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:

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, 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:

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 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:

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 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:

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, 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:

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, 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:

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, 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

• The S’mores Cart
• Elyse Events
• Kelley W Photos

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:

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 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:

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 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:

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? 💫

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:

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? 💫