giving yourself grace, and trusting your gut as you build your dream.

If you’ve ever wondered how to turn your side hustle into your main gig or need a dose of inspiration to follow your passion, this episode is for you!

🎧 Tune in now to hear Mariah’s story and get motivated to flip your own career! Don’t forget to subscribe and leave a review—it helps more career flippers find the show!

Connect with Mariah Howard

Instagram: https://www.instagram.com/mariahflipsfurniture/
YouTube: https://www.youtube.com/channel/UCwskLG8m5oSZBlO_z5h_eKw
Facebook: https://www.facebook.com/mariahflipsfurniture/

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:

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

🎵 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? 💫

From corporate marketing & advertising to Caribbean bartender, meet Matthew Smith

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 16 Jan 2025 08:00:00 +0000

Welcome to the first episode of Season 2 of The Career Flipper Podcast!

Host Jenny Dempsey kicks things off with career flipper Matthew Smith.

Matthew went from working in corporate advertising in New York City to bartending in the Caribbean. Yep, you read that right! After losing his job right before COVID, struggling to find a new one, and going through a tough breakup, Matthew ended up moving back home and living in his parents’ basement. But then, a “temporary” job in St. John, U.S. Virgin Islands, came up to help cover his NYC rent. Well, four years later, he’s still in the Caribbean, finding happiness and community he never expected.

In this episode, Matthew shares how he made that huge leap, what it was like to leave the city life behind, and how he found a community that helped him grow. He talks about the challenges, the surprises, and why taking risks—despite the fear—can lead to some pretty amazing opportunities.

Takeaways:

Life either throws you a curveball, or you make a decision to change.
Big challenges can lead to big opportunities.
Matthew realized he was becoming a version of himself he hadn’t seen in a long time.
Happiness matters more than just making money.
Give yourself some grace—things don’t always need to be perfect.
Losing his job turned out to be a blessing in disguise.
It’s okay not to have everything figured out—sometimes you just have to go for it.
A strong community can really help you grow and keep you going.
Think about what you loved as a kid to help find your passion.

Connect with Matthew

Instagram: https://www.instagram.com/matthewhs7

This episode is all about taking a leap, embracing change, and finding unexpected happiness. It’s a great listen if you’re thinking about making your own career flip or just need a bit of inspiration to get started. Grab a drink, get comfy, and enjoy!

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:

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

🎵 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? 💫

Get Ready for Season 2 of The Career Flipper!

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 9 Jan 2025 08:00:00 +0000

Welcome to Season 2 of The Career Flipper! In this episode, host Jenny Dempsey kicks off the new season with a sneak peek into what’s coming your way. Expect more real stories from people around the world who’ve made career changes, from all industries and backgrounds. Jenny dives into the ups and downs of career flips, including personal struggles, wins, and advice you can actually use to make your own transition smoother.

In this season, we’ll explore topics like:

How to figure out what’s next when you’re feeling totally stuck
How to know if it’s the right time to take the leap or play it safe
Managing money while chasing a new career path

Jenny’s in the middle of her own career flip and shares how every conversation with her guests helps her keep moving forward, even when things get tough. Tune in for stories, advice, and the real behind-the-scenes of career changes.

Important Links:

Subscribe to the podcast so you don’t miss any future episodes!
Want to share your own career flip story? Email Jenny at hello@thecareerflipper.com to be featured in a future episode.
Follow the show on Instagram: @thecareerflipperpod

Don’t forget to subscribe and share this episode with someone who might be ready for their own career flip!

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:

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

🎵 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? 💫

2024 Podcast recap: what I’ve learned so far from career flippers from around the world

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 17 Dec 2024 08:00:00 +0000

In this episode, host Jenny Dempsey reflects on the journey of her podcast, 'The Career Flipper,' sharing insights gained from interviewing various guests who have successfully navigated career changes. She discusses the importance of finding one's calling, transferring skills from past experiences, taking calculated risks, and the necessity of continuous learning and adaptation. Jenny emphasizes the significance of overcoming fear and self-doubt while balancing practical needs with the pursuit of dreams. The episode concludes with a message of encouragement for listeners to stay curious and brave as they embark on their own career journeys.

Takeaways

The podcast started from a dream and a desire to connect.
Hearing others' stories can normalize the messy journey of career changes.
Your calling evolves and may be right under your nose.
Skills from past jobs are transferable to new opportunities.
Calculated risks are essential in career transitions.
Learning and adapting are crucial for growth.
Fear and self-doubt are common but can be overcome.
Balancing practical needs with dreams is important.
It's okay to take traditional roles while pursuing passions.
Stay curious and brave on your career journey.

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:

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

🎵 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? 💫

From sales account executive to certified professional coach, meet Marina Movsissian

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 12 Dec 2024 08:00:00 +0000

What if you have a successful six-figure career but still don’t feel fulfilled? That’s exactly what Marina Movsissian from Paris, France, experienced. In this episode, Marina shares her journey from a thriving marketing and sales career, including time with Google in Dublin and San Francisco, to starting her own coaching business, EmpowerMov. While juggling her full-time job, Marina began helping women in leadership through workshops, 1:1 coaching, and speaking events—work she now does full time.

Beyond her career flip, Marina reveals how dance has been a transformative part of her story, helping her build the creativity and confidence she brings to her work and life. Her story reminds us that even when a career seems picture-perfect, it’s okay to seek something deeper. Sometimes, your next chapter is quietly waiting for you—you just need the courage to say yes.

Episode Takeaways

Confidence allows us to take space and shine together.
Career flips can happen gradually, not just in one leap.
Dance has therapeutic qualities that enhance personal growth.
Coaching can help individuals discover their true desires.
It's important to prioritize self-development as a coach.
Women often face societal pressures that limit their self-expression.
Fulfillment can come from various aspects of life, not just work.
Trusting the process is key to finding one's path.
Work-life balance is essential for overall well-being.
It's okay to have multiple passions and interests outside of work.

