I just wrapped up my Saturday morning run — a rhythm I’ve come to enjoy for clearing my head. Saturdays will be my wrap-up days. A weekly debrief to put a bow on the thoughts, decisions, and realizations that surfaced.
This week was full.
We had an election.
I started publicly sharing my thoughts about leaving Canada.
And I realized it’s not about the taxes. It never was.
What I Thought Was a Money Decision Isn’t
My original plan was to spend half the year in the U.S. on a visitor visa, 90 days in Spain as I’ve done in past years, and the remainder in Canada. I assumed this desire stemmed from a tax advantage or financial leverage — but after running the numbers, I now know that’s not it.
The math is mostly neutral.
What it is about is this: watching something that was once great become less great.
The city I’m in. The province. The country. All of it growing in the wrong directions — not necessarily bigger or better, just heavier, more complicated, less hopeful.
That realization has opened up a whole new thread in my thinking:
If it’s not about money, then what’s the real reason to go?
The Start of Something New
I've started outlining a path to apply for an E-2 visa to move to the U.S. and build a business there. It requires at least $100,000 in investment and a solid business plan. I’m leaning toward Austin, Texas. Not because I plan to open a brick-and-mortar company, but because my startup may thrive in a more ambitious ecosystem.
May Austin has a culture. A pulse. Momentum.
And I want to see if I can match it.
Meanwhile, Back in Calgary
We’ve got enough booked work this year to double the size of our business. That alone brings a new set of responsibilities. I’m not a field operator, but I am the owner — and that means I’m responsible for the people. So we’re growing the team, including adding someone local to handle purchasing, invoicing, and boots-on-the-ground tasks our overseas support can’t manage.
We’re scaling the project management side as well. I even dusted off my old copy of The E-Myth — because when you double in size, you can’t just ask everyone to work harder. You need structure, systems, and the right people doing the right things — without the owner micromanaging everything to death.
Conversations with Fellow Founders
This week I talked to a friend who thinks a recession is coming in Canada. He’s building his business as if one’s already started. He’s frustrated — mostly because he doesn’t yet have the operating “hacks” that let a business thrive in hard times. That tension reminded me of something I learned taking over my current business during COVID:
“If you can only run your business when times are good, you don’t really know how to run a business.”
During COVID, we hacked our way to profitability. Now that we’re in a growth phase, we need a whole different set of hacks. Each season of business requires its own playbook.
Stability Is a Myth — But That’s Okay
One theme kept coming up this week: stability vs. instability.
We are not guaranteed anything — not in life, not in marriage, not in business. And yet, as business owners, we carry the responsibility of providing stability for our teams even when the environment is anything but stable.
That’s the job. That’s the burden. That’s the call.
The political chaos — whether it’s in the U.S. or here in Canada — isn’t new. It just feels new because we had a couple decades of calm. But the truth is, we’ve always been building on sand. And that’s why I’ve adopted the only sustainable posture I know:
Play the ball where it lies.
Don’t pretend the terrain is different. Don’t wish for better conditions. Just play the game that’s actually happening — not the one you wish was happening.
So… Am I Still Going?
Yes.
I’m still working toward going. I’m going to keep chasing the idea of the American dream — not because it’s easy, not because it’s perfect, but because I still believe there are places where ambition is rewarded, where hope isn’t ridiculed, and where building something still matters.
I’ll keep vlogging and blogging this journey.
But if you asked me today — stay or go?
It’s 100% still a go day.
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