Do What You Want!

Ep 14: How to Know It’s Time To Leave Teaching (with Lisa Harding)


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What happens when you go from CEO of an ed-tech company to a stay-at-home mom to launching a business that helps teachers leave the classroom? Lisa Harding joins Rachael to talk about her unexpected leap into entrepreneurship—and how she went from supporting teachers inside the system to empowering them to find freedom outside of it.

In this conversation, Lisa shares how she overcame the fear of judgment, the ethical questions she wrestled with, and why she felt morally obligated to help teachers transition out of the classroom with support, strategy, and a whole lot of heart.

We also dive into:

  • What sparked Lisa’s career shift (hint: it wasn’t about being her own boss—at first)

  • The imposter syndrome she faced, even after leading a company as CEO

  • Why teachers make incredible employees and entrepreneurs

  • The surprising power of supportive community during any big life transition

  • Her advice for teachers who are scared to make the jump—or unsure if they even should

Whether you’re a burned-out teacher, a quiet entrepreneur, or someone wondering what else is out there—this one’s for you.

🔗 Resources Mentioned:

  • Teacher Career Transition Academy


  • Free Career Directory with 200+ career options for former teachers: Grab it here.

  • Facebook Group for Career Transitioning Teachers: Check it out here


🧠 Connect with Lisa Harding:

  • Instagram: @teachercareertransitionacademy

  • Podcast: Beyond the Classroom


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Do What You Want!By Rachael Johnson