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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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

• Play Murdle online
• Order your copy of Murdle

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? 💫

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

• Check out Wave Arcade Art
• Wave Arcade Etsy Store
• Wave Arcade Instagram
• Wave Arcade TikTok

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? 💫

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:

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? 💫

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

• Jeff's Speaking Website
• Jeff's LinkedIn

Thanks for tuning in to The Career Flipper!

If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:

💌 Share it with a friend
⭐ Subscribe or follow wherever you listen
💬 Leave a quick review! It helps other career flippers find our little corner of the internet.

Let’s stay connected:

📲 Instagram: @thecareerflipperpod for all things podcast

💼 LinkedIn: The Career Flipper Podcast

🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper

Submit your story:

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

Want to support the show or work together?

Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com

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

🎵 Music Credits

Season 1: Intro & outro music by Audionautix.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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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

• Roy's LinkedIn
• Clifton Butterfield, Roy's IT consulting company

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:

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? 💫

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:

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? 💫

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:

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? 💫

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.

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!

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:

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? 💫

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

• Sally Mildren’s LinkedIn Profile
• Boss Lady Consulting Website

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? 💫

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!

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 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

• Book an animal psychic reading session
• Book an intuition reading 
• Follow Nick on Instagram

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? 💫

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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 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? 💫

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 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? 💫

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:

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? 💫

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:

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? 💫

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:

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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫

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 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? 💫