The Ladder Has No Top

I’m sitting in a poorly lit office waiting for an accountant.

The carpet is that grey-brown colour that exists only in professional offices and airport hotels. There’s a framed degree on the wall that nobody has ever looked at twice. I’m 26. I’ve just started a sock company, and I’m trying to understand the tax implications of what is, at this point, essentially a lemonade stand.

He explains that in Canada, if you make over $30,000 in four consecutive quarters, you’re obligated to collect and remit GST.

I laughed out loud.

“There is no fucking way we’re making thirty thousand dollars selling socks.”

And I meant it. We had a few hundred bucks in revenue. We were selling socks hand to hand at university like we were running a street hustle.

I was a former cyclist. The pay in professional cycling was somewhere between dismal and non-existent. I didn’t come from money. Thirty thousand might as well have been thirty million. The number was abstract. Foreign. A figure that happened to other people.

We did $350,000 that year. Selling socks.

That was my first lesson in the smallness of my own thinking.

Fast forward about a year.

I’m in a slightly better lit office, this time waiting for a lawyer. My cofounder has walked away. An early partner is making it impossible for me to run the business. I need help finding a path forward. A way to regain control of something that felt like an extension of myself.

I lay out the whole story. The partnership, the falling out, the mess.

Then I drop what I think is the headline:

“And we’ve done over a million dollars in revenue this year.”

I say it the way you’d play an ace. Like that number alone should communicate everything about what’s at stake.

He barely blinks.

“Oh, that’s all? Why don’t you just walk away and start over?”

I remember staring at him thinking, Did I stutter? A MILLION dollars.

More money than I’d ever imagined touching. More than anyone in my family had made in a year. And this guy is waving it off like a rounding error.

But there are levels to this game.

And the people who’ve been playing longer can see things you can’t. That lawyer wasn’t dismissing me. He was showing me, without meaning to, that I was still thinking small. That my ceiling was somebody else’s floor.

These two moments cracked something open in me.

Until then, I’d been operating inside constraints shaped entirely by my past. By what I’d seen, what I’d known, what felt plausible based on where I’d come from.

And look, I was confident. Delusionally so. I believed I could build something great. But those dreams had ceilings. Invisible ones. Like I’d imposed a limit for no reason I could name.

Maybe it was protection. Maybe it was some quiet part of me that didn’t feel worthy of more.

That accountant’s office and that lawyer’s office were my shattering moments.

After them, I stopped thinking in ceilings.

Here’s the part nobody tells you about what happens next.

You climb.

You climb past every number you once thought was impossible. First six figures. Then seven. Then eight. A five-figure hour. A six-figure day. Milestones that your former self would have framed and hung on a wall.

And each one, in the moment, feels... cool for a minute. Then flat.

The champagne pops. You check the dashboard one more time. You tell a few people. And by Tuesday it’s just the new normal.

I used to think something was wrong with me. That I was broken in some entrepreneurial way. That I’d become the person who couldn’t enjoy what they’d built.

But I’ve since learned this is the condition. It’s not a bug. It’s the operating system.

Entrepreneurs recalibrate. We reach a milestone, absorb it into our new baseline, and immediately look upward. The number that would have made 26 year old me weep with joy barely registers at 35. Not because it isn’t significant. But because the frame has shifted. Again.

Entrepreneurship is climbing an infinite ladder.

You keep going. Rung after rung. And it never quite feels like you’ve arrived, because each step feels a lot like the last one. The view barely changes. The air doesn’t get easier to breathe. You just look up and see more ladder.

The problem is, you rarely look down.

My friend Andrew Wilkinson built a company worth over a billion dollars by 36. And he described hitting each new financial milestone the same way I’d describe mine at a fraction of that scale.

The amount doesn’t matter. The feeling is identical. That first hit of excitement. The rapid normalization. The immediate hunger for the next rung. He called himself an addict, unable to stop swimming forward.

What shook him was meeting people worth ten times, a hundred times what he had, and finding them in the exact same state. Still striving. Still unsatisfied. Still looking up.

It’s never enough. At any level.

I think about this constantly now.

I think about the final episode of The Office, where the series is ending and Andy Bernard says, “I wish there was a way to know you’re in the good old days before you’ve actually left them.”

That line gives me chills every time. Because it’s devastatingly true.

When you ask anyone about their greatest moments, you don’t hear about revenue milestones. You don’t hear about the dashboard or the bank notification or the moment the wire hit.

You hear about the tough times. The near-death experiences that made the company what it is. The 2am calls with your cofounder. The camaraderie of a small team fighting above their weight class. The stupid inside jokes. The moments that, at the time, felt like survival but in hindsight were the peak.

Those are the good old days. And most of us blow right through them reaching for the next rung.

I’m ten years into this now. I’m only starting to learn the lesson.

Not that ambition is bad. Not that milestones don’t matter. Not that you should stop climbing.

But that the climb is the thing. It was always the thing.

The destination is a lie you tell yourself to keep moving. And that’s fine. You need it. But if you sacrifice every present moment for a future arrival that will feel just like today, you’ve missed the entire point.

The 26 year old sitting in that accountant’s office? He was having the time of his life and didn’t know it. Selling socks out of a backpack. Terrified. Excited. Completely alive in a way that no revenue milestone has matched since.

If you’re somewhere on the ladder right now, reading this on your phone between meetings or at the end of a long day, do me a favour.

Stop.
Look down.
See how far you’ve climbed.

Then look around at exactly where you are. The people beside you. The work in front of you. The particular texture of this specific rung.

This is it. Right now. The part you’ll miss later.

Don’t wait for someone to tell you.

You’re in the good old days.