What I Learned in 5 Years of Building My Own Business

Five years. 

In some ways it feels like Gray Breakthroughs has been part of my life forever, but there are times when I can't quite believe it's already been five years. 

And when I think about what has made these last five years possible, I don't think about the projects we've completed or the programs we've created — I think about the people. The clients. The colleagues. The collaborators. One of the great joys of the past five years has been watching this evolve from something I built into something we are building. 

So, thank you for trusting me, for challenging me, for opening doors, and for allowing me to do work that I genuinely love. 

Along the way, I knew I would learn a lot from being my own boss, but I never anticipated these lessons… 

You Don't Have to Know Where to Start 

I learned that clarity doesn't always come before action. Sometimes action is what creates clarity.  

Part of success is failure. And part of failure is trying. When you don’t have all of the information — because sometimes you can’t — just trying something will provide clarity.  It can reveal the pros and cons, the strengths and weaknesses that no decision-making framework ever could. 

If you had asked me five years ago exactly what Gray Breakthroughs would look like today, I wouldn't have been able to tell you. And I'm increasingly convinced that's the point. 

Your Best Ideas May Already Exist 

Pay attention to the things you do subconsciously. For a long time, there were things I simply did. I knew how to walk into a room, listen to what was happening beneath the surface, ask the right questions, and help people find a way forward. 

Overtime, I have learned to identify those instincts; to name them, to teach, repeat and improve them to the point where they are no longer just innate to me, but rather a replicable framework for how we work at Gray Breakthroughs. 

Don't Let What You Started Become the Ceiling 

I started Gray Breakthroughs based on what I knew then. 

But I'm not the same leader I was five years ago. My vision today is bigger. It includes new ways of helping leaders and organizations. It includes possibilities I haven't even imagined yet. 

And maybe that's the biggest lesson of all. To honor what you built. Be grateful for what got you here. But don't become so attached to the original vision that you miss the opportunity to build the next one. 

The Journey Shapes the Destination 

There are always going to be things outside your control. How you navigate them as a leader is what makes the real difference. Staying curious. Staying adaptable. And remembering who helped get you there along the way. Because you’re not building a business in a bubble; you’re building something that will be influenced by the world around it. 

If you want to keep up with what’s influencing my business decisions, join my newsletter, The Gray Matter.