Here's an odd little ambition for you.
I wanted to make enough money that I wouldn't have to do the work I'd grown up doing.
And then, if things went according to plan...
I could go back to doing some of that very same work.
Ha.
Sounds like a fellow who could use a good long walk, doesn't it?
But stay with me. There’s a difference here that took me an embarrassingly long time to see.
I grew up on a cattle ranch in Colorado.
In that kind of world, work isn't an abstraction. It's a thing you can point to.
A fence stands where there wasn't one. Something broken works again. A job gets finished. The day has an actual shape to it.
There's something satisfying about that.
And I did other blue-collar work, too. Building fence. Construction. Jobs for clients.
Work that can be tiring, demanding, and honestly pretty enjoyable when you're in the right frame of mind.
But when you're doing it because you need the next check...
And then the next...
And the next...
The whole arrangement starts to change.
You're not just building a fence.
You're trying to keep the financial machine fed.
Which means even after a long day of doing the work, part of your mind is already worrying about where the next job is going to come from.
You finish something, and instead of enjoying the feeling of finishing it, you think about the next invoice, the next client, the next expense.
What should feel like a finish line starts to feel like a starting gun.
And then there's the other problem.
You're tired.
Too tired to want to do the next job.
But you need the next job anyway.
That's a hamster wheel with a pretty impressive work ethic.
And to be fair, it isn't unique to physical labor. People can build exactly the same trap with laptops, retainers, calendars, and very expensive office chairs.
Working for yourself doesn't automatically mean you're free.
Sometimes you've simply built yourself a job with an unusually demanding boss.
And the boss is you.
Good Lord.
So when I discovered the idea of earning a living on the internet, something clicked.
Here was a world where writing, systems, ideas, communication, and technology might let the work you did once continue to create value later.
That was enormously appealing to someone who knew what it meant to trade another long day for another check.
Of course my first experiment was a financial disaster worth $13.46.
Still, I couldn’t unsee the possibility.
And the more I thought about it, the more I realized I wasn’t fantasizing about never working again.
I was fantasizing about not having to say yes to the next job just because I needed the next check.
I imagined having enough financial independence that I could choose my work, my schedule, my projects, my days.
Not waking up already feeling behind.
Not taking a job simply because survival demanded another job.
Not constantly wondering whether there's enough energy left to keep running on the wheel.
Money mattered. It still matters.
But what I wanted money to buy was a little harder to put into words.
Choice.
Room to breathe.
The ability to do something because it interested me, not only because it paid.
And then came the realization that still makes me smile.
If I had the freedom I was looking for, I might very well go out and build a fence.
Not for a client whose check I desperately needed.
Not with that exhausted feeling that the whole point of finishing one job was to find another.
Just because I felt like building something.
Because I enjoy using my hands.
Because good physical work can be satisfying in a way that's difficult to describe to someone who has never felt it.
Because sometimes you want to end the day with something standing in the world that wasn't there in the morning.
Same fence. Same tools. Same sweat. Entirely different reason for being there.
Now, that’s interesting.
Because if the work could be exactly the same, maybe the work wasn’t what I’d been trying to escape in the first place.
It turns out you can dislike an arrangement without disliking the thing you’re doing inside it.
You can love a craft and still want out of the business model surrounding it.
You can want more money without wanting a life that revolves around money.
And you can want freedom without wanting to sit around doing nothing.
In fact, I've started to wonder if a lot of the things we call freedom are really about wanting to do meaningful things by choice.
That doesn't magically solve the bills. It doesn't make difficult work suddenly easy. It doesn't mean everybody has the same options.
But it does change what kind of life seems worth working toward.
And this is where an old story began to interest me.
You know the prodigal son? The one who leaves home, travels into a different life, and eventually returns seeing things differently?
My life isn't that parable, and I'm not trying to force it into a neat biblical ending.
But there's something compelling in the shape of it.
Sometimes you have to imagine leaving something before you can understand what you genuinely love about it.
Sometimes you go searching for an entirely different life and find that the thing you wanted most was a different relationship with the life you already knew.
And sometimes the adventure brings you back, in a strange way, to the place where you started.
I haven't arrived at some final destination. I'm still building, learning, trying things, changing my mind.
But I like where that question leads.
What would you choose to do if you didn't need to prove anything by doing it?
That’s a good question to carry around.
And it brings to mind a peculiar old story about a farmer who became convinced the life he wanted was somewhere else.
He went looking for it.
What happened back on the land he left behind is the part I can’t stop thinking about.
I'm not saying the point of financial independence is to make money and then go back to working for free. I'm saying there's an enormous difference between having to and getting to. The choice is the part I find beautiful.