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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/contactThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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/sdscoopsquadConnect on Facebook: https://www.facebook.com/sdscoopsquadThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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Saknas det avsnitt?
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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/juliermorrisThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 DirectoryWebsite: https://sandiegoartdirectory.com/ Instagram: https://www.instagram.com/sandiegoartdirectory/In the Art Scene PodcastWebsite: https://intheartscene.comInstagram: https://www.instagram.com/in_the_art_scene/ Galina’s ArtworkWebsite: https://galinamarcus.com/ Instagram: https://www.instagram.com/galinamarcus_art/Thanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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!
X: https://x.com/chrishayreInstagram: https://www.instagram.com/chrishayre/Also referenced in the episode, shout out to Ty: https://www.instagram.com/tynowell/
Connect with ChrisThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 fulfilledFeelings of guilt and shame are common when making career changes, but it's important to prioritize your well-beingTaking time off to rest and reflect can help in unraveling your thoughts and making decisionsCourage and creativity are necessary when pursuing unconventional career pathsIt's important to listen to your own desires and not worry too much about what others thinkConnect with Danielle
LinkedIn: https://www.linkedin.com/in/adaniellel/Thanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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/itscatchengIn NY? Order from her drool-worthy bakery: https://www.instagram.com/catsbakesnySee what tasty food she’s enjoying: https://www.instagram.com/catzeatzCheck out her YouTube channel: https://www.youtube.com/channel/UCii1s41Xzf_VadAMTIN6ABQThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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/thejasonscrivenInstagram: https://www.instagram.com/divorce101_LinkedIn: https://www.linkedin.com/in/jasonscriven/Thanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 audienceCreate a persona and use photographs to combat imposter syndromeBe intentional with feedback and seek input from those who align with your nicheConnect with G.T. Karber
Play Murdle onlineOrder your copy of MurdleThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
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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 ArtWave Arcade Etsy StoreWave Arcade InstagramWave Arcade TikTokThanks for tuning in to The Career Flipper podcast!
If you loved this episode, spread the word! Share it with a friend, hit that subscribe button and don’t forget to leave a review—it really helps spread the word to more career flippers like you.
Let’s Connect:
Join the flippin' fam: thecareerflipper.comTikTok: https://www.tiktok.com@thecareerflipperInstagram: http://instagram.com/thecareerflipperpodGot a career flip story? I want to hear all about it & have you on an episode! Whether you’ve flipped or are about to, or right smack in the middle of a flip, drop me a line: [email protected]
Want to support the show? You can hire me to speak at your event about career changes or let's collaborate through affiliates or sponsorships. Interested? Reach out at [email protected]
Take my customer service courses, maybe? Before being laid off, I spent years in customer experience leadership, helping teams improve how they serve their customers. That work didn't stop with my corporate job—it’s now helped over 12,000 students worldwide through the online courses I’ve built. Whether you're looking to switch to customer service or sharpen your skills, these courses are packed with real-world tips, from handling tough conversations to managing customer interactions. Check them out at thecareerflipper.com/courses!
Other ways to get involved with the show:
Buy me a coffeeCheck out my furniture flipsIntro & outro music by audionautix.com!
- Visa fler
