The Courage to Follow the “What If” (Ep 133)

Notes

What happens when you leave a career you love, not because you’re burned out, but because another opportunity keeps whispering, “What if?”

In this Midlife Leap episode, Kathy talks with former middle school teacher Julie Thomas, who spent 16 years teaching seventh-grade English before stepping away from her dream job to explore an unexpected entrepreneurial path.

What began as a side investment in short-term rental properties gradually evolved into a full-scale pivot, complete with the emotional rollercoaster of leaving a beloved career, navigating imposter syndrome, and learning how to build a business from scratch.

Julie shares the realities of solopreneurship: the loneliness of leaving a team environment, the financial uncertainty of building something new, and the constant pressure of being responsible for your own success.

But her story also reveals something powerful about midlife reinvention: sometimes the path forward isn’t the one you planned. Through a series of unexpected conversations and a willingness to stay open to possibility, Julie discovered a completely new business, rooted in something she loved, and maybe for longer than she realized.

In this conversation, Kathy and Julie explore the courage it takes to pivot, how to listen to your intuition, and why trusting that you’ll “figure it out” might be the most important skill of all.

Key Takeaways

Sometimes you leave a career you love not because it’s wrong, but because something new calls to you. Julie wasn’t burned out. She loved teaching and had her dream position. But a growing real estate venture (and a new baby!) forced her to reevaluate how she wanted to spend her time and energy.

Entrepreneurship can be lonelier than people expect. Leaving a highly social profession for solo work brought unexpected emotional challenges. The loss of daily collaboration and feedback can be one of the biggest adjustments when starting a business.

Imposter syndrome often appears when we move outside our formal training. Julie felt confident teaching others about rentals, but running the business itself -marketing, finances, client acquisition – was an entirely new skill set she had to learn in real time.

Midlife reinvention often requires multiple pivots—not just one big leap. Julie’s journey wasn’t a single decision. It included leaving teaching, launching coaching, exploring property management, returning to substitute teaching temporarily, and finally landing in design.

The most powerful mindset shift: trusting that you’ll figure it out. Julie realized that even if a risk didn’t work out, she trusted herself to adapt. That belief made it easier to pursue opportunities that felt both exciting and scary.