Connect with Marina

LinkedIn: https://www.linkedin.com/in/marinamovsissian-coach/
Coaching: https://en.empowermov.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:

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

🎵 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? 💫

From high school English teacher to owner of E-WRITE, writing training consultancy, meet Leslie O’Flahavan

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 10 Dec 2024 08:00:00 +0000

Have you ever been asked by your boss to take on something totally outside your job description, and then suddenly, you’re discovering a whole new skill or side of yourself? It’s funny how these little pivots can change everything about how we see our potential.

Meet Leslie O’Flahavan! She’s someone who didn’t make a huge leap, but instead slid her career forward, moving from nine amazing years as a high school English teacher to becoming the owner of E-WRITE Online, a training consultancy where she speaks and teaches writing workshops for Fortune 500 companies, government agencies, and nonprofits around the world. She’s even a LinkedIn Learning instructor with six courses and created the “Bite, Snack, and Meal” approach to web content writing (she’s got a Wikipedia page to prove it!).

In this episode, Leslie shows us that a career shift isn’t about ditching everything you know—it’s about putting your skills to use in new ways. She shares how going into new roles with an open mind (and asking for help when you need it!) can make all the difference. You might find that you already have all the courage you need to pivot, whether it’s a small tweak or a big change.

Connect with Leslie

Learn more about the services she offers with EWRITE: https://ewriteonline.com/
Her LinkedIn: https://www.linkedin.com/in/leslieoflahavan/

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:

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

🎵 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? 💫

From perinatal genetics counselor to SaaS customer experience manager, meet Lauren Rose Eimers

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 5 Dec 2024 08:00:00 +0000

How do you navigate a career pivot as a new parent, especially when you realize your old job, that you still love, just doesn’t fit your life anymore?

In this episode, you’ll meet Lauren Rose Eimers from Boise, Idaho, who’s been on a winding career journey, moving from mental health to genetic counseling and ultimately to customer experience leadership in the tech startup world. We dive into her “one foot in, one foot out” approach to taking calculated risks, the importance of finding small moments of joy in daily work, and how becoming a parent reshaped her career priorities. Lauren shares her insights on balancing work and family, the highs and lows of big career changes, and how dreaming big and taking bold steps can lead to a truly fulfilling career.

Connect with Lauren Rose

LinkedIn: https://www.linkedin.com/in/lauren-rose-e/
Coaching: https://perfectedpath.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:

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

🎵 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? 💫

From corporate communications specialist to career change author, meet Kathleen Goggin

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 3 Dec 2024 08:00:00 +0000

Have you ever had a really good job, maybe even your dream job, take a turn for the worse?

I’m so excited to welcome Kathleen “Kate” Goggin! Kate’s a pro at navigating career changes, and she’s here to share her journey and some hard-earned insights on making career shifts work for you. Kate’s background is wide-ranging—she’s worked in radio and TV production, web writing, outreach, media affairs, and consulting. She’s taken all the lessons learned from those ups and downs, along with her experiences within her life outside of work: moving, raising a family, health and caretaking, and poured them into her book, “10 Little Rules When Good Jobs Go Bad”, a guide to help people handle tough job situations. Kate’s all about self-awareness, compassion, and community support when it comes to creating fulfilling career paths, and I think you’re going to love her perspective!

Connect with Kathleen

LinkedIn: https://www.linkedin.com/in/kategoggin/
Learn more about Kathleen on her website: https://kategoggin.net/
Purchase her book, “10 Little Rules When Good Jobs Go Bad”
Also available on Amazon

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:

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

🎵 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? 💫

A short story + personal message from Jenny Dempsey

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 26 Nov 2024 08:00:00 +0000

Have you ever had a project that just didn’t go as planned? In this episode, Jenny Dempsey shares a personal story about a furniture project that didn’t quite work out the way she hoped—but ended up creating a great opportunity for someone else.

She dives into the lessons she learned from this setback and highlights the importance of community and support during tough times.

Jenny reminds us that life often takes unexpected turns, and it’s all about embracing those changes and staying open to new possibilities. She wraps up with a big thank you to her listeners for the connections and shared experiences that make this journey so special.

And, stay tuned for Season 2 premiering January 16th, 2025.

Connect

Contact me to share your story on a future episode: https://www.thecareerflipper.com/contact

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:

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

🎵 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? 💫

From corporate marketing to pet waste management entrepreneur, meet Courtney Copeland

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 21 Nov 2024 08:00:00 +0000

Have you ever walked down the street and spotted a pile of dog doo just sitting there? Even with doo-doo bags available from the city or apartment complex, some folks just don’t bother to pick it up. It's gross, right? And let's be real—nobody wants that mess ending up on their shoes!

Now, let me introduce you to Courtney Copeland. She made a big career change, leaving her corporate marketing job after over a decade to start her own dog waste removal service, SD Scoop Squad, in sunny San Diego, California.

Courtney's journey is pretty inspiring! She shares how her love for dogs and her desire to tackle this “crappy” problem led her to her next career step. You might think, “Isn’t that a bit bougie? Can’t people just pick up after their pets?” But you’d be surprised at how many people genuinely need this service. Whether it's someone with a disability who can't bend down or just folks who can’t be bothered to use the free bags provided in their apartment complexes, there’s a real need out there.

Courtney is out there making a difference, one scoop at a time, and helping pet owners keep their spaces clean and enjoyable. It's all about turning a problem into an opportunity and making life a little easier for everyone.

