Cocoon Conversations: My Career Flip Progress for May 2025

In this episode of "Cocoon Conversations" on the Career Flipper podcast, I, Jenny Dempsey, take you along on my career journey.  

This year, I’ve committed to opening up about my own career flip, just as I encourage my guests to do. So here we are, in May 2025, and I can hardly believe it’s been four months since I started my current day job. It feels surreal to say that, especially considering I was laid off for two years before this.

During this time, I’ve been balancing my full-time job with furniture restoration on the side, dedicating Sundays to it, and squeezing in podcasting and all the related tasks whenever I can. If that sounds overwhelming, it is! Life can be a juggling act, and I know I’m not alone in feeling this way. Scheduling time with friends often feels like a game of Tetris, as we all navigate our busy lives.

I’ve always been the type of person who thrives on variety. I’m the one multitasking—doing laundry while putting away dishes, preparing to record a podcast, creating social media content for my furniture flipping page, and making sure my dog, Dwight, gets outside for a potty break. My brain has always thrived on this mix of activities, and I’ve been like this for as long as I can remember.

Looking back, I’ve come to realize something significant. For a long time, I believed that work—capital W work—was my identity. I thought it was the only thing I was good at. I didn’t believe in taking vacations; if I did, I’d bring my laptop along and continue working. I even had a panic attack in front of a customer service team I was managing because I was so consumed by my job. I poured everything into my work, only to learn the hard way that companies would replace me in an instant. When I was laid off and struggled to find a new job for two years, I was left questioning my identity. Who was I if I wasn’t working?

I dive into this and more in the episode!

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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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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? 💫