November 2026
Successful at the Wrong Thing
Imagining a wealthy entrepreneur who might have been happier writing poetry led me to a simpler question: do I even want the life I’m working towards?
I’ve been imagining a man who becomes extremely wealthy.
A very successful entrepreneur.
He’s spent years moving in that direction. Built the business. Made the thing work.
But somewhere in him there’s this other inclination. To explore. Write. Maybe be a poet of love or something.
And perhaps expressing that part of himself would have given him a contentment he never found in the business.
He got what he was supposed to want, but missed what actually made him feel alive.
That’s the bit that interests me.
You could spend a considerable amount of your life doing something you never really wanted to spend your days doing.
The fear was there. The idea of success was there. A direction you could explain and defend.
Then you actually have to live the days.
I recognise some of this in myself.
I don’t have an enormous desire for material things. Some desire, yes. But there aren’t that many things I’m desperate to own.
So what am I moving towards?
Do I even want this?
At a logical level. Before I start working out how to get it.
Because I quite like reasoning from first principles. Pulling something apart. Understanding the underlying mechanics. Figuring out how it could work.
But the goal deserves that treatment too.
Why do I want it? What do I think it will give me? Am I just doing it to fit in?
Does it feel aligned with me, or does it fit a picture of what I’m supposed to be?
Sometimes there’s a strong feeling before I can explain much of it. I’m drawn towards something, or I feel myself resisting it.
Then I can look at the thinking around it. What am I telling myself? What assumptions am I carrying?
One of those assumptions might be that I have to be one kind of person.
An entrepreneur.
A poet.
A serious scientific person.
A man making stupid cartoons on the internet.
Pick one, apparently.
But some of the moments that feel most like me happen when those things come together.
I have an idea that’s so stupid it makes me laugh. Then I start reasoning through it from first principles.
Could this actually work?
There’s something serious to understand. There’s also a ridiculous way to express it. The thinking and the cartoon can be part of the same thing.
Scientific, creative, jokey and fun, all in one.
Yeah. That feels a tad like me.
I don’t need to remove the reasoning to keep the silliness. I enjoy both.
Which brings me back to our wealthy man.
What stops him from keeping the money and writing some poetry now?
Maybe he’s become so attached to being the successful businessman that anything outside that identity feels difficult to allow.
But why can’t he be a bit of a poet, and also a ruthless entrepreneurial businessman at times?
He can write something and find out whether he enjoys it.
The poet was only an example anyway. The interesting part is whatever he keeps feeling drawn towards while explaining why he should be doing something else.
And for me, this keeps coming back to a very ordinary question.
Do I love my normal fucking day?
Monday. Tuesday. Wednesday. Thursday. Friday. Saturday. Sunday.
Do I actually love the days I’m spending my life in?
What am I doing during them? What interests me? What do I keep wanting to explore? Where do I feel myself come alive?
I’m curious about what changes when I take those questions seriously.
What am I actually spending my days doing? Am I choosing it because I want to, or because I’ve become attached to being the sort of person who does it?
Do I even want this?
Do I want the actual life that comes with it?
Because I’m going to have to get up on Monday and live it.