I Kept Winning the Wrong Game

When getting what you thought you wanted leaves you empty.

Photo by Mohammad Hoseini Rad on Unsplash

I still remember getting the call in my home office.

“You’re being promoted to Vice President. You’ll make $xxx, xxx a year. We’re so excited for you.”

I should have felt excitement. Or relief. Or something.

But I didn’t.

I felt emptiness.

It was almost an out-of-body experience, like I was hovering above myself, listening to someone else’s life being announced back to him.

And underneath the numbness, there was something even harder to admit:

terror.

I had worked hard to get there. I knew how to do the job. I knew how to perform. I knew how to keep pushing. I knew how to make people believe in me.

But there was also a deeper part of me that did not want this life.

That was hoping someone else would make the decision for me to reclaim my life. Quietly hoping they would close the door so I would not have to be the one to walk away.

But the doors never closed. They kept opening.

The promotions came.
The money went up.
The titles got better.
The reasons to keep going kept stacking up.

And the gap between who I was and who I was becoming kept getting wider.

When I hung up the phone, I lay on my back and stared at the ceiling.

That has become a familiar posture for me over the last few years.

Staring.
Numb.
Too exhausted to keep going, but too scared to stop.

For a long time, I ignored that quiet part of me asking for something different.

I buried it under ambition.
Under optimization.
Under performance.
Under the next plan, the next job, the next title, the next comp package, the next story about why this next move would finally make everything feel right.

I told myself the next opportunity would fix it.
That if I chose better, performed better, optimized harder, I would finally arrive somewhere that felt like peace.

But nothing changed.

The house changed.
The comp changed.
The title changed.

The emptiness remained.

The most confusing part was that nothing was outwardly wrong.

I was succeeding.
People respected me.
More doors were opening, not fewer.

That made it harder to admit that something inside me was dying, but I’m losing the energy to keep lying.

Not because I had some epiphany. That would be too clean.

I’m just too tired to keep doing this the same way.

I think the most painful truth is not that I built a successful career. It’s that I used my career to avoid myself.

I used it to stay distracted.
To stay in motion.
To avoid the harder questions waiting underneath all of it.

Questions like:

What if I’m living someone else’s life?

What if achievement has become my way of hiding from myself?

What if all this striving has been less about desire and more about fear?

On paper, things kept working. In reality, I was losing myself.

It is terrifying to wake up in a life you built with your own hands, only to find it unrecognizable.

And for some reason, I can’t ignore it as easily as I used to.

That may be the hardest part.

When your identity is built on being competent, ambitious, high-performing, and always moving forward, even a small crack can feel like your whole world is collapsing.

I don’t fully know what’s on the other side of this.

I just know that something deep in me is asking me to stop abandoning myself.

To stop using achievement to numb out.
To stop confusing momentum with alignment.
To stop waiting for a closed door to make the decision for me.

For the first time in my life, I am trying to sit with the pain instead of immediately turning it into a plan.

That doesn’t feel brave.
It feels disorienting.
It feels unstable.
It feels like risking the identity that has carried me for a very long time.

But it also feels more honest than anything I’ve done in years.

And for now,
that honesty is enough.

---

with gratitude,

Ben

PS: thanks to Scott Barker, someone I’ve never met, who gave me the courage to write from a place of truth.