Not subscribed?

Get the “Pursuit of Freedom” letter every Wednesday for short lessons on business, freedom and self-mastery.

Freelancing: The First Step to Complete Freedom

You’re not the only one to feel stuck in a life that you can’t stand. You won’t be the only one to quit that life and pursue your own path either. Fortunately, thousands of others have turned their back on the traditional path of going to college, getting a job and retiring after four decades of work.

Unfortunately, people born between 1990 and 2005 seem to be among the most indoctrinated to believe that freelancing is too risky, and the traditional path is the only safe path. Myself included.

A Victim of Helicopter Parenting

Like thousands of others born in the late 90s, I was subjected to the kind-hearted but misguided parenting strategies of fearful parents. Fear campaigns were launched every week against everything from MSG in food to kidnappers prowling the streets in search of inadequately protected children.

Hundreds of thousands of young parents heard these horror stories (many of which had been egregiously blown out of proportion), and decided to adjust their parenting to compensate.

Their kids grew up in the world that resulted. A world of helmets, hovering and constant suspicion. The fast-evolving Karens roamed the landscape looking for any conceivable threat to their children. Many fun things were screamed off the stage, but this unfortunate truth is nothing compared to the realproblem.

The real problem, is that, having nothing to compare our life experience to, many of us grew up feeling that this culture of helicopter parenting was normal.

We were suspicious of people that we didn’t know. Afraid of chemicals we believed hid in our food waiting to poison us. Mistrustful of doctors. Skeptical of anything that wasn’t already familiar and known to be safe.

As a result, an entire generation of victims was introduced to the world.

Fortunately for me, my parents divorced when I was in my early teens. I moved to a different town with my father, who was a busy professional. He spent hours every day working, and more hours every weekend band gigging at local bars.

For the first time in my life, I was blessed with a striking degree of personal freedom. I no longer had parents hovering over my shoulder on a daily basis, examining and questioning every decision I made (or making them for me entirely). It was frightening at first, but I soon found the experience magical.

I stayed out late with my friends every night. I spray painted buildings, drag raced my 1994 Subaru Legacy and did drugs for a while. But I quickly found that these illicit thrills weren’t really for me, so I set out to find what WAS for me.

Then, I discovered money.

Money = Freedom

If you’re reading this, you and I are probably a lot alike. You probably realized in your late teens or early twenties that you want money. LOTS of money.

More importantly, you want what money buys: freedom.

I was just out of high school when I found out that, holy SHIT, did I want freedom.

  • I wanted to have so much money in my bank account that I didn’t have to worry about how I was going to pay my rent
  • I wanted to have a nice place to live
  • I wanted a red late-model Acura NSX
  • I wanted fun toys to play with. Motorcycles, cameras, computers, guns, boats, airplanes, you name it
  • I wanted to be able to travel the world and explore it on my own terms

More importantly, however, I discovered what I didn’t want.

I didn’t want a job where I’d have to work with a bunch of… well, people who didn’t share my values. I didn’t want a boss that made my eye twitch every time he asked me to do something stupid. I didn’t want to have to wear a uniform.

I didn’t want anyone to tell me:

  • What to do
  • When to do it
  • How to dress
  • What to say
  • How to behave


I didn’t want to be controlled.

But at 18, I’d been controlled my entire life. I had absolutely no idea how to get to the point where nobody could control me.

I spent a couple of years trying like hell to figure it out. I sold cars on commission for a Nissan dealership, and again later for a Chrysler/Jeep/Dodge dealership. I tried to be a freelance photographer, first doing portraits and later trying to freelance for the local newspaper. I tried my hand at food delivery, Uber, network marketing. Basically every gig and get-rich-quick scheme I could find.

Nothing worked.

Everything that offered me freedom offered me very little money. Everything that offered me decent money provided less freedom. Everything that offered me money AND freedom required skills that I just didn’t have.

The closest I ever came was commissioned sales, but that was just not something I was capable of at the time.

When I was 20, I had washed out of my latest job selling cars. I just couldn’t figure out how to make people trust me enough to buy from me. People didn’t seem to like me, and I was so tired of trying. The rejection and humiliation had gotten to me.

I quit my job and went home to my empty three bedroom apartment. Both of my roommates had left, and I was alone in a huge apartment. I felt small and isolated, and collapsed face-down on my bed, hoping that someone would break in and murder me. In that moment, I knew for a fact that nothing I tried would ever work, and that I might as well give up.

My Big Discovery

I would love to tell you that something finally clicked that day and everything thereafter was smooth sailing. What happened that day is a story for another day, but I will tell you that everything did change.

But it wasn’t smooth sailing by any interpretation.

I’m 26 now. I’ve been a freelance web developer for the last four years. I still have months where I have to be a little more financially conservative than I’d like. I still face difficult challenges on a weekly basis. I still don’t drive a new Acura NSX.

But here’s where I’m at:

  • I have a safe, reliable vehicle (Alice the Tacoma)
  • I have a comfortable apartment in a safe neighborhood
  • My fridge is always stocked with healthy food
  • I’m able to spend time and money learning new leisure skills
  • I only need to work ~15 hours a week

More importantly:

  • Nobody tells me when to work
  • Nobody tells me where to work or when to be there
  • Nobody tells me how to dress
  • Nobody tells me what to say, how to dress, or how to carry myself
  • And if they do, I get to fire them.

I’m not rich by any stretch of the imagination (yet). But I am completely in control of how I spend my time, who I work for, the kind of projects I take, and where I live.

If I want to, I can pick up and go work somewhere else for as long as I want. And I’m not talking about across town, either.

  • In 2019, I lived and worked remotely in the US Virgin Islands
  • In 2020, I spent half the year living in Portland, Oregon
  • In 2021, I spent half the year living in San Diego, California
  • This winter, I’ll be spending a few months in Panama City, Panama

And I’ll still be able to take new projects, do my best work and improve my future.

I’m not a millionaire yet, but I’m free, and damn, am I happy.

The best part? It’s completely possible for you too.

I’ve boiled the transition to freelancing down into a simple process

Becoming a freelancer is simpler than you might think. I got started as a web developer with very little initial skills. Want proof? Here’s a screenshot of my very first website that I sold for $600.

A screenshot of my first ever website.

Becoming a freelancer was simple, but it definitely wasn’t easy. At least not the way I did it. I quit my job, burned all my ships and gave myself no path except “forward.” There was no retreat.

But if you already have a job, I’d recommend keeping it. Transitioning to freelancing is something you can do in just a couple of hours a day (although spending more time will obviously get it done faster). And unless you’re like me—dependent on a certain degree of anxiety to propel you into furious action—you might be better off with a safety net.

The first step is identifying the service you’ll offer, which I’ll cover in the next article. This will be the vehicle that you use to get you to your destination. Perhaps you already know which service you want to offer, in which case you’ll learn exactly how to position it, who to target it at, and how to get really good at it.

If you don’t know which service to offer, you’ll learn to identify a market to serve, identify a problem to solve, and learn how to solve that problem in a way that plays to your strengths.

Every sturdy home starts with a rock-solid foundation, and this is your key to building it. Stay tuned!

I'm John Kakuk.

I’m a brand designer, web developer and marketer working with architects, engineers and construction companies. My purpose is to help others achieve the best versions of their businesses and themselves.

Here's how I can help you: