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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

In this episode of "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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

What happens when 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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

Today’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.

• 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

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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

In this episode of The Career Flipper, 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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

In this episode of "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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

In 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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

In this episode of The Career Flipper 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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫

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:

Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected]

Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