Thinking about making a career change but have no idea where to start? You’re not alone.
Welcome to The Career Flipper, the podcast for anyone wondering, "What else is out there?". I’m Jenny Dempsey—your host and a fellow career flipper. I didn’t plan on changing careers, but after years in customer experience and a surprise layoff, I found myself asking, "How do people actually make big career moves? And more importantly, how do they keep going when it gets messy, overwhelming, and scary?"
That curiosity led me to just ask people who have done it. To have real, honest conversations with people from all over the world who’ve made all kinds of career flips. Whether they started over in a new industry, turned a side hustle into a full-time gig, or made a total 180 to do something they actually love, their stories gave me ideas, inspiration, and even a little courage - so I figured they might give that to you too.
Be sure to subscribe on your favorite podcast platform for new episodes every Thursday.
Got your own flip story? I’d love to hear it! Submit your story for a future episode at https://www.thecareerflipper.com
Follow on Instagram: @thecareerflipperpod
You don’t have to have it all figured out. Just take that first step. What's the best that could happen?
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From high school English teacher to owner of E-WRITE, writing training consultancy, meet Leslie O’Flahavan
Épisode 29
mardi 10 décembre 2024 • Durée 28:45
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.
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.
🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
Submit your story:
Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com.
Want to support the show or work together?
Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at hello@thecareerflipper.com
Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.
🎵 Music Credits
Season 1: Intro & outro music by Audionautix.com
Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio
And hey, remember my favorite question: What’s the best that could happen? 💫
From perinatal genetics counselor to SaaS customer experience manager, meet Lauren Rose Eimers
Épisode 28
jeudi 5 décembre 2024 • Durée 36:05
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.
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.
From corporate head of sales & marketing to startup founder, meet Tushar Jain
Épisode 20
mardi 29 octobre 2024 • Durée 32:06
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.
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.
From baker & pastry chef to global CX leader, meet Luke Jamieson
Épisode 19
jeudi 24 octobre 2024 • Durée 29:57
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.
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.
From behind the corporate desk to out in the field as a CBS LA Sports Anchor, meet Chris Hayre
Épisode 18
mardi 22 octobre 2024 • Durée 40:02
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!
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.
From geographer to public speaker & trainer, meet Frank Winters
Épisode 17
jeudi 17 octobre 2024 • Durée 42:19
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.
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.
From VP of Sales in manufacturing to workplace trauma coach, meet Rob Connelly
Épisode 16
jeudi 10 octobre 2024 • Durée 34:36
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.
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.
From nutritionist to software developer, meet Danielle Lewis
mardi 8 octobre 2024 • Durée 34:21
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
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:
From real estate & law enforcement to founding Cucina di Pizza, meet husband and wife team, Ashley & Tony Ross
Épisode 15
jeudi 3 octobre 2024 • Durée 31:05
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.
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.
If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:
🪑 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? 💫
🪑 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? 💫
🪑 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? 💫
🪑 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? 💫
🪑 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? 💫
🪑 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? 💫
🪑 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.
🪑 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? 💫
💌 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.
🪑 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? 💫
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