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Why It’s Okay to Walk Away From Something That’s “Working”

It’s December 2022 in Andermatt, Switzerland.

I’m sitting in the lounge at The Chedi Hotel with friends…low lighting, soft leather chairs, that quiet, expensive calm you only find in places where no one is trying to impress anyone else.

Across from me is an old friend. A trusted business friend from London. We worked together in real estate development back in 2005. He’s done very well for himself since. His company has built most of Andermatt into what is now a quiet, if-you-know-you-know ski destination in the Alps, anchored by the five-star resort we’re sitting in.

At some point between sips of a drink, I tell him I’m stepping away from my business. Possibly selling it.

He looks at me and asks the most reasonable question in the world:

“Is it cash flowing?”

“Yes,” I say. “It’s e-commerce. It’s basically an unlimited ATM.”

He doesn’t hesitate.

“Then why would you get rid of it?”

I pause. Shrug. Take another sip.

“I want to do something else.”

It didn’t sound like a good enough answer. And at the time, I didn’t have a better one.

But hindsight is 20/20. And if I could answer him now, I’d say this:

I had already done it.

It started as proof of concept and turned into a cult brand. One I was the face of. One where too much hinged on my presence, my energy, my constant involvement.

It wasn’t a laundromat. I couldn’t just show up once a month and collect the winnings.

Even transitioning from CEO to Chairman would required me—my time, my identity, my emotional labor. And I didn’t want to do that anymore.

What I really meant that night was:

It was time to move on to work that didn’t feel so hard.

It was time to get out of the weeds.

It was time to bet on myself again.

There’s a huge misconception in American culture that if you quit something, you’ve failed.

That you didn’t fight hard enough.

That you weren’t worthy.

That you gave up.

But sometimes quitting isn’t failure. Sometimes it’s discernment.

I was at a point where I wanted to leave behind good enough in search of something better. Something that brought me more fulfillment. More joy. More alignment.

And let me be very clear about this:

Leaving something that is objectively successful, something that is working, profitable, admired, and stable takes an enormous amount of bravery.

Especially when you’ve poured your blood, sweat, and tears into building it.

I wasn’t running from something.

I was betting on myself.

I was betting on the belief that there was something out there that was better for me.

And the real question I had to answer was this:

Would holding on jeopardize my long-term happiness, fulfillment, and joy?

For ten years, I lived a great life.

No money stress.

Stability.

Freedom, on paper.

But for me… it was just good enough.

So why did that one conversation, fireside at The Chedi, make me hesitate?

Why did that one question—why would you get rid of it?—make me scared to do a clean exit?

Instead of divesting in one decisive move, I held on.

I took a sabbatical.

I turned off the engine one valve at a time.

I told myself I was resting. Recovering. Catching my breath after an incredible ten-year run.

But the truth is, I was putting my dreams on the back burner.

A small part of me thought I’d just fire up the old website, dust off the balloon printer, and start again.

But that ignored the reason good enough was no longer enough.

2026 is the year I stopped putting my own desires on hold.

My true passion is community.

It’s helping others.

It’s building things that don’t require founders to sacrifice themselves at the altar of their business.

That’s why I launched ONT.

We’re not an agency.

We’re not idea sellers.

We’re an embedded e-commerce business partner.

We give founders agency.

We help people who are stuck in growth put systems in place so their business doesn’t keep them hostage the way mine did.

Because here’s the uncomfortable truth I learned too late:

If you’re thinking about an exit after year five, you’re already behind.

Systems take time.

They need to be built early.

They need to become second nature.

When my business started growing fast, our systems were built for a small to mid-size company, not a company about to 6x its revenue.

So I panic-hired.

I spent a lot of money trying to fill the gaps growth had opened.

People were happy to step in, do busy work, and collect a paycheck.

But what I actually needed was structure.

Clear pillars.

Teams with real ownership.

By the time I figured that out, we were in year seven.

Too late? Or just late?

That question is exactly why I do what I do now.

I embed myself in growing companies to help founders build the teams and systems that allow their e-commerce businesses to print money without constant oversight.

So, should I have sold my business when I had the chance?

Yes.

Should I have had a better answer that night at The Chedi?

Probably.

But I didn’t have it figured out yet.

And I was alone on Founder Island…which, if you’ve been there, you know can be a very lonely place.

If you’re reading this and you feel stuck in the weeds…

If your business is “working” but costing you more than you’re willing to admit…

If you’re carrying it instead of leading it…

You don’t have to do it alone.

If you want to talk, schedule a call with me.

Let’s see if my curated team of senior operators can help you build something that works for you—not the other way around.

Sometimes walking away isn’t quitting.

Sometimes it’s choosing yourself.

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