The arrival lounge that never opens

Life’s a journey, not a destination. I bet you’ve seen it somewhere: on a mug, a fridge magnet, probably a motivational poster in someone’s downstairs loo. I’ve always believed it. I never had a five-year plan. I couldn’t understand people who did. I admire that sense of purpose; I’ve just never been able to do it myself.

And yet, looking back over forty-odd years of work and life, nearly every decade had a moment where part of me still thought I was about to arrive. Just one more promotion, one more qualification, one more product launch, and then I’d be there. Settled. Sorted. Done.

I never got there. Every time I turned the corner, there was more road. It was never a shock. Knowing that life’s a journey doesn’t stop you from glancing up for the finish line now and then. It just means you laugh at yourself when, of course, it isn’t there.

Five decades of nearly arriving

My twenties. I left Polytechnic with a scraped HND, having been dumped off the degree course I started on. Apparently, attendance, coursework and exams weren’t optional. I tried for a few software jobs, but no offers. So I decided to stop looking and make a career out of my holiday job as a car mechanic. And then, a call from the final place I’d interviewed and a job as a junior software engineer. The destination from there was obvious: become a real engineer. Senior. Trusted with the difficult stuff. I got there, and found that writing great code mattered far less than knowing what was worth building.

My thirties. The goal became leading the team. I grew it from one developer to six. I created a windowed GUI on DOS before there was Windows. We took a product out of 1970s command-line computing onto that and eventually onto Windows itself. Surely that was arriving? It wasn’t. The real problems were about people, products and customers, not bits and bytes.

My forties. Technical Director. The title I’d been chasing. I remember thinking, right, that’s it, I’ve made it. Within a year I was more interested in the Internet, marketing, websites, content and where the whole business was going than in the title on my door.

My fifties. General Manager, an MBA with distinction, a business growing from £1M towards £2M, a pandemic survived (just). This, finally, was the summit. Then it became clear the group wasn’t going to invest in what we’d built. They’d sucked out the IP and cash that they wanted, and we were being ignored to death. So, after forty years, I walked away. Not the ending I’d pictured.

My sixties. I thought this was meant to be the winding-down bit. Instead I’m a CTO at a start-up, a charity trustee, a solopreneur on a family history app, non-exec, building an app and company with AI, and learning faster than I have in years. No arrival in sight. I wouldn’t want one.

Becoming, not arriving

David Bowie, a man who reinvented himself more times than most of us change our socks, once described ageing as an extraordinary process in which “you become the person you always should have been.”

I love that, because it flips the whole thing. Ageing isn’t drifting away from who you were. It’s drifting towards who you are. Each decade strips away a bit more of the stuff you thought you were supposed to want.

For me, that meant learning that titles don’t motivate me. Money neither. Don’t get me wrong: I love money, and I’ve been fortunate enough to earn enough not to worry about it too much. And I don’t take that privilege lightly. Money buys me cars, tech, and beer, but it doesn’t motivate me to do a job that’s dull or unrewarding. What I actually need is meaning, freedom and people I like. None of that came as a revelation. But each decade made it a little clearer and a little more mine.

The twenty-year-old with the scraped HND wasn’t a worse version of me. He was an early draft with a lot of scribbled notes in the margin. Every decade has been another edition, and the manuscript still isn’t finished.

Stay unfinished

My tagline is stay unfinished. I wrote it as part of an early version of my weirdfruit manifesto, as a reminder of something I’ve always believed and still occasionally forget in the moment.

Here’s what I’d say to anyone still waiting to arrive:

  • Stop measuring yourself against a finish line. It moves every time you get close, so it’s a terrible metric. Instead, measure how far you’ve come and how much you’ve learned along the way. That measure only ever goes up.
  • Enjoy the corners, not just the straight. The best bits of my career were the moments I didn’t know what came next. To channel Bowie again: “When you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.”
  • Let the destination change. The goal you set at 25 was written by someone with half the information you have now. Planned destinations are usually at the end of straight roads. Of course, the motorway is quicker, but nobody ever told a good story about the motorway.
  • Notice who you’re becoming. That’s the real progress, and it doesn’t show up on a CV. Every now and then, stop and compare yourself with who you were five years ago. What do you care about now? What have you let go of? What will you never put up with again? That’s the story worth telling, even if it’s only to yourself.

The road keeps going. Thank goodness. If I’d ever actually arrived, I suspect I’d have been bored within a fortnight.