Where Have All The Cowboys Gone?
When inspiration and dysfunction are the same thing
It was spring 2017.
My first time back in New York City since I was a child.
I’d spent most of the week trapped in the basement office of a mildly megalomaniacal client in Brooklyn. Five days with nothing but darkness, coffee and a coding editor.
Now I finally had a day to myself. But I realised something: I had absolutely no idea how to casually “do” New York.
I find big cities hard to just freestyle.
There’s too much history. Too much mythology. Too many places you’re apparently supposed to care about.
So I just wandered.
Eventually I drifted into Central Park and remembered that John Lennon had been shot nearby.
Curiosity took over.
A few minutes later I found myself standing in Strawberry Fields staring down at the famous “Imagine” mosaic.
A lone busker sat nearby with an acoustic guitar quietly playing Blackbird.
And to my surprise, I found the whole thing strangely moving.
Not because I’m some Beatles obsessive. I’m more of a punk guy.
But there was something oddly beautiful about strangers from all over the world silently gathering around the memory of one person and his art.
A few days later I got home and told my girlfriend at the time about the trip.
“So what was your favourite part?” she asked.
“The Lennon memorial.”
The second I said it her expression changed.
Not mildly annoyed.
Disgusted.
Real disgust.
“You know he beat his wife, right?”
No.
I really didn’t.
And she was furious with me for not knowing.
After that conversation, I wasn’t entirely sure what I was supposed to do with the feeling I’d had standing in Strawberry Fields.
Because the older I get, the more I realise that a lot of our most inspirational figures are also cautionary tales.
Die a hero, or live long enough to become the villain…
One of my first heroes growing up was Arnold Schwarzenegger.
Terminator 2.
Predator.
Total Recall.
I watched all of them obsessively.
The accent.
The terrible puns.
That ridiculous physique.
He felt less like a real human being and more like some kind of living and breathing mythological creature.
And the older I got, the more inspiring he became.
Underneath all the action movie nonsense was someone with almost frightening levels of self-belief.
Become Mr Universe?
Done.
Become an A-list movie star?
Easy.
Become Governor of California?
OK.
And the thing that fascinated me most was that none of it felt accidental. He worked for it relentlessly.
Even now, I still find that inspiring.
But there was a catch.
Of course there was.
The stories started surfacing.
The affairs.
The cheating.
The child he’d secretly fathered with his housekeeper.
It’s strange feeling personally disappointed by someone you’ve never actually met.
But it upset me.
The charisma trap
In tech, this stuff becomes especially strange because the industry still seems obsessed with mythologising difficult people.
The shadow of Steve Jobs still hangs over almost everything.
The man who helped build Apple into one of the most influential companies on earth also publicly humiliated employees, denied paternity of his daughter for years and was infamous for emotional volatility.
And yet people still talk about him with something close to reverence.
I’ve worked with managers who clearly believed cruelty was a legitimate motivational strategy because they thought that’s what visionary leadership was supposed to look like.
Then there’s Elon Musk.
At this point just mentioning his name is usually enough to split a room in half.
Visionary.
Fraud.
Genius.
Narcissist.
Depending on who you ask, he’s either building the future or actively making it worse.
These days, I find it hard to identify a genuinely exceptional public figure who isn’t deeply flawed in some meaningful way.
Which raises an uncomfortable possibility: maybe the traits that allow people to become extraordinary are often the very same traits that eventually make them difficult to live with.
Maybe that’s why I still don’t fully know what to do with the feeling I had standing in Strawberry Fields that afternoon.