Welcome to the first episode of Season 2 of The Career Flipper Podcast! Host Jenny Dempsey kicks things off with career flipper Matthew Smith.Matthew went from working in corporate advertising in New York City to bartending in the Caribbean. Yep, you read that right! After losing his job right before COVID, struggling to find a new one, and going through a tough breakup, Matthew ended up moving back home and living in his parents’ basement. But then, a “temporary” job in St. John, U.S. Virgin Islands, came up to help cover his NYC rent. Well, four years later, he’s still in the Caribbean, finding happiness and community he never expected.In this episode, Matthew shares how he made that huge leap, what it was like to leave the city life behind, and how he found a community that helped him grow. He talks about the challenges, the surprises, and why taking risks—despite the fear—can lead to some pretty amazing opportunities.Takeaways:Life either throws you a curveball, or you make a decision to change.Big challenges can lead to big opportunities.Matthew realized he was becoming a version of himself he hadn’t seen in a long time.Happiness matters more than just making money.Give yourself some grace—things don’t always need to be perfect.Losing his job turned out to be a blessing in disguise.It’s okay not to have everything figured out—sometimes you just have to go for it.A strong community can really help you grow and keep you going.Think about what you loved as a kid to help find your passion.Connect with MatthewInstagram: https://www.instagram.com/matthewhs7 This episode is all about taking a leap, embracing change, and finding unexpected happiness. It’s a great listen if you’re thinking about making your own career flip or just need a bit of inspiration to get started. Grab a drink, get comfy, and enjoy!
Thanks for tuning in to The Career Flipper!If this episode made you think, laugh, or feel a little braver about your own flip, do me a favor:💌 Share it with a friend⭐ Subscribe or follow wherever you listen💬 Leave a quick review! It helps other career flippers find our little corner of the internet. Let’s stay connected: 📲 Instagram: @thecareerflipperpod for all things podcast💼 LinkedIn: The Career Flipper Podcast🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper Submit your story:Have a career flip story? Whether you’re in the messy middle or celebrating the other side, I’d love to hear it and maybe even feature you on the show. Submit your story here: thecareerflipper.com. Want to support the show or work together? Book me to speak about career change at your next event, collaborate through sponsorships or affiliates or got another idea? Drop me a note at [email protected] Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses. 🎵 Music Credits Season 1: Intro & outro music by Audionautix.comSeason 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio And hey, remember my favorite question: What’s the best that could happen? 💫

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