Description

In this episode, host Jenny Dempsey chats with Annie Cole of Vancouver, WA, a financial coach who’s no stranger to career flipping. Annie shares her journey from social work to education, then ed tech, and finally launching her own business focused on financial coaching for women. Along the way, she’s learned the importance of self-care while making intentional career moves. She offers real, practical advice for anyone considering a career change or starting a business—like utilizing free resources, seeking mentorship, and taking it one step at a time. Annie also highlights how bridge jobs can provide financial security and breathing room while you figure out your next step. Whether you're thinking about flipping your own career or diving into entrepreneurship, this conversation is packed with insights on navigating change without being too hard on yourself.

Key Takeaways:

• Career changes don’t have to be all-or-nothing—you can transition gradually while keeping financial stability.
• Bridge jobs can be a smart way to stay financially secure while exploring your next career move.
• Networking and mentorship can open doors you didn’t even know existed.
• Taking risks (and even making mistakes) is part of the process—what matters is learning and adjusting along the way.
   

Connect with Annie

• Instagram: https://www.instagram.com/build.wealth.with.annie/
• Coaching: https://www.money-essentials.com/
• LinkedIn: https://www.linkedin.com/company/money-essentials-for-women/

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🪑 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? 💫