How do you know when it's time to make a big career change, even if you're not sure what’s next?
In this episode, I’m excited to reconnect with Jake Conneen, who I know from high school in the little Southern California town we grew up in, Norco. Now based in El Paso, Texas, Jake shares his wild ride of career flips—from construction to journalism, restaurant management, the military, nursing, and now running his own woodworking biz, Doby’s Craft House, named after his dog. Jake’s all about taking smart risks and following what truly makes you happy, even if it means flipping careers more than once. He opens up about how the stress shifts when you start working for yourself, and why self-care and time management are a game-changer. And to keep it real about how we juggle all the things, you may also hear his daughter, Rosemary, in the background during the episode! He’s leading by example for her, showing the importance of chasing passions and making her own choices.
If you’ve been thinking about a career flip but aren’t sure how to take the leap, Jake’s story will definitely inspire you!
Episode Takeaways
Connect with Jake
https://www.dobbyscrafthouse.com/
Instgram: https://www.instagram.com/dobbyscrafthouse/
YouTube: https://www.youtube.com/@dobbyscrafthouse
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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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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? 💫
