WHY I DREAD WEARING SUITS

Last year, I worked as a machine operator for a leather and shoe manufacturing company. During that time, there was a man who frequently wore suits to work. He was in his mid-forties, clean-shaven, and had a protruding belly that seemed to command instant respect from someone like me, fresh out of university.

Let’s call him Jackson.

Official attire wasn’t mandatory, but Jack chose to wear suits and a sharp pair of shoes that complemented his outfits, making him look like a member of the management team.

Heads up: he wasn’t!

More often than not, I’d joke with him about it, and Jack, ever the official-looking man, would giggle and move on with his day.

Then came the fateful day when Jack suggested I consider purchasing a pair of formal clothes and shoes that we were already manufacturing.

"What for?" I asked, genuinely curious.

"You know, you need to look presentable—like me," he replied.

"But I look presentable in my casual outfit. And who am I even trying to impress, Jack?"

What he said to me struck a nerve.

This moment marked my vow to never wear formal clothing. Okay, I know I shouldn’t say “never,” but you get the gist. Here’s what he said in my second language, Swahili—paraphrased:

"So that you can look presentable in case you decide to get a better job for yourself. Otherwise, the employer won't hire you."

“Seriously? The employer won’t hire me?” I cringed.

To me, that sounded silly and stemmed from ignorance for two reasons:

1. BEST EMPLOYERS HIRE FOR URGENCY, NOT LOOKS.

I’ve never struggled to impress an employer. In the various places I’ve worked, I’ve always received a promotion in less than four months.

For instance, I was promoted from a supermarket attendant to a supervisor in less than a month. While working with Jack, I was promoted from a casual worker to a machine operator, receiving a 33% salary increase in under four months. Heck, I’ve even been promoted to a managerial position at my current job as a high school science teacher.

You can call this luck, but I call it urgency.

Hint: employers are always looking for highly urgent individuals—those who don’t need to be followed around to do their work. They seek creative and innovative individuals who can handle high-stress environments, take full accountability for their actions, lead others without being given explicit authority (a bonus if you’re a natural at this—I know I am), and those who are time-conscious and reliable.

2. MY HATE FOR BORING WORK.

Perhaps the most crucial part of this story is my inability to tolerate monotonous work.

I love creative pursuits, and being a machine operator definitely wasn’t fulfilling that passion. It was enjoyable at first as I learned the ropes, but as with many things in life, it became boring once the novelty wore off.

Jack, on the other hand, never understood what it meant to seek creative fulfillment, and I saw little point in explaining it to him. To him, a successful life meant getting a job, starting a family, owning a nice home, and retiring at 65 to finally enjoy freedom.

Oh, and remember when I mentioned Jack was in his mid-forties? I wasn’t joking.

What does that mean?

It implies that Jack has spent most of his life believing that obtaining a stable job is the only way to live a fulfilling life. He was making a considerable effort to stick to that belief, which, for him, was the truth. It would have taken me months, if not years, to try to re-educate him about alternative paths. If you’ve read *The Alchemist* by Paulo Coelho, there’s a moment when Santiago has the chance to tell the baker about his dreams, but he hesitates. If you know the book, you’ll understand the parallel.

I didn’t want to put Jack in that kind of situation.

The reality is...

There’s a conventional path that dictates how one should live and work—like wearing suits and commuting five days a week for 40 years. Then there’s the alternative path, known as the road less traveled, which I believe offers greater rewards and the chance to live life on one’s own terms.

I don’t know about you, but I definitely don’t want to wear suits to work for someone else for 40 years in a job I despise.

I want to wear shorts, crocs, and a vest, sit at my desk, type on my laptop for a few hours, and make a good income, using the rest of my day as I please.

Does that sound too good to be true?

Maybe. Maybe not!

From my experience, I haven't even hit the $10,000/month milestone yet. In fact, I haven't monetized my skills online, yet. But I know it’s possible. I’ve seen creators achieve that in a year, which is why I’ve set a goal for 2025 to make $10,000/month through copywriting and building a personal brand.

The Internet has massively broadened the possible space of careers. Most people haven't figured this out yet. -- Naval

Now, this letter is already getting too long, and I hope I have managed to convince you why I don't like suits. Or even better, why I am against the conventional path.

If not, ask yourself the following questions;

1. Do I really enjoy my work?

2. Is there a better alternative?

2. Is it possible to work less remotely?

Take your time and answer them with brutal honesty.

Remember,

It all starts with curiosity...

Then passion, then purpose, then autonomy and finally, mastery -- in that order. Don't rush!

Hope that helps.

Talk soon,

Dennis