The Coach Who Changed How I Lead | A Tribute to Ola Sage

Everyone needs a coach to help them get where they’re going.

For most of my life, I believed independence was the goal. I took pride in figuring things out on my own, carrying the weight, and pushing through. What I eventually learned is that independence has a ceiling. I wasn’t going to get where I wanted to go by myself. That lesson didn’t come from a book or a spreadsheet. It came from working with the right coach.

Along the way, I worked with an extraordinary one, Ola Sage. It’s an almost comically perfect last name for someone whose gift was helping people see more clearly. Ola was instrumental in my development as a business leader. She led a group she called No Limits, and it wasn’t a slogan or motivational shorthand. It was a challenge to stop shrinking our ambitions to fit inside what felt safe.

For me, “no limits” didn’t mean more revenue or bigger growth charts. Ola helped me get honest about what I actually wanted. I wanted more time at home with my family. I wanted a business that supported my life instead of consuming it. Through that work, I eventually articulated a simple, practical mission: creating Apple Spice fans, daily, not just among customers, but vendors, employees, and everyone who came into contact with the business. Ola had a way of helping you see that culture wasn’t a side project. It was the product. One of the principles that emerged from those conversations was the quiet discipline of under-promising and over-delivering. It wasn’t framed as a tactic, but as a way of respecting people.

We met once a month for 90 minutes, and those sessions never felt transactional. Ola is a pianist, and our conversations always felt like jazz to me. There was deep listening, space between ideas, and a rhythm that allowed clarity to emerge without forcing it. She asked questions that didn’t rush toward answers, but instead helped you hear your own thinking more clearly.

One of the core practices in the group was something we called “processing.” One person would sit in the hot seat while the rest of us asked questions, not to solve the problem, but to understand it. Ola taught us to listen for meaning, not just words. To listen for intent. That distinction changed how I communicate to this day.

She pushed us beyond surface-level business questions and into deeper ones. What’s keeping you up at night about this decision? What are you not saying? What assumptions are you making that might not be true? When you ask questions like that, and when a group knows how to hold space instead of rushing in, you get honest answers. Sometimes surprising. Sometimes uncomfortable. Always useful.

Watching people work through real issues in real time was awe-inspiring. It taught me something Ola understood intuitively. Business is never just dollars and cents. It is people. It is relationships. And those relationships will either sustain a business or quietly undermine it.

When COVID hit, Ola continued to mentor me without charging anything. She said, “If I’m not here for you now, when you need help the most, then what am I doing?” She didn’t just teach accountability. She modeled it. She showed me how to make people feel seen, how to challenge without diminishing, and how to lead without ego.

All of this while also running her own cybersecurity company. Coaching leaders wasn’t her job. It was her calling. A passion project built around walking alongside people as they became better versions of themselves.

Marcus Aurelius begins Meditations with a section devoted entirely to gratitude, naming the people who shaped him. This feels like my version of that practice. I’ve written before about honoring people who mattered deeply to my journey, including this tribute to Frank Losi and about the importance of finding the right guide when learning something new, like I shared in my reflection on learning classical guitar at 48.

This one is for Ola.

I didn’t learn that independence has a ceiling from a book or a spreadsheet. I learned it from working with the right coach.