Entrepreneur Spotlight 96: Jadine Cleary

Q: Let’s take it back to the beginning: Can you tell us the story of your business’s first month?

A: My first month in business did not start the way I’d envisioned! I wanted to feel aligned, energized, and excited—but instead, I felt resentful. Certain things in my life weren’t aligning, pulling me away from my vision of ease and leaving me feeling behind.

I had planned to launch on April 1, but I pushed it to April 15. At first, that felt like failure. But then I realized—the deadline was mine to begin with. Funny how we high performers set rigid expectations for ourselves, isn’t it?

And yet, I’m so glad I launched when I did. It was my first lesson in starting before you feel ready. Stepping forward even when things don’t feel perfectly aligned. I put my brand out there, embraced the discomfort of being seen and critiqued—and the response was incredible. People loved the company and were excited to see me step into my new role.

My biggest takeaway? Stop navel-gazing. Look up. Step forward. Progress doesn’t come from waiting. It comes from moving.

Q: Was there a time when a person or experience changed your life and your perspective on it?

A: Yes, my first mentor. She taught me the greatest lesson I ever learned about influence, and it had nothing to do with leading others—but everything to do with leading myself.

Years ago, I had the chance to sit down with a two-time Olympic gold medal coach—someone who had shaped world-class athletes. I was thrilled. I had my plans laid out, eager to share how I was going to develop my team, elevate their performance, and help them win.

I was ready to impress her with my strategy. But then she stopped me, looked me right in the eye, and asked: ‘What makes you believe you are the person to lead them to gold?’

I was stunned. I had focused so much on how I would influence them… but I hadn’t once asked myself who I needed to be to create results in them.

That single question shifted everything for me. I realized that influence isn’t about what you do to others—it starts with WHO YOU ARE. The best leaders don’t just develop others; they develop themselves first. Because people don’t follow titles or plans. They follow confidence, clarity, and conviction.

This is now at the core of how I teach leaders to elevate. Influence isn’t about control, persuasion, or telling people what to do. It’s about the presence you bring, the trust you build, and the example you set. It’s important to learn how to cultivate that kind of influence—so that when it’s time to lead, people don’t just listen… they believe.

Q: What is your biggest challenge right now, and what drives you to keep going?

A: My biggest challenge right now is the very thing that fuels me—my boundless excitement for transformation. I say yes to too many things because I see the potential in every leader I work with. I thrive on helping people unlock their next level, but scaling a business requires discipline in where I focus my energy.

What drives me to keep going? The moments when a leader truly steps into their own influence. When they shift from doubting themselves to owning the room. When they realize they don’t have to force impact—they are the impact. That’s what keeps me pushing forward, growing my company, and bringing in other coaches who share this mission.

Scaling isn’t just about growing revenue—it’s about expanding the reach of transformation. And that’s a challenge worth embracing.

Bonus: Have you recently achieved an accomplishment or been featured in an article that we can celebrate with a shoutout?

A: Additionally, I’d love to share my love and profound gratitude to have Libby as a friend.

Libby is the big sister every entrepreneur needs—the one who sees your potential before you do. She brings unwavering wisdom, unstoppable strength, and a vision that lights the path for others. She won’t just support you; she’ll love you into recognizing your worth and give you the strategies to turn your ambition into your vision of success.

She is the godsend to entrepreneurship.