All this and still not happy

...questions success can’t answer, and I wasn’t prepared to feel.
All this and still not happy

A return to basecamp

I came down from the mountain, and no one noticed.

The ambulance-chasers had moved on to fresher crises.
The summit-chasers were packing for their own ascent.
Basecamp hummed with quiet, competent people doing what they always do -
finalizing decks, rehearsing talking points, massaging the roadmap like a tired muscle.
Business as usual. As if nothing had changed. As if no one ever fell.

A few veterans raised their eyes.
The small, imperceptible nod of recognition amongst those broken inside.

At first I waited for the moment. The moment when something would change. The dawn of a new day, the start of the next chapter, the realization of something profound.

I waited.
And waited.
And nothing happened.

The world moved on, because it always does.

But I was still here.

Not broken. Not victorious.
Just… surplus.

I thought this climb would change me.

And it did.
But it didn’t prepare me for what came next.
The stillness.
The void where something should be.

Nothing prepared me for the silence to sound like screaming.


The Ancient Warning

You read the teachings. You know the answers.

The Buddha under the Bodhi tree. Marcus Aurelius in his journals.
It’s the journey, not the destination.
The work is the point.
Peace is found in acceptance. Suffering in attachment.

And the modern prophets echo the same sermon - Clear, Holiday, Ravikant.
Discipline over desire. Process over prize. Optimization as salvation.

To crave the result but not the process is to guarantee disappointment.

  • James Clear

The words are simple. Their meaning is clear.
I can quote them. I can explain them. I’ve caught myself quoting them in advice.

But knowing isn’t believing.
And believing isn’t living.

Some people say Jesus fills their heart.
I’ve read the Wikipedia summary.

I don’t want the journey anymore. I want to arrive.

But my destination can’t be found on any map.
It shifts. Moves with the tide. Recedes as I approach.

I used to believe a strong destination was like a lighthouse.
A fixed point. A guide.
Every decision became a simple question:
Does this bring me closer, or take me further away?

But what do you do when the light goes out,
and you’re left alone in the fog, on a featureless sea?


The Process vs. The Prize

All that modern Stoicism, all that talk of discipline and peace…
It was never about stillness.
It was productivity gospel.
Efficiency, not equanimity.
Status and leverage, sans crystals.

You can have anything you want, but not everything.
That’s the refrain.
Escape the messy middle. Go all-in. Double down once you’re winning.
“Passion is for amateurs.”

You can have anything,
if you’re willing to sacrifice everything.

The trick is: I already know how to sacrifice.
I’ve been doing that for years.

But when does delayed gratification become no gratification?

I’m good at the process.
Maybe even admired for it.
I can build the thing. Run the meeting. Mentor the team.
People say they need me.

But I’m not sure being needed
is the same as being alive.

Maybe I never wanted the California tech job.
Maybe I just wanted to be the kind of person
who could’ve said no to it.


The False Choice

The smart move would be to stay right here. Coast a little. Trade the chaos for calm. Quietly turn down the hours, write a little more. No one would question it. Some might even envy it.

Or I could jump. Again. Back into the fire. A messy startup. Chaos everywhere, fighting for survival… Ambition with elbows.

Burn hot. Burn fast. Burn out?

Neither choice feels honest. Both feel like lies to myself. Paths already taken.

The devil you know versus the one that’s hiring.

I’ve climbed those mountains. I’ve walked through those flames.
But I’ve never… sat still.

That stillness?
That’s what terrifies me the most.


The Man Who’s Content

Roosevelt said comparison is the thief of joy.
Moses etched it in stone.

And still.

There’s a guy I work with.
Similar path, a few years ahead.
Four kids. A loving wife. A house in the ‘burbs.
The Canadian dream, if there is such a thing.

He codes. He’s respected.
A couple meetings a day. Quiet influence behind the scenes.
He avoids the politics. He doesn’t chase status.

He just loves to build.

The kind of person who codes on weekends - not to get ahead, but because it brings him joy.

He’s the guy who’d turn down the promotion.
Who knows exactly what his perfect day looks like - and lives it, every day.

He looks content.

And that contentment?
It wrecks me.  

Softly. Without warning. In the cracks between meetings. In the quiet just before sleep. In the moments I thought were mine.

I don’t know if I envy his peace,
or if I’m terrified by it.

What if that is the dream?
And I’ve spent my whole life sprinting away from it?

What if all my striving was just a way to avoid stillness -
and he already made peace with it?

He doesn’t need to win.
And somehow, he already has.

It reminds me of this story I heard once

A guy walks back from a promotion, takes half the pay, and just says, “I’ll be poor then.”

Years later, the millionaire who stayed on the climb looks him in the eye and says, Dude, you won."

And I haven’t been able to stop thinking about that.

What if I missed something?
Something obvious. Something early.


If Not This, Then What?

Maybe this is the part where I reinvent myself.

Buy a kayak. Take up woodworking. Meditating between rare whiskies and ultra-marathons. Launch a startup with a dumb name and call it passion.

Or maybe I keep doing this. The meetings. The mentoring. The slow dance of inbox zero. Not because it fulfills me - but because it’s something.

I know the line: your job isn’t your identity. I’ve said it. I’ve believed it.
But when I’m not building, leading, fixing - what’s left?

What am I for?

I don’t want a pivot.
I want to matter.
Maybe that’s mortality quietly knocking.
Fatherhood is a daily reminder that the future isn’t yours anymore - it’s theirs.
And I’m starting to wonder if mattering isn’t a team, or a role, or even a mission.
Am I a fool for trying to matter? Is this the mortal struggle of legacy?
To be remembered, even just a little after we depart?

Maybe that’s why I write. Not because I have something to say. But because I’m afraid of disappearing.

These essays aren’t answers.
They’re breadcrumbs.

Scattered in case someone else is wandering the same trail.

Or maybe they’re just the scrawling on the asylum wall.

Proof that someone was here.
Even if they never made it out.


When they ask

They’ll ask why I’m not happy.

And I’ll nod. Say I’m just tired.
The kids have been sick.
It’s been a long quarter.
I’m due for a vacation.

Then I’ll open my calendar and see a free afternoon -
and stare at it like a photo of my teenage self.

I don’t miss him.
I understand his every choice.

But he was so sure. So certain.

I have no idea what he wants from me.

Now, I’m not sure happy even exists.

The mountain didn't care
Dear Morgan - Do I reward heroics?

What distinguishes you from other developers?

I've built data pipelines across 3 continents at petabyte scales, for over 15 years. But the data doesn't matter if we don't solve the human problems first - an AI solution that nobody uses is worthless.

Are the robots going to kill us all?

Not any time soon. At least not in the way that you've got imagined thanks to the Terminator movies. Sure somebody with a DARPA grant is always going to strap a knife/gun/flamethrower on the side of a robot - but just like in Dr.Who - right now, that robot will struggle to even get out of the room, let alone up some stairs.

But AI is going to steal my job, right?

A year ago, the whole world was convinced that AI was going to steal their job. Now, the reality is that most people are thinking 'I wish this POC at work would go a bit faster to scan these PDFs'.

When am I going to get my self-driving car?

Humans are complicated. If we invented driving today - there's NO WAY IN HELL we'd let humans do it. They get distracted. They text their friends. They drink. They make mistakes. But the reality is, all of our streets, cities (and even legal systems) have been built around these limitations. It would be surprisingly easy to build self-driving cars if there were no humans on the road. But today no one wants to take liability. If a self-driving company kills someone, who's responsible? The manufacturer? The insurance company? The software developer?