I joined Entrepreneurs’ Organization (EO) Cleveland in June of 2020, smack in the middle of the pandemic. The world was unraveling, and I was navigating a minefield of business uncertainty, personal fear, and a future I couldn’t predict. I didn’t go looking for EO. A friend mentioned it offhandedly, and something just clicked. It felt like I’d stumbled onto a room where I didn’t need to translate. For the first time, I was around people who spoke entrepreneur.
And if you’re an entrepreneur, you know what I mean.
Your team assumes you’re rich. Your friends think you’ve got it made. Your family wonders why you’d ever take these kinds of risks. And somewhere underneath all of it, you’re carrying the fears, the what-ifs, and the responsibility of keeping it all together. Being a business owner can be profoundly lonely-even when you’re surrounded by people.
Joining EO didn’t erase that. But it changed how I carried it.
The Power of Finding ‘Your People’
One of the most impactful parts of Entrepreneurs’ Organization is something called Forum.
It’s a small, curated group of 7–10 business owners who meet monthly in a confidential setting. I was lucky to find a Forum where I fit. It wasn’t just industry diversity-it was a mix of ages, backgrounds, experiences, and perspectives. Some were further along in their business journey; others were figuring things out in real time, like me.
But the magic wasn’t in their resumes. It was in their mindset. These were people who took their growth seriously. People who made space for real conversations, not just surface-level wins.
Shifting from Control to Leadership
As a business owner, I like structure. I like process, metrics, clarity. Our team runs EOS (Entrepreneurial Operating System), and I’m proud of how far we’ve come. But I used to equate leadership with oversight-checking in, staying close to the details, making sure nothing fell through the cracks.
What I saw in EO members was a different kind of leadership. People who empowered their teams to solve problems, own outcomes, and grow through accountability. Not abandonment. Not passivity. True ownership.
That challenged me. Still does.
But it helped me see that sometimes the best way to lead is to step back, not lean in. To let others rise. To allow space for bigger thinking, not just more doing.
Letting Go of the Guilt
Maybe the biggest shift came from something simple: seeing how other Entrepreneurs’ Organization members prioritized rest, travel, and family without guilt.
I’m the white-collar sheep of a blue-collar family. My parents were hardworking, humble people. I inherited their work ethic-and their deep, unspoken guilt about not working.
So when I met EO members taking three-week trips or stepping away from their companies without panic, I thought, “How? How can you do that and not feel like you’re falling behind?”
Now, as I write this, I’ve just returned from my first-ever extended trip to Italy with my wife. It’s not that EO gave me permission. It just helped me realize I didn’t need to ask for it.
I’ve come to see that the real damage to a business isn’t from stepping away. It’s from never stepping back to think. To rest. To breathe. Some of my best ideas come from space. And EO helped me see that space is a strategy, not a weakness.
The Vulnerability Effect
If there’s one thing that surprised me most, it’s this: vulnerability is a superpower.
In Forum, we practice something called the 5% Reflection. You spend most of your life sharing the 95% you want people to see. In Forum, you share the 5% you usually hide: the fears, doubts, frustrations, and personal realities that don’t make it onto your LinkedIn profile.
You talk about your marriage. Your health. Your doubts as a parent. Your burnout. The decision you’re afraid to make. The client you just lost. The money you can’t figure out. And in return, you don’t get advice-you get shared experiences. Someone saying, “Yeah, I went through something like that. Here’s what happened.”
No fixing. No preaching. Just real connection from people who get it.
Growing by Giving
A year ago, I became the Chair of EO Cleveland’s Mentorship Program. I’d never had a formal mentor until then. Now I have one, and I also mentor others. And let me tell you: nothing has accelerated my learning like teaching and being taught in equal measure.
Mentorship inside EO isn’t transactional. It’s not, “Let me tell you how to do this.” It’s, “Here’s how I handled something similar. Take what you need.”
Through mentorship and Key Leadership programs, I’ve watched myself and my team level up. We’ve reinforced what we’re already good at, and we’ve gotten honest about what we still need to build.
The Real Takeaway
Look, I’m not trying to sell you on EO. This isn’t a pitch.
But if you’re a business owner, I will say this: find your tribe. Find the group of people who understand what it’s like to carry the pressure, the vision, the fear, and the hope of running a company.
Find the group where you can say the quiet part out loud.
The right peer group won’t tell you what to do. They’ll help you hear yourself. They’ll reflect back the best of you when you forget it. And they’ll walk beside you when the road feels long, uphill, and lonely.
At Sanctuary, our tagline is Partners in Growth. That means our clients, our team, and our community. But it has to start with us. We can’t help others grow if we’re stuck in place. And growth doesn’t happen in a vacuum.
Whether it’s EO or something else, don’t go it alone.
Because yes, the journey is yours.