Connect with Courtney

Learn more about SD Scoop Squad & book your service: https://www.sdscoopsquad.com/
Follow SD Scoop Squad on Instagram: https://www.instagram.com/sdscoopsquad
Connect on Facebook: https://www.facebook.com/sdscoopsquad

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:

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

🎵 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? 💫

From Ethics ThD to tech program manager, meet Julie Morris

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 19 Nov 2024 08:00:00 +0000

What happens when the career you’ve spent decades working toward doesn’t turn out the way you expected?

In this episode, Julie Morris from Seattle, Washington shares her career flip story of shifting from academia, where she received her doctorate in ethics and worked as a professor, to a whole new path in tech as a program manager. She opens up about facing a toxic work environment and how it led her to question her long-term plans. Julie talks about the importance of staying open to change, recognizing the value of transferable skills, and taking a leap into something completely different when your original plan no longer fits. Plus, she offers practical tips on how to explore new opportunities, from making a list of your interests to connecting with others in fields you’re curious about.

Episode Takeaways

Don't be afraid to explore different career paths and be open to new opportunities.
Recognize the transferable skills gained from previous experiences and how they can be applied in new environments.
Make a list of interests and curiosities to guide your exploration.
Connect with people in fields of interest to gain insight and support.

Connect with Julie

LinkedIn: https://www.linkedin.com/in/juliermorris/
Instagram: https://www.instagram.com/juliermorris

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:

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

🎵 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? 💫

From nursing to woodworking, meet Jake Conneen

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 14 Nov 2024 08:00:00 +0000

How do you know when it's time to make a big career change, even if you're not sure what’s next?

In this episode, I’m excited to reconnect with Jake Conneen, who I know from high school in the little Southern California town we grew up in, Norco. Now based in El Paso, Texas, Jake shares his wild ride of career flips—from construction to journalism, restaurant management, the military, nursing, and now running his own woodworking biz, Doby’s Craft House, named after his dog. Jake’s all about taking smart risks and following what truly makes you happy, even if it means flipping careers more than once. He opens up about how the stress shifts when you start working for yourself, and why self-care and time management are a game-changer. And to keep it real about how we juggle all the things, you may also hear his daughter, Rosemary, in the background during the episode! He’s leading by example for her, showing the importance of chasing passions and making her own choices.

If you’ve been thinking about a career flip but aren’t sure how to take the leap, Jake’s story will definitely inspire you!

Episode Takeaways

Taking calculated risks and following what makes you happy can lead to fulfillment in your career.
Working for yourself can bring a different kind of stress, but it can also provide a sense of control and fulfillment.
Self-care and time management are crucial when juggling multiple responsibilities.
Setting an example for your children by pursuing your passions and making your own choices can inspire them to do the same.

Connect with Jake

https://www.dobbyscrafthouse.com/

Instgram: https://www.instagram.com/dobbyscrafthouse/

YouTube: https://www.youtube.com/@dobbyscrafthouse

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:

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

🎵 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? 💫

From head of marketing to visual artist, meet Galina Marcus

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 12 Nov 2024 08:00:00 +0000

Have you ever stopped to really listen to what your body and mind are telling you about your work? In this episode, Galina Marcus shares her career flip story, and it’s full of valuable lessons. She started in the fashion industry in Russia, then moved into marketing in the tech world, but eventually, she made the choice to follow her passion for art. Now, she's not only a visual artist and podcast host of In the Art Scene Podcast but also the founder of the San Diego Art Directory, a nonprofit that supports local artists.

Galina’s story is a reminder to listen to yourself and make changes when necessary, even when it's scary. She talks about the power of following your passions and building a career that truly reflects your values. And along the way, she found real fulfillment by connecting with others in her field and creating a supportive community. Her journey also shows us that it’s never too late to pivot and try something new, even if it means starting from scratch.

Episode Takeaways

Listen to your body and make changes when necessary, even if it's scary.
Follow your passions and create a career that aligns with your values.
Building a community and connecting with others in your field can be incredibly fulfilling.
Don't be afraid to pivot and try new things, even if it means starting from scratch.

Connect with Galina

San Diego Art Directory
- Website: https://sandiegoartdirectory.com/
- Instagram: https://www.instagram.com/sandiegoartdirectory/
In the Art Scene Podcast
- Website: https://intheartscene.com
- Instagram: https://www.instagram.com/in_the_art_scene/
Galina’s Artwork
- Website: https://galinamarcus.com/
- Instagram: https://www.instagram.com/galinamarcus_art/

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:

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

🎵 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? 💫

From CPA/CFO/finance leader to executive and leadership coach, meet Ricky Padgett

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 7 Nov 2024 08:00:00 +0000

Ok, quick question for you: Ever feel like your work and identity are all tangled up?

Today, we’re chatting with Ricky Padgett from Burlington, Vermont. He’s a certified executive and leadership coach, and he’s been there. In this episode, Ricky shares his career flip story—from being a CFO to still doing CPA work, while coaching others to navigate their own big career changes. He talks about how staying true to your values is key when making those big decisions. Plus, he highlights the power of asking for help when you're going through change. Spoiler alert: you don’t have to figure it all out alone! Ricky also opens up about the challenge of separating who you are from what you do—and why it’s so important to give yourself permission to redefine what success looks like for *you.*

And for listeners of The Career Flipper podcast, Ricky’s offering a 20% discount on his coaching program!

Episode Takeaways

Values play a crucial role in guiding career decisions and can serve as anchors during times of change.
Asking for help is a superpower that can lead to support, growth, and stronger relationships.
Untangling one's identity from their work is a challenging but necessary process when making a career flip.
Giving oneself permission to redefine success and follow a different path is essential for personal and professional growth.

Connect with Ricky

https://www.padgettcoaching.com/

Mention The Career Flipper Podcast for 20% off a 3-month coaching package!

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:

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

🎵 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? 💫

From Corporate COO to General Contractor & Interior Designer, meet Kendra Roy

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 31 Oct 2024 07:00:00 +0000

What would you do if you weren’t afraid of failing?

