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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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Fehlende Folgen?
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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!
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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 pathRemote work provides flexibility and the ability to travelListening and problem-solving through listening can lead to successCreate stability for yourself through remote workConnect with Kim
Kim’s LinkedIn: https://www.linkedin.com/in/kimberly-masiello/
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 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 WebsiteJeff's LinkedInThanks 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 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.musicSpotify Dando.
https://open.spotify.com/artist/2YcttOdNKO07btoI1ueKWx?si=FloY7ISLSJmNH2GQ8F0AhwThanks 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 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 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 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 InstagramShop Jeremy's furniture at Kurtz Street MarketplaceThanks 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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