Have I Actually Built a Business That Lets Me Work Anywhere?

It's mid-January in Toronto. The snow won't stop.

I just moved into a house, which means I'm now responsible for clearing the driveway. Every few days, same routine.

I'm spending more time indoors than I'd like.

Going to the gym is fine — it's a 5-minute drive. But I miss running outside.

I miss walking to places. I miss not checking the weather app before leaving the house.

This winter is making me ask a question I should have asked earlier: Have I actually built a business that lets me work anywhere I want?

The Honest Answer (Until Recently)

No. I hadn't.

On paper, I ran an "online business." In reality, I was tethered.

SimpleDirect Financing — my first business — served US contractors. That meant US hours. Calls would come in whenever customers felt like calling.

For years, I had a partnership manager who let anyone reach him at any hour. That culture spread. When he left, the calls came to me.

I wrote about this last week — how I finally made the whole thing free and self-serve. That decision was about peace. But it was also about mobility. I just didn't fully articulate it at the time.

The Test I Failed

Last September, I was in Nice. Visiting Monaco for a few days. Should have been a clean trip.

Instead, I was on my phone constantly.

Calls from homeowners. Calls from salespeople. Calls from people who had no business calling me directly but did anyway because that's how the system worked.

I remember thinking: I built this business for freedom. Why do I feel trapped?

The trip before that — same thing. Different city, same problem.

That's when I knew something had to change. Not the business model. The entire design of how I work.

What "Work From Anywhere" Actually Requires

Most founders say they can work from anywhere. Few actually can.

Here's what I've learned it requires:

No synchronous dependencies

If your business needs you on calls during specific hours, you're not mobile — you're just remote.

There's a difference. Remote means you can work from a different office. Mobile means the timezone doesn't matter.

No single point of failure that's you

If customers escalate to you, if decisions bottleneck through you, if your presence is required for things to function — you're not free.

You're just the most important employee.

Revenue that doesn't need babysitting

Client work is fine, but if your income stops when you stop, that's a job with extra steps.

The things that compound — content, equity, products that run themselves — those travel with you.

I didn't have all three. Now I do.

What Changed

This year, I made a few moves:

• Turned SimpleDirect Financing into a free, self-serve product. No more calls. No more account managers. It runs or it doesn't.
• Shifted focus to Founder Reality — content, products, and services that don't require me to be in a specific timezone.
• Changed how I work with consulting clients. Still work with founders, but async by default. Calls when necessary, not when convenient for them.

None of this was one decision. It was a series of small kills and small builds over the past year.

But the result is real: for the first time, my business is only constrained by geography when I choose it to be.

Where I'm Looking

I've been thinking about this more concretely.

Mexico City.

Two-hour timezone difference from Toronto. Dense, cheap, interesting. Good for a month or two without disrupting anything.

Florida.

No visa complexity, same timezone, US banking access. Boring, but boring is fine when you're trying to work, not vacation.

Lisbon.

Five hours ahead, but async-friendly. Gets me European access if I ever want to build relationships there.

The Gulf — Dubai, Abu Dhabi.

I have been a few times. Would go back each year probably.

The point isn't that I'm moving. The point is that I could. That's the difference between freedom and the illusion of freedom.

30-Year Thinking

I'm 28. If I'm lucky, I have 50+ winters ahead of me.

How many do I want to spend shoveling snow and staying indoors for four months?

How many do I want to spend in a city I chose when I was 22 and just never questioned?

Toronto is great. I'm not leaving permanently.

But I want the option to leave temporarily — every year if I want.

That requires building differently. It requires asking, with every business decision: does this add to my optionality or subtract from it?

Most decisions subtract. Most revenue comes with strings. Most growth comes with obligations.

I spent six years learning that the hard way. Now I'm building around it.

The Question

If you're a founder, here's the test:

Could you leave for three months and have everything still work?

Not "could you check in from the beach for an hour a day" — that's not freedom, that's remote work with a view.

I mean actually leave. Different timezone. Sporadic availability. Would your business survive? Would it grow?

If the answer is no, you haven't built a business. You've built a job that owns you.

I spent six years building something that owned me. This year, I finally stopped.