In this episode of "Cocoon Conversations," host Jenny Dempsey gets real about the emotional rollercoaster of juggling her career and furniture-flipping side hustle. She spills on burnout, imposter syndrome, and the chaos of pricing her art (“Am I worth it?!”). Jenny shares her messy, vulnerable moments—singing to her furniture, doubting herself, and still showing up. She reminds us that spirals aren’t failures, but part of the process, and that confidence is more like a flickering patio light than a spotlight. It’s raw, relatable, and a little unhinged—in the best way.
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🪑 And if you want to see my career flip furniture flips in real life, follow me at @sandiegofurnitureflipper
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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.
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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 hello@thecareerflipper.com
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.com
Season 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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