She'd been swimming upstream for ten years. Alone.


We rode the elevator from the fourth floor down to the parking garage.

Three of us — riding mostly in silence. Each holding a box with the few contents of our desks from years of building Disney Online together.

The elevator stopped and the doors opened....

We stepped out, gave one another a quietly awkward "well, see you around... maybe" glance, started our cars, and pulled out of the parking lot ... for good.

That's how my career as an entrepreneur began in June 2007, Reader. An exhale carrying equal parts relief, excitement, fear, hope, anxiety, and uncertainty.

Since that elevator ride, I've consulted big and small companies, led a digital media agency, owned a fitness brand, built an annual international cycling event, and established a coaching practice to help passionate business owners build momentum in their life's work.

A day or two after the exhale and the leap, one unsettling realization becomes:

You are on your own.

Business ownership has a powerful way of making people feel alone. Even in partnership. Even with a full team. Even when things are working.

I've felt it. Nineteen years in, I still feel it sometimes.

And it compounds. Loneliness impedes decision making, clouds judgment, lowers creativity. When I coached endurance cyclists, training sessions that went poorly could be directly correlated to self-reported feelings of isolation.

The body keeps score, and so does the business.

We get so acclimated to just handling our shit — to "what happens next is on me" — that we become numb to how normalized alone has gotten. We build entire unintentional structures around it. Finding ways to make ourselves the center of everything.

The consequence is we run like fugitives.

Until something shifts the physics.


I don't tear up easily. But a client texted me this recently.

I didn't know it could feel like this.

At our next session my friend added: "For the first time in ten years, I don't feel like I'm swimming upstream. Alone."

Alone.

That word lingered in the room for a moment.

Upstream I understood. Going from paddling against the current to moving with it. That's something you can feel in your body.

But alone landed differently.

Because what my friend was describing wasn't just a feeling. It was a structure she'd built around herself — carefully, competently, without ever deciding to. Ten years of being the only one who could figure something out before she could hand it off. Ten years of all data flowing in through her, all decisions flowing out through her, her team working hard to make her happy.

The alone wasn't accidental. It was operational. And it looked, from every angle, exactly like good leadership.

I have to figure it out before I can hand it off. I have to be the center. What happens next is on me. This is just how it works.

Ten years of those tiny scripts running through everything. Like subroutines in a computer's operating system. Not because she was doing it wrong. Because nobody had held up a mirror long enough for her to see they were scripts at all.

Those scripts built the structure. And the structure had a cost.


The cost was a team that operated with limited range of motion. Everything ran in and out through her — like the hub and spokes of a wheel. Her team, incredibly talented, had become fixated on trying to impress her. And that kept them small.

It kept her small too. Her creative power got bogged down in the friction of minutiae that could actually make others grow.

What shifted weren't systems. What shifted were the stories — and her trust in herself, and in the people around her.

She started making her actual clients real to her team. Not abstractions. Not metrics. Real people — their stories, their struggles, what her work had actually done for them. She wanted her team to feel the same kinship with the people they were serving that she felt.

Her team stopped trying to impress her and started trying to serve them.

She started asking her team to figure things out rather than waiting until she'd figured them out first. Which meant they could take risks. Make decisions. Grow into their domains. Become more interdependent and less leader-dependent.

The script rewrote itself. From I have to be at the center of everything to I want to be the kind of leader who creates an environment people are excited to build in. Hers was a shift from ME to WE.

She moved from the center of the operation to the center of the mission. Different position entirely.

When an employee left, two others stepped in. Eager. Growing into new territory. Taking risks they wouldn't have taken before.

None of this was about efficiency. It was about what happens when the me story becomes a we story — and the whole business reorganizes around the shift.


A few days later, another text arrived.

I don't feel alone in this anymore.

That's it. That's the whole thing.

Not "I feel better." Not "things are going well." Not "the business is working."

I don't feel alone in this anymore.

Nineteen years of building on my own — and I know exactly what she means. The alone isn't just a feeling. It's a tax. The weight of being the only one who can see the whole picture, make the final call, hold the thread when everything else is fraying.

When that lifts — when the people around you are growing rather than orbiting, when the team is moving toward something they believe in — the physics change.

Not because the problems disappear. The prototypes were still late. The pages were still on the wrong side.

Because you're no longer running that marathon alone.


The scripts running your business right now probably got you here. The self-reliance. The control. The insistence on figuring it out first. Those aren't character flaws. They're survival strategies that solidified into operational structure.

But scripts have a way of outliving their usefulness without announcing it. Some keep us small when we're ready to go bigger. Some keep us hedging when we're ready to commit. Some keep us adding — more projects, more ideas, more tactics — when what we actually need is more clarity.

And most of them are running below the surface. Invisible, load-bearing, and expensive.

As one of my mentors likes to say, “What we aren’t changing, we’re choosing.”

What helps — what my friend discovered, what I keep discovering — is building a trusted support structure that brings a different perspective to what's hiding in plain sight. Not someone to fix what's broken. Someone to see what you can't see from where you're standing.

That's the antidote to the particular loneliness of building something on your own.

So here's where we start. Finish this sentence and hit reply:

"The thing I keep doing alone that I don't have to do alone is ___."

I read every one. Sometimes it turns into a conversation. Sometimes that conversation turns into work we do together — the kind where someone sits in it with you for a stretch and helps you see what you can't from where you're standing.

Either way, you'll have said the thing out loud. That's where it starts.

Running's for fugitives. Remember to exhale.

P.S. Something's brewing for a specific kind of fugitive — the coach or consultant who's good at the work but has never quite figured out how to make people feel why it matters. The kind who feels like an amazingly kept secret. A small group thing, this fall. More soon. If that's you and you're impatient, reply "tell me" and I'll loop you in early.

Running's for Fugitives

Every month, one dispatch. Philosophical, snarky, and occasionally practical. No productivity tips. No growth hacks. No self-help magic. Just an honest look at what keeps most entrepreneurs on the run — and what shifts your physics so you can build something you're actually proud of.

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