In this episode, we hear from Kendra Roy, an incredible interior designer and general contractor in San Diego, California, about her journey from working a stable job to starting her own business. She opens up about the real challenges she faced—especially in gaining respect as a woman in the construction world—and how building strong relationships became key to her success. Kendra also gets real about the fear and self-doubt that comes with leaving a secure role to chase a new venture and the importance of having a solid support system in place.

If you're considering a career change, Kendra’s advice is to take calculated risks and stay the course, even when things get tough. It's all about perseverance and trusting that you’re on the right path.

Episode Takeaways

Building relationships and gaining respect are crucial in any industry.
Having a support system is important for navigating the challenges of starting a new venture.
Taking calculated risks and pursuing your dreams can lead to personal and professional fulfillment.
Self-doubt is common, but it's important to remember your unique value and capabilities.
Perseverance is key in overcoming obstacles and achieving success.

Connect with Kendra

Kendra Roy Designs main website: https://kendraroydesigns.com/
Connect on Instagram: https://www.instagram.com/kendraroydesigns/

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:

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

🎵 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? 💫

From corporate head of sales & marketing to startup founder, meet Tushar Jain

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 29 Oct 2024 07:00:00 +0000

Ever wondered what it’s like to step away from the comfort of a steady corporate job and dive headfirst into the whirlwind of founding your own startup, where you’re suddenly the one wearing all the hats?

Meet Tushar Jain from India. He is the founder of Enthu.ai, a software designed to help coach sales and customer service agents, improving overall customer experiences. Tushar didn’t just flip his career once—he’s done it twice. First, he left his stable enterprise job to join a startup in a completely different city. Then, he took the ultimate leap and became a full-time founder of his own tech startup. His journey is all about taking risks, embracing change, and finding the non-financial rewards in entrepreneurship, like more control over his time and being able to spend quality moments with family.

Episode Takeaways

Take calculated risks and change your mindset when making career transitions.
Thoroughly research and validate business ideas before starting a venture.
Embrace the non-financial gains of entrepreneurship, such as time flexibility and personal growth.
Lean on your network and ask for help when needed.

Connect with Tushar

LinkedIn: https://www.linkedin.com/in/tushj/
Check out his company + tell them you heard about it on The Career Flipper: https://enthu.ai/

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:

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

🎵 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? 💫

From baker & pastry chef to global CX leader, meet Luke Jamieson

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 24 Oct 2024 07:00:00 +0000

What can baking bread and pastries teach you about working in the customer experience tech space? In today’s episode, host Jenny Dempsey introduces you to Luke Jamieson from Melbourne, Australia. He started out as a baker and pastry chef, wrangled some cattle, tried his hand at graphic design, and eventually discovered his true passion in the customer experience (CX) world. Luke shares how curiosity has shaped his journey and reminds us that careers don’t need to follow a straight line—you can find creativity in any job. He also talks about how hands-on experience often trumps academic degrees and why it’s so important to align your work with what truly matters to you.

Episode Takeaways

Curiosity and openness to new opportunities shape your career.
Creativity can be found in any job, not just traditionally creative roles.
You can learn valuable lessons from every experience, no matter how small.
Finding time for what you love is essential for personal growth.

Connect with Luke

LinkedIn: https://www.linkedin.com/in/luke-jamieson/

His main website: https://www.lukejamieson.live/

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:

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

🎵 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? 💫

From behind the corporate desk to out in the field as a CBS LA Sports Anchor, meet Chris Hayre

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 22 Oct 2024 07:00:00 +0000

Are you a sports fan curious about how to make the leap from a corporate desk to the field, reporting on the games you love?

In this episode of The Career Flipper podcast, host Jenny Dempsey chats with Chris Hayre, a CBS LA Sports anchor and reporter and creator of the Los Angeles Chargers weekly podcast about his transition from corporate marketing with the Los Angeles Lakers to sports media. They dive into the importance of setting clear goals, overcoming obstacles, and having a strong support system. Chris shares his journey of taking risks, building confidence, and discovering joy in the process of career flipping. He also offers insightful advice for anyone thinking about a career change, reminding us to stay connected to our "why" and enjoy the journey!

Connect with Chris

X: https://x.com/chrishayre
Instagram: https://www.instagram.com/chrishayre/
Also referenced in the episode, shout out to Ty: https://www.instagram.com/tynowell/

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:

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

🎵 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? 💫

From geographer to public speaker & trainer, meet Frank Winters

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 17 Oct 2024 07:00:00 +0000

Feeling stuck in your career, or are you keeping an open mind? In this episode, Frank Winters from Schenectady, NY, shares his incredible career flip. After 35 years as New York State's Geographic Information Officer (GIO) and holding leadership roles like Executive Director of the Geospatial Advisory Council, Frank decided to pivot. Now, as the owner of WintersGeo Inc., he's all about public speaking workshops, communication coaching, and geospatial consulting.

Frank dives into the power of following your "North Star," making decisions that open new doors, and embracing curiosity to grow. His story is all about finding fulfillment through work that truly clicks with who you are.

He’s also the author of 10 Little Rules for Sharing Your Story, runs public speaking workshops, and even coaches a youth mountain bike team.

Episode Takeaways

Follow your North Star and make decisions that open new doors.
Embrace curiosity and continuous learning to grow in your career.
Find fulfillment through work that aligns with your values and brings you joy.
Leave the world a better place by making a positive impact in your work and interactions.
Approach feedback with curiosity and a growth mindset.

Connect with Frank

LinkedIn: https://www.linkedin.com/in/frank-winters-gio/

Buy his book, 10 Little Rules for Sharing Your Story: https://10littlerules.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:

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

🎵 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? 💫

From VP of Sales in manufacturing to workplace trauma coach, meet Rob Connelly

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 10 Oct 2024 07:00:00 +0000

What can we learn from micro-pivots, those little hop, skips and cookie crumbs we take and leave on the path as we navigate our career?

