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May 29, 2025 43 mins

In this episode of The Career Flipper, I chat with Jenna Leveille, who went from working as a merchant in the travelling Renaissance Festival circuit to becoming the Deputy State Cartographer of Arizona and now she’s the VP of State and Local Government Strategy at a mapping company. 

But this journey? It’s anything but straight. Jenna’s path weaves through non-traditional college years, a detour into zoology (because saving the world felt like a good place to start), and finally landing in the world of geospatial tech and GIS.

We talk about what it’s like to not have it all figured out, to follow your curiosity, and to keep showing up, even when the next step is unclear. If you’ve ever felt like your career map is a bit...hand-drawn in pencil, this one’s for you. Jenna proves you can absolutely make your own route—and that community, resilience, and a little self-trust can take you further than you imagined.

Connect with Jenna

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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 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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