The Career Flipper Podcast

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. Despi...

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 ow...

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...

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 th...

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 jou...

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...

Ever wondered how a full-time musician found harmony in the world of IT? Roy Atkinson's journey from music to tech is a symphony of adaptation and opportunity. The Career Flipper podcast, hosted by Jenny Dempsey, explores the inspiring stories of individuals who've navigated unique and often unexpected career transformations. New episodes drop every Thursday—don't miss out! In this episode, Roy di...

Ever wondered how a nurse turned furniture flipper navigates career changes and family life while covered in paint and sawdust from a project? Caitlin Lynch shares her journey from nursing to furniture flipping, emphasizing the importance of personal growth and mindset. She discusses leveraging social media for business growth, balancing career transitions with family life, and the supportive comm...

Ever felt like your job defines your entire identity? Karli Williamson, former Event Marketing Manager and Consultant turned Career Coach, founder of Guided Coaching Co and Lumpy Pot Co. The Career Flipper podcast, hosted by Jenny Dempsey, explores the inspiring stories of individuals who've navigated unique and often unexpected career transformations. New episodes drop every Thursday—don't miss o...

Ever thought about what making and selling granola can teach you about running a marketing agency?  In this episode, Sally Mildren takes us on her journey from being a burnt-out brain injury therapist to becoming the CEO of her own marketing and customer experience agency—with all the crazy twists and turns in between. She talks about the tough stuff, like dealing with a controlling boss and getti...

WELCOME TO THE FIRST EPISODE! Ever wondered what happens when SEO expertise meets animal psychic abilities? Get ready for an eye-opening journey as Nick Musica shares his transition from corporate SEO to animal communication on the debut episode of The Career Flipper podcast! The Career Flipper podcast, hosted by Jenny Dempsey, explores the inspiring stories of individuals who've navigated unique...

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 podca...