Hey Little Pineapple,

I had this conversation with a friend recently.
At some point we started talking about work because of course we were.

We were talking about me living in Bali, doing the whole digital nomad thing and him sitting in Poland, running a customer service team.

He told me he really likes the job.
Feels good at it.
Like he's making a difference.

All the things you want to feel about work, right?

Here's the kicker: he used to be a business owner.

He had his own thing. Spent years being his own boss.
And then... he decided he didn't want to do it anymore.

The struggle everyone hides

For years, he carried this weight.
The Instagram version of success told him he had to have his own business.
LinkedIn tells all of us that being your own boss was the only real win.

He couldn't admit it to anyone.
How do you tell people you want to give up the thing that is supposedly THE win in the career game?

On paper, he had what most people wanted.
In reality, he was exhausted.

He used to work late nights and constantly thinking about his business.
Weekends? Forget it.

But what I felt the most was when he told me he missed his daughter bedtime multiple times because there was something to do in the company.

I mean, fucking hell, I've heard sadness in my life a lot, but this one sentence carried so much of it I felt it deeply.

The realization that changed everything

The problem wasn't his business.

The problem was that he was playing someone else's game.

He'd been sold this idea that success meant having something of your own.
That winning the career game meant entrepreneurship or bust.
(And let's face it - we are being sold this crap on daily basis)

But when he really thought about what he wanted, it wasn't "freedom" or "being your own boss" or any of that stuff people post about.

Nonono, it was way simpler.
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Stability.
Being able to plan his time with his daughter.
With family. With friends.
Not thinking about work at 11pm on a Sunday.

So he made a choice that looked crazy to everyone else.
He shut down his business and took a job running a customer service team.

And for the first time in years, he felt like he was winning.

What this taught me about career success

That conversation stuck with me because it exposed something most people don't talk about:

In the career game no one tells you what the win condition is.
So most of us just grab someone else's and run with it.

Finally a manager = you made it
Six figures = you made it
VP on your LinkedIn = you made it
Your own business = you made it

But those aren't universal truths.
These aren't even truths - just the shit someone made up.

Usually your company.
Or Instagram.
Or your parents at dinner five years ago.

I've spent enough time talking to people about their careers to notice a pattern: the ones who feel successful aren't the ones who climbed the highest.

They're the ones who figured out what "high" even meant to them in the first place.

The questions that actually matter

That's why obsessing over hitting a specific salary number is usually the wrong move.

Not because money doesn't matter (it obviously does) but because money is a tool.
It's not the finish line. It's what gets you to the finish line.

Better questions than "how much do I want to make?":

• What do I want my average Monday to actually feel like?
• How much energy do I need left over after work?
• How much do I want to depend on one company for everything?
• How much control do I actually want over my calendar?

So we are asking not ego questions, but lifestyle questions.

What happens when you don't decide

If you don't decide what winning looks like for you, someone else will do it instead.

The company will define it. The market will define it. Someone else's ambition will define it.

And if I learned anything, If you don't define winning for yourself, you'll spend your career winning for someone else.

You can roll with this for months, even years and not even notice it that much.
But then, one day you wake up and everything looks fine on paper, but it feels wrong.
And you can't even explain why.

My friend figured it out. He's probably one of the few people I know who actually decided what his win condition was and then had the guts to choose it, even when it looked like "going backwards" to everyone else.

The question worth asking

So here's what I want you to sit with this week:

Is the ladder you're climbing even leaning against the right wall?

Because the saddest thing isn't failing to reach the top.

It's reaching the top and realizing you climbed the wrong ladder.

P.S.

If this whole newsletter made you think "shieeet, I might be playing someone else's game" you're not alone.
I help people with this exact mess.
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Reply to this email and let's figure out what your version of winning looks like.
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