The Challenge of Freedom

It wasn’t long ago that I was working a 40-hour a week job that I truly hated.

I was not a good employee. I never have been. The days would slip away, and the only thing that grew was my resentment.

Is this good for the company

In my last job, I did have autonomy, though. As long as I was getting my work done, I was free to budget my time as I saw fit.

So I developed a system. It wasn’t uncommon for me to buckle down and hammer out a week’s worth of work in eight hours so I could spend the other 32 on writing and developing a side hustle.

In time, my priorities shifted, and I cared less and less about my actual job. I would get irritated when my private enterprises were interrupted by an e-mail or a request for a progress update. My work for the company started to get sloppy, my attitude soured, and I started to gain some unwanted attention from my supervisors.

There was no turning back. I could no longer place myself back in the mindset of a person giving 100% effort to my employer. Even giving 20% of my effort was asking too much. I saw my future with the company. More responsibility. A heavier work load. 60 hours a week. And for what? A couple hundred more dollars every two weeks?

It wasn’t worth it to me.

In November, a mutual decision was made and we parted ways for good. I was out.

But I made a mistake during this critical period. Instead of taking a full measure, I took a half measure. 


I ran into a friend just after I had gathered the last of my possessions from my old office. He owned a small cafe not far from my house, and offered me a casual part-time position. “This is just what I need” I thought to myself. “Zero responsibility or frustration. Easy idiot work. Yes, it’s a job, and I swore I’d never take one again, but having a safety net won’t hurt”.

What ended up happening?

I started giving him more and more hours. It changed from a casual gig to a fairly significant commitment. 

In short, it turned into something it was never intended to be: a major time commitment.


A month ago, I told my friend I was leaving for good when I took a week off to visit the beach.

Let me tell you, it takes a leap of faith to turn down fast money in exchange for time (playing the long game).


The week at the beach was meant to be endlessly productive. To be a catalyst in this process.

In truth, it wasn’t.

Much like Dylan over at Way of the Olympian, I lounged on the beach and slept too much. When I got back home, the pattern continued. I was laying on the couch, eating Chipotle, and straying from the path I had laid out for myself.

“Oh fuck. I’m going to have to get a job.”

This is the challenge of freedom. The voice of self-doubt that whispers “This is hard. You’re going to fail. Wouldn’t it just be so much easier to save yourself the frustration, give up now, and be a slave again?”

I’ve conditioned myself to associate these thoughts with experiences from my past. Namely the miserable jobs I have worked at, and the miserable people I have worked for.

I’ll illustrate one example:

For years, I developed and ran a business, a division of a larger company. I poured my blood, sweat and tears into the design, the builds, the marketing and the maintenance of that place. I “owned” it. But when push came to shove, I still worked FOR the parent company. I was simply an employee. When I left, it was not with my head held high, but defeated, empty-handed and broken.

Four years later, I have nothing to show for that effort. My name was immediately struck from the record, as though I never existed. The business has stagnated and failed to build upon my work, but this division of the company has nonetheless continued to turn a significant yearly profit directly due to my time spent there.

Others are reaping what I had sown.

I had built something wonderful. It was something I was proud of, something that was truly heart and soul. But I had built it for someone else. When I became a problem employee,  one who was too much of a liability to upper management, the solution was obvious to them: I was violently pushed out and erased.

This is my motivation: I will never allow this to be done to me again.

Everything I am building, I own 100% of it. There is no one else to strategically force me out. There is no one to disagree with, no one to look over my shoulder to check on my progress. There is no one to answer to but myself. 

When I succeed, I will have no one else to thank, but if I should fail (I won’t), that burden falls squarely on my shoulders.

 

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