Before I joined EO, I thought asking for help was a sign I did not have things figured out.
I was wrong.
I am a member of EO Chicago, the Entrepreneurs’ Organization. I want to write about what that has meant, because I do not think enough business owners know what they are missing.
Running a company is isolating in a way that is hard to explain to people who have not done it. You are responsible for the payroll, the clients, the team, the strategy, sales, and the cash flow, all at once. Your employees look to you for direction. Your friends outside business think you are doing great because you own a company. Nobody in that circle is the right person to hear the real version of what is happening.
That was me before EO.
The Forum is the core of EO membership. A small group of entrepreneurs meets monthly. What happens in that room stays in that room. Members do not give advice. They share their own experience and let you draw your own conclusions. That format changed something in me.
I grew up thinking you worked through your problems privately, figured them out, and then told people the outcome. EO flipped that. You share the problem while you are in it. You say out loud what is actually happening, what you are afraid of, what you do not know. And the people across the table from you have been there. They are not consultants. They are not vendors trying to sell you something. They are owners who have sat in the same seat.
The first time I did that, it was uncomfortable. I am not built for vulnerability by default. But something shifted when I said a real problem out loud and the room did not flinch. Someone said, “I went through something similar.” Someone else asked a question that I had not thought to ask myself. I left that meeting seeing the situation differently.
That became the pattern. Not answers handed to me, but clarity I could not get alone.
EO also pushed me to be better in ways I did not expect. When you are around people who are building serious things and asking hard questions of themselves, you raise your own standard. It is not competitive. It is motivating. You want to show up with something real, and that discipline carries back into the business.
The other thing nobody tells you is that you make real friends. Not networking contacts. Friends who know what is actually going on in your company, who ask follow-up questions the next month, who are rooting for you.
I run CIO Landing, a managed I.T. services company in the Chicago area. The decisions I make as an owner are better because of EO. Not because anyone told me what to do, but because I stopped making them alone.
One member described it this way: having a group of entrepreneurs who want you to succeed, who will listen to your problems, share similar experiences, and make decisions feel less heavy. His only regret was not joining earlier. That tracks with my own experience.
If you own a business and you have never talked to anyone in EO, find a member and ask them about Forum. The worst that happens is you hear a story that sounds like yours.