Success Gives You Everything Except a Reason to Wake Up

Happy Thursday, friends!

I didn’t expect the hardest part of success to come after the success itself.

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Success Gives You Everything Except a Reason to Wake Up

Somewhere between my old life and whatever comes next

There’s a strange kind of silence you hear only after you’ve “made it.”

It’s not the peaceful kind of silence, like waking up before sunrise or standing alone on an empty beach. It’s the hollow kind. The kind that echoes. The kind that sounds like purpose evaporating.

Nothing feels more uncomfortable than being the person who says:

“I have everything I ever wanted… and yet I feel lost.”

It sounds arrogant. Detached. Even ungrateful.

But it’s also the truth.

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Naval says:

“Desire is a contract to be unhappy until you get what you want.”

But what he doesn’t mention is this:

You’re also unhappy after you get it, because then there’s nothing left to want.

It’s a double loss.

When money is no longer the goal and status no longer excites you, everything becomes optional.
And humans don’t do well when everything is optional.
We need friction.
We need constraints.
We need something to push against.

Total freedom is a cute idea until you actually have it.
Then it becomes a void.

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The Guilt of “Making It” Before Everyone Else

Here’s the part nobody talks about.

When you surpass your peers—financially, career-wise, status-wise—there’s a kind of guilt that creeps in.
It whispers:

“Who do you think you are?”
“Why you?”
“Don’t get too comfortable, this can vanish.”

Success isolates you.
Your friends can’t relate.
Your family can’t relate.
Most people assume your problems evaporate with your bank balance.

But money doesn’t solve identity problems.
It intensifies them.

I used to feel connected.
Now I feel observed.

I used to feel like part of the group.
Now I feel like an outlier.

Being “better off” financially does not feel like being better.
Sometimes it feels like being apart.
Or worse: being completely alone.

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The Misleading Fantasy of “When I Have Time, I’ll Finally Be Happy”

So many people dream of financial freedom.

Let me tell you the punchline:

You will be ecstatic for 3 months. Then you will be bored. Then you will be lost.

I traveled.
I ate whatever I wanted.
I bought things.
I slept in.
I tried hobbies.
I worked out.
I “relaxed.”

It was great… until it wasn’t.

You can only vacation for so long before vacation becomes the new normal, and normal becomes empty.

Humans aren’t built for unlimited leisure.

You think you want paradise.
What you really want is purpose.

The thing is, when you’re on your own, you stop dreaming about the beach holidays, because you know that you can go whenever you want, and this automatically leads to that you have no need for it anymore.

The beach holiday was simply a metaphor for an escape. But now you don’t need to escape. You are free.

Which leads me to this quote by Worst Contrarian:

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The Problem Isn’t Motivation. It’s Meaning.

5 years ago, I kept trying to outrun the emptiness:

• New business ideas

• New hobbies

• New cities

• New books

• New distractions

• New “quests” that didn’t feel like quests

Nothing worked.

Because the void wasn’t external.
It wasn’t about what I was doing.

It was about why I was doing it.

Or rather, why I wasn’t.

I realized that every goal I used to have was tied to survival:

• escape my childhood

• make money

• prove myself

• be “somebody”

• climb

• build

• win

Once the survival layer was handled, the entire operating system broke.

Now the challenge isn’t making money.
It’s making meaning.

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I’m Supposed to Be Happy. So Why Do I Feel Like Something’s Missing?

I’ve heard Olympic athletes describe this.
I’ve heard founders describe this.
I’ve heard artists describe this.

The moment after the biggest moment of your life is…
weird.

You look around and realize:

There is no parade.
There is no final score.
There is no finish line.

Just more life.

Just more hours to fill.

Sixteen of them, every day.

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The Embarrassing Truth: I Don’t Know What to Do Next

I could invest. But to what end?
I could travel forever. But for what purpose?
I could consume. But consumption is numbing, not fulfilling.
I could chase status. But that game never ends.

The real question is:

What is worth doing when nothing is required?

And I don’t know the answer.

Not yet.

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So What Now?

Honestly?

I don’t know.

Maybe I need to build something again.
Maybe I need to help people.
Maybe I need to invest in something else?
Maybe I need to move to another country?
Maybe I need to learn, or teach, or create, or wander.
Maybe I need friction.
Maybe I need to confront myself.

If you’re reading this and you’ve ever felt the same way, whether you’re successful, struggling, or somewhere in between, just know:

You’re not crazy.
You’re not spoiled.
You’re not broken.

You’re human.

And being human means constantly rediscovering your reason to be.

I’m somewhere in that rediscovery right now.

I don’t know where it leads.

But for the first time in a long time…
I’m willing to find out.

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See you around, anon.

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