One of the hardest things for my founder clients to do, at least as we start working together, is take a break.

My clients have teams. They have people who can, for some period of time, run the company without the founder.

And yet, at least at first, the founder resists this idea.

“I want them to know I’m there for them.”

What they won’t say out loud:

I need them to need me.

No. You need them NOT to need you.

Your company isn’t worth anything until it doesn’t need you.

Until you can go away, for a month, or a year, and come back to everything as good or better than it was before.

We’re in the middle of the summer. Some founders proudly say they are taking time off, while staring at their phones in the middle of family outings and muttering things like “this will only take a second.”

Don’t get confused between what your business needs and what you need.

Take the time off.

The Fourth of July is a great time to test this out.

See who needs who.

Does the business need you, or do you need the business?

Is your business really a business if it can’t survive without you?

It took two heart attacks before Mike would consider that the problem might be him.

He runs one of the most successful construction companies on the West Coast. Strong, tattooed, always in motion. The guy who solves everything.

That was the problem.

Because he solved everything, his people brought him everything. He’d replace their good ideas with his better ones, then wonder why they stopped thinking. He’d trained them to need him — and then resented that they did.

He grew up in a neighborhood full of crime and drugs, and learned to control everything around him to stay safe. That control built his company. Now giving it up terrified him.

It was the one thing he needed to do.

I invited him to Denver for two unstructured days. No agenda. He kept asking for one. I kept shrugging.

People expect me to push, to fix, to hand them a tool. I don’t. Mostly I get quiet. And I wait.

We didn’t talk about strategy or solutions. We just stopped rushing. And in the quiet, what was in the way stopped hiding.

It was him.

I didn’t tell him that. I didn’t have to. Sure, I might have poked and prodded a bit. But mostly I stayed quiet long enough for him to see it himself — the thing that had been true the whole time.

And then he began to see other possibilities.

Leaving the office for a month. New locations without living on the road. Actually being in a conversation with his wife instead of somewhere else in his head.

A bigger company. And less work.

He left lighter. Happier.

And fidgeting just a little bit less.

Sometimes what you most need to see only shows up the moment you stop looking for it.

Only one thing. You.

I was having coffee with a friend, a nonprofit executive director who felt stuck.

He came to me with a list of things that he wants to do—adding programs, adding locations, increasing the impact of the incredible work that he has been doing with youth in our valley.

I asked him what was the first thing he needed to do.

“I need to raise enough money to add some paid positions.”

I live near Aspen. It’s a fascinating combination of people who struggle with the insanely high cost of living, and a small number of people who have multigenerational wealth.

The small number of truly wealthy people support a lot of good causes.

My friend has one of those causes. People love him and the work that he does. But he has always had trouble raising enough money.

“I have some issues with money,” he confided.

Tell me more.

“There is so much money in this valley that I think, at a certain level, it’s vulgar.”

I looked at him.

“So you think money is vulgar. Do you wonder why you have trouble raising it?”

Oh. He laughed. And then I saw his eyes well up. This wasn’t about him. He was just the messenger for a bigger mission. And his beliefs—that he was an artist, that he should struggle, that the people who had money were bad and greedy and even vulgar—were getting in the way of him fulfilling that mission.

Hundreds of kids in our valley are counting on him to let go of all that.

What Would Be Fun?

There’s usually a way around your rules. A fun way to get to the same place.

“I’m not very good at asking people for money.”

“What if you didn’t have to?”

This week my friend is reaching out to parents whose kids have gone through his programs. He has worked with some of them for several years. I asked him to collect stories. To ask how his work with them has impacted both the child and the parents.

“You don’t think some of those people are going to ask how they can help you? Or offer to introduce you to other people who want to help you?”

His eyes welled up again. “That’s a conversation I would love to have.”

Do the thing you love doing. Everything flows from that.

The Cage You Have Built

Every person I have worked with has had at least one major “rule” that they thought was true but was really just made up. And when we identified it and let go of it, everything changed.

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A client told me Thursday that once he has $2 million in passive income, he will feel free.

When he came to me a few months ago, he was working on doing less in his business. Letting his team lead.

He occasionally would let himself do these things. Let things be easier.

Then he would instinctively go back to working hard at creating the freedom he said he needed. Setting his goal at $2 million.

I asked him about his week so far.

He had hired an assistant. He brought on a consultant to help his sales team.

These are things that used to take months (hiring the assistant already had). But in the last week something had shifted. He was making decisions without overanalyzing them.

He also left the office early a couple days, going out to play golf, or going home and working on projects and enjoying the weather. Getting away from the grind of the office. Puttering, even.

He used the word “lighter.” He said he was enjoying himself. He was smiling.

“That sounds a lot like freedom,” I said.

This is the trap. We pick a number — a revenue milestone, a net worth threshold, a business valuation — and tell ourselves that’s when we get to feel free. That’s when we stop grinding. That’s when life begins.

We convince ourselves that freedom is on the other side of suffering.

But freedom isn’t at the end of a number. It’s a way of being. And my client was already living it.

The $2 million isn’t wrong as a goal. But making it a prerequisite for feeling free? That’s worth examining.

Because here’s what I’ve seen after a decade of working with founders and other high achievers: the people who feel free after hitting the big goal are usually the ones who were building the internal conditions for it all along.

The ones who don’t? They might get to their number. But when they get there, they think they must need a bigger number.

Freedom isn’t waiting on the other side of an achievement. It’s available right now. The fastest path to it is noticing you might already have it.

Want To Go Deeper?

You might wonder how my client was able to let go—or how you can. To get more details on the what and the how, subscribe to my weekly email list—

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