I turned off Stripe auto-renewals last Thursday.

SimpleDirect Financing. My first real business. Built it in college when I didn't know what I was doing.

Ran it for five years. Taught me more about grit than anything else in my life.

Now it's free. Forever.

I emailed every customer myself. No more billing. No more account managers. No more phone support. The platform runs, you use it, nobody pays.

Zero replies.

Five years. Thousands of customers. Not one person cared enough to respond.

That told me everything.

September 2025. Nice, France. Day trip to Monaco.

I'm supposed to be having one of those moments. The Mediterranean. The yachts. The "I built this" feeling.

Instead I'm standing outside a café at 5 am taking a call from a homeowner in Texas who's angry about her financing application.

Our partnership manager - he guy I paid specifically to handle this - had stopped working. Not quit. Just... stopped. Still took the paycheck. Told customers to "go find George."

So they found me. All week.

At dinner. Walking through old town. Before the sun came up. Didn't matter what time it was in France - someone in Texas had a problem and my number.

This wasn't new. Same thing happened the trip before. And the one before that.

I landed back in Toronto and fired him the same day.

Firing him was easy. Fixing what he broke took months.

He'd trained everyone to call me directly. Problem? Call George. Question? Call George. Confused? George.

I had to retrain an entire customer base to use support tickets like normal humans. Some adapted. Most just stopped calling, which was fine.

But somewhere in that process I started asking a different question.

Not "is this profitable?" It was.

Not "does this work?" It did.

Do I want this?

The answer was no. Had been no for a while. I just didn't want to admit it.

I don't want strangers calling me at 5am. I don't want to be the single point of failure for a business I stopped caring about. I don't want my mornings ruined by someone else's emergency about a product I built when I was 22.

I want to disappear for a month and have nothing break.

SimpleDirect couldn't give me that. So I killed it.

Here's what I sent:

No apology. No "we regret to inform you."

Just: here's what changed, here's what you save, thanks.

I expected pushback. Got silence.

Turns out nobody cared about the thing I'd spent five years building.

They just wanted it to work. Now it works and it's free. Everyone wins. I win most.

It's Tuesday afternoon. I'm on my couch. Snow outside. Toronto winter. Brutal.

One month ago this scene would've felt like a cage. Stuck inside. Can't run outside. Gym's fine but I miss movement, walks, sun.

Now I'm looking at the snow and thinking: I could be in Mexico City on Friday.

Not "someday." Friday. Book it tonight. Leave Thursday.

Lisbon. Florida. Anywhere with wifi and no winter.

Not because I'm retired. Because nothing I do now requires me to be anywhere specific, at any specific time, answering to anyone specific.

No timezone stress. No "what if someone calls."

No rogue employees blowing up my phone while I'm trying to look at the Mediterranean.

This is what I was building toward for years. I just didn't realize how much of my own structure was blocking it.

I traded MRR for peace.

Traded nostalgia for mobility.

Traded being needed for being optional.

That last one is hard for founders. We're wired to feel important. Indispensable. "The business needs me."

No it doesn't. And if it does, you built a job, not a business.

I built a job five years ago. Last Thursday I quit.

I was listening to a podcast this week. Famous bootstrapped founder. Built a company 20 years ago that everyone used to talk about. Technically brilliant.

He's on there talking about how excited he is about AI. Using agents to debug code. Review security reports. Analyze logs.

And I'm thinking: bro, this was the conversation a year ago.

He's discovering agent mode in late 2025. Being amazed that AI can use a debugger. Talking about "neat ideas" they might ship but "probably won't."

Meanwhile his actual products? Dead. Not dying - dead. No new company is evaluating them. His customer base is people who signed up in 2015 and forgot to cancel.

He's using AI to maintain a corpse more efficiently.

That's what happens when you stop asking hard questions. You retreat into craft. Perfecting details nobody cares about. Finding meaning in the work while the work stops mattering.

It's not wrong. It's just over.

The guy has freedom. Profitable company, no VC, no pressure. But he's using freedom to polish legacy software and record podcasts about debugging.

I just killed my first business because I asked "does this serve my life?"

He's not asking "does this product need to exist?"

One question is strategic. One is cope.

Freedom is a prerequisite, not a destination. Optionality that sits unused is just potential energy going nowhere.

So I've been asking: what do I actually want to build?

Not businesses. Capabilities. Things that compound no matter what AI does next.

Every outcome that matters comes down to a conversation.

I'm decent - but not great. I want to be dangerous.

Started doing reps intentionally - real stakes, real money on the table, from just a conversation at a restaurant or a car rental shop in France, watching what works.

This can't be automated. It's human, it's timing, it's reading the room.

Started because Canada rewards bilingual. Quebec has angles.

But the deeper I got, the more I realized: French opens Europe, Africa, chunks of the Middle East.

The assumption that English is the only language that matters? I'm not sure that holds for the next 30 years.

The post-WW2 order is cracking. Learning something with weight outside the Anglosphere feels less like a hobby and more like insurance.

20 minutes a day. Every day. Just showing up.

Not trading - I lost $300K on that already, lesson learned.

Capital allocation. Pattern recognition. Understanding what I'm looking at when I evaluate a company. Takes thousands of hours. I'm at maybe 200. Long way to go.

Boxing probably. Something where you can't fake the reps.

You either trained or you didn't, and everyone knows the second you step in.

I want that feedback loop somewhere in my life.

I already go to gym, so this is not really about staying fit. It’s more about knowing that I can punch someone in the face if I can.

It matters in the next few decades for survival, it matters for being in a room and not being intimidated. Works in both business and personal life.

None of this is "productive" in the way people talk about productivity. No direct revenue. Won't make a Twitter thread.

But it's mine. It compounds. And nobody can take it.

Freedom isn't about not working.

It's about choosing the work.

For years I worked on whatever other people needed from me. Customers calling at 5am. Employees going rogue. Fires everywhere.

Now I work on what I choose. Skills I want. Businesses designed around my life instead of despite it.

That founder on the podcast? He has the same freedom. Profitable, no VC, no obligations.

But he's using it to maintain. To polish. To craft things that don't matter anymore.

I'm using mine to ask harder questions. Kill what's dying. Build what survives.

Winter used to feel like a cage. Now it's a choice I'm making—and one I can change by Friday if I want.

That's the difference.

The SimpleDirect email went out Thursday. By Sunday I'd moved on completely.

Five years of building. Four days to close the chapter.

Not because I'm cold. Because I'd already grieved it - months of it, probably years - while I was still running it.

By the time I hit send, the decision was already made. The email was just paperwork.

If you're sitting on something like that - a decision you know you need to make, something that would free you, but you keep putting it off - you're paying the cost anyway. The stress. The weight. The 5am calls.

The email is just the announcement.

Might as well send it.

George