How I Built a Business I Don’t Want to Retire From

It’s just gone six in the morning. I’ve made a coffee, and I’ve sat down to write, like I do every day before anyone in Europe is even awake. In a couple of hours I’ll have a call or two, which is the real work as far as I’m concerned, a client and maybe someone thinking about working with me. By lunch I’ll be done. This afternoon I’ll be out on the water in an outrigger canoe.

And if you asked me when I plan to retire, when I plan to stop doing all of this, my honest answer is never.

That’s new. A few years ago I’d have given you a completely different answer.

The reframe (past self)

Back then, if you’d asked me the same question, I’d have given you a number. A figure in a bank account, a date, a finish line. I was running a different business, and I was good at it. The revenue was there, the clients were there. On paper it was working.

But I was running on empty. I had a post-it in a frame on my desk that said “work is supposed to be enjoyable”, and I’d got to the point where it had stopped doing that. Every version of the future I could picture was just more of the same. More clients, more calls, longer days to fit it all in. So of course I wanted to retire. Retiring was the escape hatch.

The wrong belief

Here’s the thing I’d absorbed without ever questioning it. I thought building a business meant scaling it. More people, more overhead, more systems running, so that one day you could sell the whole thing and walk away. That was the only model I’d really been shown. Work hard for years, sacrifice the evenings and the weekends and the birthdays, hit the number, then stop.

The reward for building a business was getting to leave it. And I’d quietly built my whole idea of success around an exit.

The turning question

Then one day I asked myself a different question. Not “how do I scale this?”, but “what do I actually want my Tuesday to look like?” Not the holiday. Not someday. An ordinary Tuesday.

Because you can tell what matters to someone by looking at their calendar, and mine was full of things I was doing so that one day I could stop. That question is the reason I run the business I run now, from a small island in the Pacific, in about four hours a day.

Point 1: Design the life first

So the first thing I did, and the first thing I’d put to you, is this. Design the life first, then build the business around it.

Most people do it the other way round. They pick a business model, follow someone else’s playbook, and then squeeze whatever life is left into the gaps. I did exactly that for years. The problem is the model hands you a life, and you just accept it.

So I flipped it. I worked out the shape of the days I wanted first. Writing in the morning. Out on the water. French. Dinner with my partner. Weekends that are actually mine. Then I made the business fit around those, instead of the other way round.

Point 2: Automate everything except the part you love

The second thing was working out which part of the work I’d never want to give away. And for me that’s the conversations. Talking to clients, and talking to the people thinking about becoming clients. That’s the part I enjoy most, and it’s the part I’m best at.

So here’s what I did. I automated almost everything else. The admin, the follow-up, the scheduling, the proposals, the invoicing. The bits that used to eat my day and that I never enjoyed anyway. That’s the exact work I do for clients, so I did it for myself first.

And what’s left, once all of that runs on its own, is the part I actually like. The conversations. I get to spend my few hours a day talking to interesting people about their business, and almost nothing else.

That’s the whole point, really, and it’s the part I want you to take away. It isn’t “get yourself out of your business”. It’s the opposite. Automate the parts that drain you, so you’re left doing more of the part that’s actually you. You can do exactly the same thing in your own business, whatever the enjoyable part is for you. Keep that, and hand the rest to the systems.

Point 3: Set rules and constraints (the ama)

The third thing is rules. Constraints.

When the only thing you care about is the finish line, the exit, the retirement, you’ll do almost anything to get there faster. The journey stops mattering and the outcome takes over, and that’s how people end up hating a business they built.

So I took the finish line away. There’s no exit to aim at, which means there’s only the journey, and the journey has to be good. The way you make it good is constraints. My business is capped at about four hours a day, and I stop at the cap even when it’s flowing. One thing a day that actually moves the needle, revenue, the real work, or a piece of content, and the admin is just warm-up. Weekends are off. And here’s the part people miss: the constraint doesn’t shrink the business, it forces every part of it to earn its place.

Where I live, people cross huge stretches of open ocean in outrigger canoes. The thing that makes that possible is the ama, the little float that sits out to the side. It isn’t glamorous, nobody’s looking at it, but it’s the reason the canoe doesn’t tip over.

In a business, your systems and your automations are the ama. They aren’t the point. They’re the thing that lets you go the distance without capsizing. Build the life first, and let the systems carry the business.

Point 4: No finish line, just seasons

The last piece took me longest to understand.

For a long time my goal was basically to escape. To get away from the burnout, away from the version of work that was crushing me. Escaping is a real goal, but it only works once. The day you’ve escaped, it’s done. And “the person who got out” isn’t a plan for the next twenty years. It’s a reaction.

So I had to work out what I was building towards, not just what I’d run from. What I landed on is that the work itself stays the same, and only the medium changes. Whether I’m doing a custom build for one client, packaging that into a product, or writing it into a book, it’s the same thing underneath. Helping someone turn chaos into a system that runs without them.

The format will keep changing. The thing I’m actually doing won’t. And when the thing you’re actually doing is something you’d happily do for free, retirement stops making sense. Retirement is what you reach for when work is something you’d never do unless you were paid. Replace that with work that’s genuinely yours, and the question just dissolves.

So that’s what I’d leave you with, whatever you do for a living. Find the part of your work that feels easy and natural to you, the part other people find hard, and pull more and more of it into your business until it’s most of what you do. Design the days first. Put rules around them. Let the systems be the float, not the point.

Do that, and you might end up where I have. Building something you’ve got no interest in retiring from.

If you want to see where your own business is doing the opposite, where it still runs through you for everything, I’ve got a free Business Automation Audit on my site. It takes about twenty minutes, and it’ll show you exactly which parts are quietly depending on you and what to fix first. Link’s below.

I’m also writing all of this up properly in my book, Automated, which is out on the 16th of July.

Take what’s useful here and leave the rest. I’ll see you in the next one.