Educational Leader to Entrepreneur

Educational Leader to Entrepreneur

April 01, 20254 min read

From Educator to Entrepreneur – A Journey of Nurturing, Training, and Transformation
- Part 1

Where It All Began

I grew up in a home where leadership was part of everyday life. My parents were both involved in leading churches, and from an early age, I saw what it meant to guide and support a community. It wasn’t about standing at the front—it was about serving others with care, consistency, and purpose.

As a teenager, I began leading Sunday school classes and youth groups. These early experiences gave me a natural sense of responsibility and a growing desire to help others grow. Looking back, those moments planted the first seeds of what would become a lifelong passion for mentoring, teaching, and leadership.


A Life Devoted to Education

Over the next 12 years, I poured myself into education. I completed four degrees, began a PhD, and moved through various leadership roles—from middle management to 2IC at one of Sydney’s leading schools.

What kept me grounded wasn’t the career progression—it was the people. Whether it was helping a student find their confidence, supporting a colleague through a tough season, or contributing to a team culture that valued growth, I found deep satisfaction in making a difference.


The Shift I Didn't Expect

After years of working toward a very clear goal—becoming a principal—something unexpected happened.

It was just after COVID, as schools began to reopen, that I noticed a shift in myself. My wife and I had planned a trip to Europe, and as we travelled, I began reflecting on what life outside of the school system could look like. The structure I had always relied on didn’t feel quite right anymore.

I didn’t leave education because I was burnt out—I left because something new was calling. Even though I had imagined staying in schools long-term, I felt ready to explore a different kind of impact.


Starting Over, Learning Again

Launching a business while overseas came with plenty of challenges. I had to build new systems, find support, and develop skills I’d never needed before—like marketing, sales, and automation.

But what helped me most was recognising that I didn’t have to do it alone. I invested in coaching and joined communities where I could learn from others. That decision made all the difference. Not only did it fast-track my progress, it reignited the same passion for growth and learning I’d always had as a teacher.


Paying It Forward

As I found my footing, I naturally began helping others do the same. I shared what I’d learned with new business owners—people who were where I’d been just months before. Sometimes it was practical support, like how to set up a lead magnet or run a workshop. Other times it was simply offering encouragement and clarity in a confusing moment.

In many ways, I had returned to my roots—not in a classroom, but still teaching, still guiding, still helping people move forward with confidence.


What I Now Know for Sure

1. Invest in Yourself
Your growth as a leader begins the moment you choose to keep learning—even when it’s uncomfortable.

2. Step Into the Unknown
Uncertainty is part of every transition. It’s also where the biggest breakthroughs happen.

3. Share What You’ve Learned
If you’ve gained insights that helped you grow, don’t keep them to yourself. Someone else needs that wisdom too.

4. Build Strong Connections
The journey is always easier—and more enjoyable—when you’re surrounded by others who understand the road you’re on.


Moving Forward

Today, I bring together everything I’ve learned as an educator and entrepreneur to support others on their own journey. Whether you're building a business, leading a team, or simply figuring out your next step—know that growth takes time, but it’s always worth it.

Your story matters.
Your experience has value.
And your next chapter could be the one that changes everything.


Your Turn: Reflect and Reset

If you're at a turning point or simply feeling the pull toward something more, take five minutes and ask yourself:

  • What have I outgrown—but haven’t let go of yet?

  • Where do I feel most alive, even if it doesn’t “make sense” right now?

  • Who could I learn from, or support, in the next stage of my journey?

Write down your answers. Don't overthink it. Often, clarity comes not from waiting—but from movement.


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James and Jennifer

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