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The mirage of milestones…

Guest article by Matt Gilmartin

Mulling things over half a century in

I turned 50 last month. Fifty.

Some people would claim that’s the sort of thing you whisper, or at least mutter while looking pensively out of a window.

Instead, I’m sat here with a coffee feeling pretty perky. Mostly I’m thinking… really? That came around pretty quick.

I don’t feel 50. Though I’m not entirely sure what 50 is meant to feel like? Milestones are almost always anti-climactic. We attach all sorts of meaning to them. Like there’s a checkpoint somewhere and you either pass or get sent back for a retake.

Imagine if I went to bed for the final time as a 49-year-old and expected a grand download of wisdom upon waking the next day. A composed but commanding voice going “right, Matt, here’s how it all works…”

Absurd. Nothing of the sort. I’m still just doing the best I can, albeit with a slightly longer track record. But then again… that’s true of every day.

Turn 50 and suddenly you’re subjected to these sorts of questions thick and fast: What have you achieved? What’s your biggest regret? Have you stretched this morning?

Oh for goodness sake calm down. I stretch plenty. In fact, I’m stretching right now. My brain and memory, to be exact. Nimble as ever.

The world I was born into looks absolutely nothing like the one we’re in now. No WWW back then. No siree. If you wanted to know something you read a book or asked a human. If you wanted to speak to someone, you either rang the landline and hoped for the best or knocked on their door like a civilised soul.

Now we’ve got the entire universe in our pockets. Though I still can’t get decent signal in parts of Lincolnshire. Make that make sense.

You don’t really clock these changes as they happen. Granted, the first iPhone and the first AI chatbot and those sorts of things stand out. They’re ‘milestones’ I suppose. But for the most part, change is small-scale and iterative. Then one day you realise you’re running a business in a world that didn’t exist when you started your career.

Mildly terrifying? Yeah. Incredibly exciting? Also yeah.

I’ve grown up, bumbled through, switched on, worked hard, fallen in love, had kids, raised them well (I hope), walked the dogs, drank coffee, drank beer, drank water, travelled, stretched (a-ha!), furrowed my brows in bemusement, creased my cheeks in laughter, and all sorts else.

Hitting 50 doesn’t give you some fresh perspective. The little gains you make along the way do that.

I’ve made enough decisions by this point to know that not all of them will be good ones. Some are, admittedly, excellent. Some are, well… let’s chalk them up as character-building. I’ve been around long enough to know not everything needs to be optimised, scaled, or turned into a plan.

Most things aren’t as permanent as they feel at the time. Problems pass, wins fade, and new challenges sprout up just as you’re getting comfortable. That’s the game. And I’m generally pretty pleased to be playing it.

As for what comes next… no idea. If the last 20 years are anything to go by, the next 20 will be faster, noisier, and probably full of things we haven’t even thought of yet. AI will get smarter, businesses will keep adapting, and someone somewhere will invent something that makes us all wonder how we ever lived without it.

And through all of that, I suspect the job remains broadly the same: Turn up. Do your best. Try not to be an idiot too often.

So yes, 50. No midlife crisis to report. I wonder if that sudden urge to buy a sports car will hit me real soon. For now, I’ll make do with gratitude. I’ve been around the block a bit, learned a few things, and still have plenty left to figure out. That’s quite alright with me.

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