I heard a phrase this morning that carries a lot of weight in my house:
“You know what, Dylan? I’ve been thinking. I think you’re right.”
This time, it was Lisa — starting to see the perspective I’ve been trying to communicate for months. The one where I uproot how we’ve done life for years and create something new: six months in the U.S., 90 days in Spain, 90 days in Canada. Not running away — just reaching for more.
We talked. A real talk. About the reality of being an entrepreneur — about how different the world looks when you're the one carrying the payroll, worrying at 2 AM, building something from nothing. About how those conversations are rare. We looked at our circle and realized that very few people are thinking this way — and they all happen to be other entrepreneurs.
It's Not About the Math Anymore
This week, I ran the numbers. Tax implications between Texas, Calgary, and Spain. Personal income, corporate income — all of it. The truth? It’s all relatively the same. So the decision to go isn’t about money anymore.
What it is about — is purpose, freedom, and the diminishing return on effort.
As a business owner, you eventually hit a wall. No matter how hard you work, the output stops increasing. You start wondering: “If I just keep grinding this out, will it ever feel worth it again?” And when the answer starts leaning toward no, you begin asking a new set of questions.
Conversations That Hit Different
I had coffee with a friend this morning — a fellow entrepreneur with branch offices, capital at risk, and the weight of it all on his shoulders. He said something that stuck:
“You don’t own the business. The bank does. But at least you don’t have a boss.”
That’s the kind of grim, funny truth only another founder can appreciate.
He sees a recession coming. He’s younger, has a different risk profile, but the principle is the same: how much is enough, and what’s the payoff for taking the next leap?
Another friend runs a $40 million concrete business. Three partners. Two have checked out, and he’s holding the whole thing up. He told me:
“At the end of the year, after everything, we might split a couple million — but I’ve got hundreds of staff, bank covenants, jobsite fatalities, liability. It’s exhausting. Honestly, I’d make more net if I just ran a small concrete crew and went home at 5.”
That one hit. Because it echoes a universal entrepreneurial truth: once your basic needs are met, why keep building unless it really matters?
I’ve Asked This Question Before
Back in my 30s, I went through a crisis of purpose. I asked some of the wealthiest Calgarians I was managing money for two questions:
- If you’ve made $100K, how do you make $1M? If $1M, how do you make $10M?
- Why do you keep doing what you’re doing?
The answers?
- To the first: “I’m working on it.”
- To the second: “Because it’s all I know.”
At 30, that shook me. I didn’t want to build a future where the only reason I kept going was because I didn’t know what else to do.
Today, nearly 20 years later, I’m not in a crisis. I’m in a recalibration.
I’m asking: What’s the highest and best use of me — of my energy, my resources, and my time?
And more importantly: Is this still the place I want to burn that energy?
Labor Costs and Market Pressure
Later today I spoke with one of our site supervisors — a great guy who’s helping scale our Latino crews. We talked wages. Entry-level general laborers in Calgary now start around $25/hour, and skilled site supervisors can approach $35–$40 with bonuses.
And they’re earning it. The cost of living is rising, and labor is getting more expensive. But companies are stuck. Prices haven’t caught up to wage increases yet, so businesses are eating the difference. For now.
It’s a dangerous place to be — especially in a tight-margin business. Most small businesses don’t have cushion. Most are run month-to-month, year-to-year. So if costs go up but pricing doesn’t, the collapse won’t be dramatic — it’ll just be quiet.
The last ones standing will be the ones with enough endurance to carry the loss until the market finally adjusts.
And I’m asking myself: Do I want to be one of those last ones standing?
The New Realization
First, I thought moving might be a tax advantage. Turns out it’s not.
Then I thought it might be a quality-of-life advantage. Maybe. But I need to dig deeper into the cost of living in places like Texas vs. Calgary.
What I do know is this: I want to work in a place that still believes in working.
A place where energy and ambition aren’t seen as suspicious — they’re fuel.
So as I look at where to build next — U.S., Spain, or stay here — the math says stay. But the gut says go. And lately, I’ve learned to trust my gut more than my spreadsheets.
So, Is Today a Stay or Go Day?
Today?
It’s a go day.
Not because I have to go. But because I can go. Because the freedom I’ve earned should give me the permission to ask better questions — and chase better answers.
And if you're an entrepreneur reading this, you know exactly what I mean.
Watch on YouTube