In this episode, we meet Rob Connelly from Charleston, South Carolina, who went from VP of Sales in the manufacturing industry to starting his own business as a workplace trauma coach. Rob’s journey started with helping turn around his cousin’s window and door business, which sparked his love for problem-solving and team development. Over the years, he’s made several micro-pivots, testing out different industries and roles, all while finding the work that truly aligns with his values and passions.

Rob opens up about the power of reflecting on your values, being honest with yourself, and how side jobs and hobbies can help you explore new interests before making a full leap. He’s proof that sometimes, multiple career flips are exactly what you need to grow personally and professionally.

If you're feeling stuck or looking for inspiration to make your next move, Rob's story is full of takeaways on designing a fulfilling work life, especially when it comes to addressing and healing from workplace trauma.

Connect with Rob

LinkedIn: https://www.linkedin.com/in/rob-connelly/

Turnstile Coaching: https://turnstilecoaching.com/professional-coaching/

Rob’s Music: https://robconnellymusic.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:

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

🎵 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? 💫

From nutritionist to software developer, meet Danielle Lewis

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 8 Oct 2024 07:00:00 +0000

Have you ever felt like your career path just wasn’t the right fit, even after putting in years of effort?

In this episode, you’ll meet Danielle Lewis, a Texas native who’s been living in Barcelona, Spain for 12 years. Career flipping is practically in her DNA, and she shares her journey of making bold choices to shape her own path. Danielle started out as a nutritionist, but soon realized it wasn’t her calling. After several career flips—from moving abroad and teaching English to working in customer support and product management—she’s now in the middle of yet another transition. After taking some time off, Danielle decided to pursue software development and is currently enrolled in a bootcamp. Throughout her journey, she’s wrestled with feelings of guilt, shame, and fear of judgment.

Episode Takeaways

It's okay to change careers and pursue different paths if you're not fulfilled
Feelings of guilt and shame are common when making career changes, but it's important to prioritize your well-being
Taking time off to rest and reflect can help in unraveling your thoughts and making decisions
Courage and creativity are necessary when pursuing unconventional career paths
It's important to listen to your own desires and not worry too much about what others think

Connect with Danielle

LinkedIn: https://www.linkedin.com/in/adaniellel/

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:

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

🎵 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? 💫

From real estate & law enforcement to founding Cucina di Pizza, meet husband and wife team, Ashley & Tony Ross

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 3 Oct 2024 07:00:00 +0000

What challenges could come up when you turn your passion into a business?

In this episode, your host Jenny Dempsey chats with Ashley and Tony Ross, the dynamic duo behind Cucina de Pizza in San Diego, California. They share their incredible journey of leaving behind their careers in real estate and law enforcement to dive headfirst into the pizza business. Ashley and Tony started by perfecting their pizza recipes and using Instagram to build a loyal following, one delicious slice at a time.

But the road wasn’t always smooth. They faced challenges and setbacks, but their resilience and commitment to delivering a top-notch product and exceptional customer service kept them going. Now, Cucina de Pizza is known for its creative and mouthwatering toppings like biscuits and gravy, barbecue chicken, jalapeño popper, and a variety of veggie options.

Ashley and Tony’s story is a testament to the power of taking risks and pursuing your dreams, no matter how unconventional the path may seem. Tune in to get inspired and maybe even get a little hungry!

Episode Takeaways

Take risks and expect rejection when pursuing a career flip.
Document your journey and learn from both successes and failures.
Focus on providing a quality product and outstanding customer service.
Use social media, like Instagram, to build a following and connect with potential customers.
Embrace challenges and setbacks as opportunities for growth and improvement.
Offer unique and delicious options to stand out in the market.
Believe in yourself and your product, even in the face of imposter syndrome.
Stay positive and learn from every experience, both positive and negative.
Connect with your community and build a loyal customer base.
Follow your passion and take the leap to pursue your dreams.

Connect with Cucina di Pizza

https://www.instagram.com/cucinadipizza/

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:

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

🎵 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? 💫

From music teacher to baker, meet Cat Cheng

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 1 Oct 2024 07:00:00 +0000

What does it take to leave a job you love, even when you know it’s no longer the right fit for your health? In today’s episode, we chat with Cat Cheng from New York—who you might know from Netflix’s "Blue Ribbon Baking Championship". Cat made the bold switch from being a music teacher to becoming a successful home baker and content creator. She opens up about the challenges of her career change, including how COVID-19 impacted her journey and the struggles she faced with narcolepsy. Cat also shares how essential support from her loved ones has been, what it’s like to find your identity beyond your career, and how competing on Netflix was a game changer. She’s got solid advice for anyone thinking about a career flip, emphasizing the power of community and self-acceptance in the creative process.

Episode Takeaways

Cat's baking journey began with a simple apple pie.
She emphasizes the importance of identity beyond one's profession.
Cat experienced imposter syndrome while competing on Netflix.
Consistency in content creation is key to success.
She encourages others to embrace their unique journeys.
Community support is vital during career transitions.
Time management is essential for balancing multiple roles.

Connect with Cat

Follow her personal Instagram: https://www.instagram.com/itscatcheng
In NY? Order from her drool-worthy bakery: https://www.instagram.com/catsbakesny
See what tasty food she’s enjoying: https://www.instagram.com/catzeatz
Check out her YouTube channel: https://www.youtube.com/channel/UCii1s41Xzf_VadAMTIN6ABQ

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:

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

🎵 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? 💫

SaaS sales director to divorce therapist, meet Jason Scriven

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 26 Sep 2024 07:00:00 +0000

What if you took something really tough you went through and turned it into a way to help others going through the same thing? That’s exactly what Jason did. He went from dreaming of a baseball career to working as director of sales in the SaaS world, and then made a huge shift to becoming a men's divorce therapist. After facing his own difficult divorce, Jason realized he wanted to support others navigating similar challenges. He talks about how important it is to seek help during hard times and stay true to yourself in your work. If you're thinking about a career flip, Jason’s advice is to start small and pursue your passions on the side. He even shares a cool story about a golf caddy who turned his love for the game into a successful podcast and book, all while keeping his day job.

