A birthday dispatch from someone who just turned 55 and isn’t quite sure how that happened.
“He who has a why to live for can bear almost any how.”
Friedrich Nietzsche
So here it is. Another birthday.
I’ve now reached the curious milestone of 55, and frankly, it’s come as a bit of a shock.
Some part of me is still waiting to feel like a proper grown-up. I remember when I used to think 55 was ancient. You’d have a caravan, knee problems, and opinions about curtain fabric. That version of 55 wasn’t wearing Converse or trying to start a podcast from a walk across Spain. And yet… here we are.
Even more surreal: I’ll be 60 in five years. Sixty. SIXTY. That number used to belong to grandparents and old-school policemen with moustaches and proper trousers. Now it belongs to me in five years.
So yes, I’m having the traditional birthday spiral: What have I done? What am I doing? How did I get here? And is it too late to sort it all out?
The External Cheerleader, The Internal Critic
I’ve always been excellent at pumping other people up. Genuinely, I’m Olympic-level when it comes to encouraging friends. You’ve got a plan? I’ll build you a logo, write your launch copy, and make you believe you were destined for greatness.
But for myself? That same energy vanishes. I become hyper-sceptical, suddenly obsessed with evidence and outcomes.
It’s maddening. Especially today. Birthdays pull focus like that.
You start to tally up what hasn’t stuck. All the things that nearly took off, the projects that flickered and faded, the doors that opened just enough to show you what was inside before slamming shut.
That’s the pattern I know too well. And the voice that narrates it? That voice is me. Calm, quiet, persistent. Telling me: “Don’t bother. You’ve done this before. Nothing sticks.”
But here’s the twist: I know that voice is lying. It’s fear dressed up as insight. And the only thing keeping it alive… is me.
The Nietzsche Problem
Nietzsche once wrote, “He who has a why to live for can bear almost any how.”
He wasn’t talking about midlife self-employment blues, or navigating YouTube algorithms, or trying to pitch a podcast about sacred storytelling to a world drunk on viral nonsense, but still. It lands.
The ‘why’ behind what I do: walking, writing, talking, connecting, that’s still real. Still intact. It just gets buried under all the perceived expectations.
The ones that say:
- You should be further along by now.
- You should have figured it out.
- You should be more successful.
But who said that? Some ghost version of 55-year-old me I dreamt up when I was 28 and living off service station pasties? That guy had no idea what life would look like now.
The problem is never the mountain ahead. It’s always the pebble in your shoe. That small, persistent narrative that tells you not to bother — because you’ve already run out of time.
But if you’re still walking, you haven’t.
So What Now?
Maybe I stop trying to convince myself that optimism has to feel like certainty. Maybe it’s softer than that. Maybe it’s just willingness. A bit of breath in the lungs. Enough belief to get up and try again.
Not because this time will be different. But because this time is still worth doing.
And when I catch myself spiralling about age, and time, and that fact I’ll soon be closer to 60 than 50, I’ll remind myself: everything I’ve loved, built, and learned… I did after 30. Much of it after 40. So who says 55 is the epilogue?
Maybe it’s just Part Three.
So yes. I’m 55. I’m bewildered by that. But I’m here. Still walking. Still wondering.
Still trying to find a voice that’s kind enough to speak inward, not just outward.
If you’re doing the same, keep going. You’re not behind. You’re just between chapters.
Buen Camino,
Darren
