The Career Flipper Podcast
Feeling stuck in your career? There's always a way to flip it!
Welcome to The Career Flipper, hosted by Jenny Dempsey, who is navigating her own career flip. Jenny started this podcast out of curiosity and a desire to learn from others who have successfully transformed their careers. Here, you'll find real-life stories of people who have made remarkable career changes across various industries. Whether they've faced a layoff, started a new business, pursued a side hustle, or taken a completely unconventional path, these journeys showcase how others have successfully carved out their unique career paths.
Jenny's interviews dive deep into the highs and lows of career changes, offering practical advice and plenty of encouragement to help you feel less alone. Discover how to overcome fears, build confidence, and find a career that truly lights you up. Join us and get inspired to flip your own career script!
2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo
From the film industry to professional dog walker, meet Justin Cohen
From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz
From lawyer to therapist and author, meet Lauren Tetenbaum
From product manager at Amazon to startup founder, meet Jane Dashevsky
From psychology PhD to frontend software engineer and career transition coach, meet Manana Jaworska
Laid off? Now what? Finding healing, hope and your next step with Steve Jaffe, Author of The Layo...
From paralegal to dog psychologist and trainer, meet Hilary Pratt
From corporate banking to mother + leadership coach, meet Raina Gandhi
CX Leader & PreK Teacher + Cruise Event Cofounders, meet Wendy and Elizabeth Pochop
From talent acquisition to to Tai Chi instructor, meet Baiba Wisse
From people operations manager to certified executive coach, meet Natalie Robbins
From corporate banking to career transition coach & recruiter, meet Lori Wallace
From donut maker to consumer & CX insights strategist, meet Beth Karawan
A corporate sales and thrifted fashion curator, meet Liz Dekofsky
One year of flipping: Cocoon reflections, career chaos & an original song
Musicologist to strategic communications advisor, meet Lisa Chensvold
From software engineer to customer experience to AI entrepreneur, meet Mariena Quintanilla
Bathroom tile sales to personal brand & marketing manager, meet Joseph Rudd
From US Navy Captain to Professional Photographer, meet Laura Hatcher
From corporate marketing to chateau owner & event curator, meet Trish Jasinski
Cocoon Conversation for June 2025
From software engineer to chocolate maker, meet Case Sandberg
From Guest Experience Manager with Cirque du Soleil to Ghostwriter, meet Carolene Méli
From politics to nonprofits to executive coach, meet Katie O'Malley
From renaissance faire merchant to cartographer, meet Jenna Leveille
Cocoon Conversations: My Career Flip Progress for May 2025
From academia to holistic canine nutrition, meet Alexia Mellor
From psychology to real estate to artist, meet Victoria Tara
From corporate HR to HR consultant, meet Megan Pawlak