What 30 years actually teaches you

21 April 2026

There's a version of this piece I could write where I list the lessons. Cash flow is oxygen. Services are your best R&D lab. Scale is a different sport than survival. All true. All hard-won. All missing the point.

What 30 years actually teaches you isn't a list. It carves grooves.

I started my first business in 2001, right in the middle of the dot-com crash. I didn't know it was brave at the time. I just knew I'd spent five years making money for someone else and I thought I could do it for myself. Confidence, maybe. Naivety, definitely. I'm not sure I'd have gone if I'd known what was coming.

Between 2004 and 2011 I tried to build a product. Several times. Failed. Kept the services business running to stay alive, which is what bootstrappers do and what product purists sneer at. By 2010 the writing was on the wall. Half our customers were local government. The financial crisis had hit. Contracts weren't renewing. I was doing a dozen jobs that weren't coding, falling behind technically, and quietly wondering whether I still had it or even wanted it.

I did Ayahuasca in 2011. Genuinely felt I was supposed to leave tech behind. Heart wanted to. Responsibility said no. Fear said no. I had a young family, a mortgage, and honestly, I'd been my own boss so long I wasn't sure I was employable anywhere else. Not for lack of skill. Just too long outside the system.

Then came what my business partner and I called the "fuck it" conversation.

Wrap up the business and try to survive, or go all in. Take every retained earning we had, a bank loan my partner magically convinced a bank to give us in the middle of a financial crisis, a government grant, and sell an enterprise contract for a product we hadn't built yet. Four hundred thousand pounds. All of it. On something that didn't exist.

It took us about eighteen months to win a second customer. The frantic build years that followed were some of the best in my career. I am proud of what we built. Genuinely, unreservedly proud.

But here's what I've been sitting with lately. Was I brave then, or just out of options?

I think about a friend I had as a boy. Truly brave, in the way children sometimes are before they learn to calculate risk. He'd always go first. Jump the ditch. Swim the river. Climb the thing no one else would climb. I learned something about courage in his company, by watching it up close.

What he had looked effortless. What I've done over thirty years has never felt effortless. It's felt like the next available option, chosen under pressure, sometimes working out and sometimes not.

But I've started to wonder if that's actually what most courage looks like from the inside. Not the leap made in confidence. The step taken because standing still felt worse.

I started a business in a market crash. I stayed in a marriage years past its end because I wasn't prepared to be away from my boys. I bet everything on a product that didn't exist because the alternative was a slow decline. None of those felt brave in the moment. They all felt like the only path I could see.

Thirty years didn't teach me to be fearless. It taught me to act anyway, and to stop waiting until I felt ready. Because ready never really came. And still doesn't.