Episode Takeaways

Don't wait to pursue a career flip; start taking steps towards your passion now.
Seek support and professional help during challenging times.
Authenticity and personal experience are valuable assets in coaching.
You can start pursuing your passion on the side while still working your day job.

Connect with Jason

https://www.scrivenprogram.com/
Twitter: https://www.twitter.com/thejasonscriven
Instagram: https://www.instagram.com/divorce101_
LinkedIn: https://www.linkedin.com/in/jasonscriven/

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:

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

🎵 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? 💫

Customer service agent to licensed electrician, meet Jeff Watkin

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 24 Sep 2024 07:00:00 +0000

Ever wondered what it’s like to go from customer service to becoming a licensed electrician in Spain? Join me as I chat with Jeff Watkin about his inspiring journey from California to Barcelona, where he traded in screen time for hands-on work. We dive into the challenges he faced, his motivation for making the leap, and how he worked through imposter syndrome and childhood trauma. We’ll also talk about staying true to your values, facing fears of failure, and finding real fulfillment by following your passion.

Episode Takeaways

Making a career flip involves personal growth and self-discovery.
Following one's values and passions is essential for finding fulfillment in a career.
Imposter syndrome and fear of failure can be overcome by taking action and seeking support.
Embracing creativity and pursuing new interests can lead to personal and professional growth.

Connect with Jeff

LinkedIn: https://www.linkedin.com/in/jeffrey-watkin-220aa8196/

Instagram: https://www.instagram.com/countryliving_catalunya

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:

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

🎵 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? 💫

From marketing director to owner of Sun Divers, Roatan, meet Natalie Shuman

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 19 Sep 2024 07:00:00 +0000

Ever wondered what it’s like to swap a high-pressure corporate job for running a dive shop on a remote island?

Natalie Shuman’s journey takes us from the hustle world of marketing to the clear blue waters of Roatan. She opens up about the pressures, recognition, and burnout from her previous career, and how she and her husband followed their dream to own a dive shop. Discover how taking smart risks, setting boundaries, and pursuing passion led her to a fulfilling new life that blends diving with conservation. Dive into her inspiring story and see how she turned her dream into reality!

Episode Takeaways

Flipping your career takes guts and a knack for smart risks.
Setting boundaries is key to keeping your work-life balance in check and avoiding burnout.
Chasing a career that matches your passions can lead to real joy and fulfillment.
Mixing your work with a bigger purpose, like conservation, makes it feel less like work and more like a meaningful adventure.

Connect with Natalie

Get some virtual vitamin C, follow Sun Divers Roatan on Instagram: https://www.instagram.com/sundiversroatan/
Go scuba diving in Roatan: https://sundiversroatan.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:

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

🎵 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? 💫

SAT tutor to the creator of Murdle, meet G.T. Karber

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 12 Sep 2024 07:00:00 +0000

Ever wondered how to take your scattered creative ideas and turn them into a focused, intentional career? G.T. Karber has cracked the code! From juggling various creative projects to becoming a successful mystery writer and creator of the Murdle, an award winning mystery puzzle book series, G.T. shares his journey of honing in on a niche. He talks about the power of intentional branding and rebranding, connecting with a specific audience, and the importance of feedback from those who resonate with your work. Greg also highlights how crafting a public persona and using professional visuals can make your transformation feel real. His key message? Seize the opportunities for change and make intentional choices to reshape your life!

Episode Takeaways

Hone in on a niche and rebrand yourself to align with a specific audience
Create a persona and use photographs to combat imposter syndrome
Be intentional with feedback and seek input from those who align with your niche

Connect with G.T. Karber

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:

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

🎵 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? 💫

SEO specialist to surf-inspired artist, meet Ethan Orenstein

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 5 Sep 2024 07:00:00 +0000

Have you ever been stuck in traffic on your long commute home, wondering if there's more to life than this?

In this episode, Ethan Orenstein takes us through his incredible journey from journalism to content writing, SEO, and digital marketing. Along the way, he discovered his passion for surfboard design and art, which led him to create Wave Arcade, a business selling bamboo surfboard fins. Despite setbacks like the COVID-19 pandemic and algorithm changes, Ethan adapted by refocusing on his art, producing stunning surf and coastal-inspired artwork. He emphasizes the importance of seeing failure and setbacks as chances for growth and reinvention.

Episode Takeaways

Career paths are not always linear, and it's okay to make multiple transitions and evolutions.
Failure and setbacks are valuable learning experiences that can lead to growth and adaptation.
Finding a balance between passion, freedom, and financial stability is crucial in creating a fulfilling career.
Embracing creativity and exploring different interests can lead to unexpected opportunities.
Creating your own path and following your passions can bring a sense of fulfillment and purpose.

Connect with Ethan

Listeners can use code: FLIPPER for 15% off an order on both wavearcade.com & https://wavearcadeart.etsy.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:

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

🎵 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? 💫

Museum curator to teacher, meet Kimberly Masiello

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 29 Aug 2024 07:00:00 +0000

Imagine going to school for your dream career, only to have a friend's dinner conversation open your eyes to a new path you never considered. Suddenly, you want to shift your whole journey!

In this episode, meet Kimberly Masiello, a career flipper who’s transitioned from studying art history and curating museum exhibits to teaching, becoming a principal, and now virtually teaching ESL with her own small business.

In this episode, you’ll hear how Kimberly emphasizes the power of listening and problem-solving. She discusses the importance of creating stability through remote work, which also offers the flexibility to travel and explore new opportunities.

