Stop chasing freedom...

What Are You Really After?

The thought crossed my mind this week — maybe I won’t put a letter out. Maybe I should really    embrace the unhurried life.
And I would’ve been fine with that.

But a conversation with Nick Simpson (who’s quickly becoming a regular here) wouldn’t leave me alone. We were talking about freedom — that thing so many entrepreneurs can’t stop chasing.

I realized: most of us aren’t satisfied because we’re chasing the wrong thing.
And it’s surprisingly it’s not money.
It’s the freedom we believe the money will buy.

Or at least, that’s what we tell ourselves.
If I’m honest, a lot of us aren’t chasing anything — we’re running. Running from who we used to be. Running from our thoughts, our emotions.

The Problem With Freedom

What is true freedom?

I don’t think it exists — not the way we picture it.
Unless you’re born in the middle of the woods to a single mom, who immediately dies, no social security number, never meet another human, no one to be responsible for, nothing tying you to anyone or anything… you’re not free, not in the absolute sense.

We all wear a form of shackles. The only thing that changes is what they’re made of — lead, steel, silver, gold, diamond.

So what do entrepreneurs mean when they say they want freedom?

The Chase That Never Ends

First, it’s freedom from a boss.
They quit the job… only to find they’re now CEO, CMO, CFO, and the intern all in one.

So they chase again.

Next, it’s a bigger lifestyle. The house, the Escalade, the landscaper. But along with it comes debt, maintenance, insurance.

So they chase again.

Then it’s passive income — enough to cover expenses without “working.”
They hit it… still nothing.

So they chase again.

Finally, it’s net worth. The big number. The goal. The “I made it.”
And when they get there? Emptiness. Sometimes depression. Guilt over the moments they missed while their heads were down. The time they’ll never get back. 

Because the problem wasn’t freedom.
And it sure wasn’t money.

Why It’s Not Happiness Either

I know some of you are thinking…obviously it’s happiness!

Hate to burst your bubble but that’s not it either. 

Happiness is an emotion. It’s not meant to be sustained. Life’s going to throw sadness, frustration, anger, jealousy at you — and it should. Without the rest, happiness loses its meaning.

The Real Thing You’re After
 

It’s peace.

ChatGPT defines peace as “a deep sense of inner calm and contentment that remains steady regardless of external circumstances… your mind settled fully in the present, your body softening, light, unshakable ease.”

Pretty good.

But here’s mine: peace is knowing you have enough — and being the person that’s capable of enjoying it.

That last part is where most people get stuck.
Because if you don’t like who you are, if you aren’t proud of who you’re becoming, then no amount of money will make you feel safe, steady, or at rest.

We think we’re working toward freedom, but often we’re just buying more distractions.
And distractions don’t heal insecurity. They don’t fix a restless mind. They don’t replace the satisfaction of looking yourself in the mirror and liking what you see.

You can build wealth without building yourself. But when you do, you’ll hit your “enough” number and still feel empty — because you never became the kind of person who can enjoy what you’ve built.

It doesn’t come from quitting your job, hitting a net worth target, or even buying back your time. It comes from doing the work on yourself, your relationships, your health.

Yes — you need your basic needs covered first. In our society, personal development is a luxury. But you don’t need millions to find peace. Just enough to live — and the wisdom to stop when enough is enough.

What It Looks Like for Me
 

Before I sat down to write this, I was on my deck talking to God.

The sun was warm. My mind wasn’t in the past or the future. I was just there.

Grateful for my wife. For parents and in-laws I love. For friends and business partners I can be myself with. For the work I’ve done over the last 4–5 years — deep conversations with people like Nick, where beliefs get challenged, values get tested, feelings sometimes get bruised but respect stays intact.

That’s where peace comes from.

I wasn’t chasing. I wasn’t running. I was smiling in the sun.

So I’ll leave you with this:
Are you chasing something… or running from someone?

Because until you know the answer, no amount of “freedom” will set you free.

As always, thanks for reading,
Kyle

Song Section for Your Newsletter

Song of the Week — “68” by Nolan Taylor
This week, press play on “68”—a raw, unfiltered performance that’s more than just a song. It’s a reminder that peace is simple. It doesn’t need polish. It just needs presence.

Let it play. Sit with it. Let the quiet resonance ground you back into yourself.