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Go back thirty years

What would you do differently?


Planted September 14, 2026

While on our dog walk last night, my 13 year old asked a question that I’ve played with a few times before:

What would you do if you were transported into your body 30 years back in time with all of your memories from now?

I’ve explored this thought experiment before but coming from him, it stuck around a bit longer. He was born when I was thirty, so I would be his age and back in Belfast. We chatted back and forth a bit but I woke up thinking about it still this morning.

I guess, first off, there would be some financial decisions that would be different. I’d buy Apple and Google stock when they were low, I’d buy Bitcoin when I first heard about it back in 2010 and hold it and I’d probably aim to have enough money to buy property after the 2008 crash.

I’d build websites for local companies in the mid-90s, initially with Perl and then jumping to PHP and Python when they became available. Even my meager web design skills would seem outstanding in a world of GIFs and HTML tables.

But I think I would still go deep on Maths like I did the first time around. Though maybe I’d try to combine Computer Science and Physics for my degree. I’d still freelance in the background, building web sites and web apps, steadily growing and building that muscle.

I’d play more D&D and do Jujitsu. Two things that could grow over time and be sustainable to my venerable age now. Using both to be steady counter-balances to work and sources of friendships and relationships.

I think I’d still create educational content - I’d blog before it was cool and ride that wave, I’d dive into YouTube as it was starting and ride that wave, I’d build iPhone apps and web apps, I’d be an early voice talking about the importance of portfolio above credentials.

I don’t think I’d be interested in founding or running a large company. I’m still heavily influenced by Paul Jarvis’ “Company of One” but maybe I’d have a small team of editors and co-developers to make things less lonely.

I think I’d still be in Northern Ireland or England - I don’t think I’d want to be in the US - and, though that might initially be damaging, it would be less relevant as years went on.

The more I dived into it, the more I realised that the life I was creating in this thought experiment wasn’t very different from the life I’m living right now. I might have got to where I am quicker but the end goal wouldn’t be far from where I stand now. That felt pretty surprising.

I get to work for myself and, while that doesn’t scale very well all the time, it does give me a level of freedom and automomy that I’ve come to appreciate and value. I get to work alongside different teams and technologies and business domains - learning and growing from each engagement - and that helps my ADHD to stay on track.

I noticed that my fantasy life leaned in on small, repeatable actions, faithfully carried out over time. I feel challenged to reflect on which of those can be done now - here in this time-line.

In a world where content machines are being driven by LLMs and vibe-coded apps are everywhere - what are the small repeatable actions that I can take that will help me in the next 10, 20, 30 years to build more of the life I want.

  • In relationships. Meaningful, dedicated time with my wife, kids and friends.
  • In health, continuing to go to the gym - even on days when I can’t be bothered.
  • In writing, showing up here and elsewhere to create and write. To build that muscle and give it real time and space.
  • In work, continuing to work with clients, building and delivering courses that help folks to meet their goals.

Maybe I need to build more side-projects - see things through to completion, give things more space and time. Mostly though, I feel grateful that I have somehow stumbled into a life that I’m happy to live, with people I’m priviledged to share it with and work that is interesting, varied and purposeful.

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