Episode Takeaways

Embrace career changes and create your own path
Remote work provides flexibility and the ability to travel
Listening and problem-solving through listening can lead to success
Create stability for yourself through remote work

Connect with Kim

Kim’s LinkedIn: https://www.linkedin.com/in/kimberly-masiello/

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:

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

🎵 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? 💫

Comedian to keynote speaker on digital balance, meet Jeff Wozer

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 22 Aug 2024 07:00:00 +0000

Ever wondered what it takes to leap from one career to another, chasing dreams and overcoming doubts along the way? Meet Jeff Wozer!

Jeff's career flip story starts with a dream of being a hockey play-by-play announcer, pivots into stand-up comedy, and then transitions into a fulfilling career as a speaker. In this episode, Jeff opens up about the challenges he faced and the doubts that tried to hold him back, all while emphasizing the power of believing in yourself and following your true passion.

Jeff’s insights will inspire you to embrace discomfort, take that leap, and move confidently towards your dreams. Don’t miss this inspiring conversation!

Episode Takeaways

Believe in yourself and have faith in your abilities when making a career change.
Embrace discomfort and vulnerability as part of the learning process.
Connect the dots in your life and trust that everything will work out.
Follow your true passion and purpose, even if others doubt you.
Making a career flip can lead to personal growth, confidence, and fulfillment.

Connect with Jeff Wozer

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:

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

🎵 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? 💫

From MiLB pitcher to country hip hop recording artist, meet Zach Dando

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 20 Aug 2024 07:00:00 +0000

Ever wondered what it’s like to pursue your childhood dream of becoming an MiLB pitcher for the Houston Astros, only to find that it's just one chapter in a much grander story?

In this episode, Zach Dando from Denver, Colorado, shares his incredible career journey, spanning from the excitement of professional baseball to coaching 350 games, turning pro in golf, ranching, and now creating music that’s garnered over 500k streams on Spotify. Zach opens up about the highs and lows of each transition, the challenges he’s faced, and the valuable lessons he’s learned. He highlights the importance of seeking support from those closest to him, particularly his beautiful wife Gabi, and the profound fulfillment he finds in helping others and making a positive impact. Join me to discover how perseverance, self-reflection, and a strong support network have shaped Zach’s career.

Episode Takeaways

Career paths can have twists and turns, and it's important to be open to new opportunities.
Relying on others and asking for help can lead to growth and success.
Finding fulfillment in helping others and being a positive influence is rewarding.
Ego can hinder progress, and being vulnerable is necessary for personal and professional growth. Seeking help and collaboration is important for personal and professional growth.
Putting in the work and staying committed to one's goals is crucial, even in the face of challenges and self-doubt.
Building relationships and a supportive community can have a significant impact on one's journey.
Transitioning into a new industry requires adaptability and a willingness to learn.
Perseverance and self-reflection are key to overcoming obstacles and achieving success.

Connect with Zach

Zach’s Instagram: https://www.instagram.com/dando.music
Spotify Dando.
https://open.spotify.com/artist/2YcttOdNKO07btoI1ueKWx?si=FloY7ISLSJmNH2GQ8F0Ahw

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:

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

🎵 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? 💫

From hospitality manager to content manager/writer, meet Tracy Carmen Watkin

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 15 Aug 2024 07:00:00 +0000

Ever wondered how far a career flip could take you?

Tracy Carmen Watkin shares her journey from hospitality to managing office buildings to moving to Europe and becoming a writer and content manager. Join us as she discusses overcoming imposter syndrome and navigating job searches, all while pursuing her passion for personal training and planning a travel curation business.

Tracy recounts her journey from managing office buildings to relocating to Europe and embracing writing. She opens up about battling imposter syndrome during her career transitions and navigating the challenges of job hunting after a layoff. Tracy also reveals her passion for personal training and discusses her plans for co-launching a travel curation business. Throughout the conversation, Tracy and Jenny underscore the value of ongoing learning and the pivotal role of support networks in pursuing entrepreneurial ventures and side projects.

Episode Takeaways

Career flips can lead to new opportunities and personal growth.
Dealing with imposter syndrome is common and requires self-talk and confidence-building.
Continuous learning is important for personal and professional development.
Having support and partnerships can make pursuing side projects easier.
Exploring different interests and passions can lead to fulfilling and diverse careers.

Connect with Tracy Carmen Watkin

LinkedIn: https://www.linkedin.com/in/tracy-carmen-watkin-8090611a/
Her personal Instagram: https://www.instagram.com/tracywatkin/

Fitness in Context Project

Main website: https://www.fitnessincontext.com/
Instagram: https://www.instagram.com/fitnessincontext/

Travel Curation Project

https://www.instagram.com/escapadeworldtravel/

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:

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

🎵 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? 💫

From sea turtle biologist to vintage reseller, meet Jeremy Smith

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 8 Aug 2024 07:00:00 +0000

Have you ever wondered how your childhood passions could shape your career? In this episode, Jeremy Smith shares his incredible journey from sea turtle marine biologist to vintage picker and reseller.

In this episode, you'll discover how growing up in a family that renovated old farmhouses and loved antiques gave Jeremy an eye for potential. Learn how a chance connection with his high school art teacher led him to sea turtle research. Hear how Jeremy found fulfillment by following his passions and creating his own unique career path.

Key Takeaways

You can pick your own destiny and do whatever you want, but it requires taking the first risk.
Following your passions and interests can lead to unexpected and fulfilling career paths.
Family influences and childhood experiences can shape your career choices.
Embracing opportunities and being open to new experiences can lead to personal and professional growth.
Overcoming imposter syndrome and societal expectations is key to pursuing a non-traditional career path.

