The Lonely Entrepreneur

I've been a business owner for 25 years. If there's one thing I wish I had done differently, I would have surrounded myself with other entrepreneurs much earlier.

People I could be honest with. People who understood the pressure. People I could call when I needed a real conversation.

Because entrepreneurship can be lonely. And I don't think we talk about that enough.

We share the finished projects, celebrate the milestones, and talk about growth. But there's another side that rarely makes it into the conversation.

The uncertainty. The decisions you keep turning over in your head. The responsibility of knowing other people depend on you.

You can spend your entire day surrounded by people and still feel alone.

Who do you talk to when you're the owner?

Your team comes to you for answers. Your clients expect you to deliver. Your family wants time with you, and you want to be present with them.

Meanwhile, who do you talk to about what's actually happening in your business?

Who do you tell when cash flow is tight? Who do you call when a project is going sideways? Where do you take the question you feel like you should already know the answer to?

Sometimes you keep it to yourself, get up the next morning, and carry on.

When you own a business, you get used to figuring things out. But handling everything yourself can become a habit. Eventually, you stop considering that someone else might be able to help.

Looking back, I wish I had understood sooner that being responsible for my business didn't mean I had to work through every challenge alone.

We keep our cards close

I see this especially in construction.

We're guarded. We hold our cards tight to our chest. Another subcontractor can feel like competition before we've even had a conversation with them.

So we keep things surface level.

"Busy?"
"Yeah, slammed."
"Business good?"
"Can't complain."

Sometimes business really is good. Sometimes "busy" means your team is stretched, your margins are thin, and you're waiting on payments you needed last month.

From the outside, those situations can look exactly the same.

Sometimes we're protecting our reputation. Sometimes we don't want to look like we're struggling. Sometimes we've never had a place where it felt okay to tell the whole truth.

Then we compare everything we know about our own business to the small part of someone else's business they're willing to show us.

And we wonder why everyone else seems to have it figured out.

What we miss when we stay guarded

There are subcontractors who have already worked through the problem you're dealing with today.

They've made the hiring mistake. They've learned why a project lost money. They've improved how they estimate, lead their teams, or choose contractors to work with.

You have experience that could help them, too. But none of it gets shared if every conversation stays at "business is good."

Trust takes time, and healthy boundaries matter. Still, there's room between telling everyone everything and telling nobody anything.

There's room to say, "I'm having a hard time with this. How have you handled it?"

To celebrate a win without feeling like you're bragging. To talk about a loss without feeling like you've damaged your reputation.

Those conversations can help us make better decisions and feel less alone while we're making them.

The community I want to build

This is why I want to create a community of subcontractors.

People who want alignment. People who care about how they run their businesses, treat their teams, and support each other.

A safe group where you can show up honestly.

You can share a win and have people celebrate with you. You can talk about a mistake and work through what to do next. You can ask a question without worrying that somebody will use it against you.

We'd talk about what works and what doesn't. Hiring. Estimating. Sales. Leadership. The real challenges of running a business.

And the support would go both ways. Some weeks, you might need help. Other weeks, your experience might be exactly what another owner needs.

Building that takes trust, respect, and people willing to participate. But I believe it's worth doing.

Start before you need the support

If I could go back, I'd build those relationships while business was going well. I'd ask better questions and be more honest with my answers.

You can start small, too. Reach out to another owner you respect. Have a conversation that goes deeper than how busy you are.

After 25 years in business, I know there will always be difficult decisions and seasons that test you. I also believe the journey can look different when you have people beside you who understand it.

That's the community I want to create.

If you're a subcontractor who wants to be part of that conversation, reach out. I'd love to hear what would make a community valuable to you.

No one builds alone.