Connect with Jeremy

@vintajer on Instagram
Shop Jeremy's furniture at Kurtz Street Marketplace

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:

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

🎵 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? 💫

From professional musician to IT CEO, meet Roy Atkinson

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 1 Aug 2024 07:00:00 +0000

Ever wondered how a full-time musician found harmony in the world of IT? Roy Atkinson's journey from music to tech is a symphony of adaptation and opportunity.

The Career Flipper podcast, hosted by Jenny Dempsey, explores the inspiring stories of individuals who've navigated unique and often unexpected career transformations. New episodes drop every Thursday—don't miss out!

In this episode, Roy discusses his passion for music, transition into tech, and the challenges he navigated. He emphasizes adaptability, the role of technology in his career shift, and the support of community.

Key Talking Points

Embrace change and be open to new opportunities
Adaptability is key in navigating career transitions
Technology can have a significant impact on career changes
Community and support are crucial during times of change
Follow your own unique path and don't be swayed by others' opinions

Connect with Roy Atkinson

Featured Music Credits

All songs from the studio album "Beginnings and Ends" by Roy Atkinson, released by Fox Records:

The Painter’s Eye:

Acoustic guitar, percussion toys, and vocals by Roy Atkinson
Electric guitar by Jack Riley
Bass by Joe Lomoriello
Drums by Christian Starpoli

Pay the Bill in the Morning:

All guitars and vocals by Roy Atkinson

Explore Roy's music and connect with him to discover more about his career journey and current projects.

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:

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

🎵 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? 💫

From nurse to furniture flipper, meet Caitlin Lynch

jenny@jennydempsey.com (Jenny Dempsey) — Tue, 30 Jul 2024 07:00:00 +0000

Ever wondered how a nurse turned furniture flipper navigates career changes and family life while covered in paint and sawdust from a project?

Caitlin Lynch shares her journey from nursing to furniture flipping, emphasizing the importance of personal growth and mindset. She discusses leveraging social media for business growth, balancing career transitions with family life, and the supportive community of furniture flippers.

Episode Takeaways

Personal growth and stepping outside your comfort zone are crucial in career transitions.
Social media can transform a hobby into a thriving business.
Balancing career and family requires dedication to personal goals.
The furniture flipping community offers invaluable support and learning opportunities.
Pursuing passion-driven careers can bring fulfillment despite challenges.

Connect with Caitlin

Connect with Caitlin on Instagram: @caitsflipsandfinds
Follow her on Facebook: Cait’s Creations

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:

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

🎵 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? 💫

From event marketing manager to career coach, meet Karli Williamson

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 25 Jul 2024 07:00:00 +0000

Ever felt like your job defines your entire identity?

Karli Williamson, former Event Marketing Manager and Consultant turned Career Coach, founder of Guided Coaching Co and Lumpy Pot Co.

Karli Williamson’s career journey began in event marketing within the tech industry, where she thrived until burnout and declining mental health forced her to take a leave of absence. This pivotal moment led her to discover her true passions and values, prompting a career shift into coaching.

Episode Takeaways

The impact of burnout and declining mental health in the tech industry.
Challenges of identity tied to work and the importance of finding personal values.
The gradual shift into a new career path and the role of coaching in supporting this transition.

Connect with Karli Williamson

Connect with Karli on LinkedIn.
Schedule a coaching session with Karli at Guided Coaching Co.
- Use code FLIPPERPOD for 25% off a Career Clarity Course.
Order super cute ceramics from Lumpy Pot Co here.

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:

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

🎵 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? 💫

From brain injury therapist to marketing agency CEO, meet Sally Mildren

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 18 Jul 2024 07:00:00 +0000

Ever thought about what making and selling granola can teach you about running a marketing agency?

In this episode, Sally Mildren takes us on her journey from being a burnt-out brain injury therapist to becoming the CEO of her own marketing and customer experience agency—with all the crazy twists and turns in between. She talks about the tough stuff, like dealing with a controlling boss and getting laid off multiple times. Sally dives into why taking risks and chasing your dreams, no matter your age and even when you're scared, is so important. She also shares tips on nurturing your creativity and not waiting for 'someday' to live your best life. Tune in to hear Sally's real-life advice on bouncing back from failures and finding your true path.

Episode Takeaways

Don't be afraid to make career flips and take risks, as they can lead to personal growth and new opportunities.
When facing fear and self-doubt, review the evidence of your past successes and prove to yourself that you have what it takes to make your current endeavor work.
Be intentional about nurturing your creativity and making time for activities that keep your talents alive.
Play out the 'what if' scenarios and realize that the consequences are rarely as tragic as feared.
Embrace messy action and learn from both successes and failures to make improvements and adjustments along the way.

Connect With Sally

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:

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

🎵 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? 💫

From SEO expert to animal communicator, meet Nick Musica

jenny@jennydempsey.com (Jenny Dempsey) — Thu, 11 Jul 2024 07:00:00 +0000

WELCOME TO THE FIRST EPISODE!

Ever wondered what happens when SEO expertise meets animal psychic abilities? Get ready for an eye-opening journey as Nick Musica shares his transition from corporate SEO to animal communication on the debut episode of The Career Flipper podcast!

In our very first episode, host Jenny Dempsey chats with Nick Musica about his journey from corporate SEO specialist to animal communicator. Nick opens up about the challenges he faced and the pivotal moments that pushed him to pursue his passion for animal communication.

Key Talking Points

How intuition and personal growth played crucial roles in Nick's career transition.
The importance of balancing corporate responsibilities with personal fulfillment for overall well-being.
Embracing unexpected opportunities and personal growth through pursuing passions.

Connect with Nick

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:

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

🎵 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? 💫

The Career Flipper Podcast Trailer

jenny@jennydempsey.com (Jenny Dempsey) — Wed, 22 May 2024 19:42:00 +0000

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:

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

🎵 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? 💫