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If You Fit In, You’re *Not* Free

by | May 29, 2023 | Financial Freedom, Money

The bullies from my high school still abuse me.

Yet I’m a grown man. It feels kind of weird. I always figured one day they’d be married, get a mortgage, and have kids so they wouldn’t have time to worry about me. But they still do.

Everything I do online is a joke to them. They love to leave messages on my social media posts. They say my charitable acts are fake.

When I bump into these bullies out in public they give me hell. They just laugh at me. “You’re a joke Denning.” Many times they’ve wanted to kick my head in but I leave before they get a chance.

I never fit in at school.

I was weird. I didn’t watch the same movies as them. I didn’t train for a career or do my math homework. When the cool kids ran away from me at school and I had no one to play with, I got depressed.

So I made friends with the most dangerous people I could outside of school. They did drugs. They carried knives. And they treated me like their little brother.

It gave me a massive sense of significance, such is violence. I don’t talk to any of them anymore because they’re all in jail.

Because school friends were hard to keep, I had to become an expert at networking to make up for my shortcomings.

This led me down all sorts of strange paths. From working at a strip club as a DJ, to driving Limos full of famous people, to starting random businesses, to writing online full-time.

I now look at the school bullies and see their life as a prison. They fit in but they have no lives. They live for the weekends, they hate their jobs, they troll people, they never have enough money to go anywhere.

Live is one big struggle.

And they think I’m the loser. The truth is I feel sorry for them. When you fit in it’s the fastest way to be trapped by the tragedy of modern life.

The greatest prison of all

Our thoughts can either free us or enslave us.

That’s why I’m obsessed with psychology. If you let false thoughts run your life, they’ll keep lying to you and destroying opportunities.

The best way to see thoughts clearly is by writing them down.

It’s why I have an online writing habit. One, to help people. But two, to see the clarity of my thoughts and see any potential prisons forming around my head. Some prefer private reflection with a journal which is fine too.

The scary part about our thoughts is they are often inherited from those around us. It’s why I’ve never hung around with people who fit in. I worry they will convince me that my negative thoughts are true.

Guard the door of your mind with an ax.

If you fit in, you get told what to do

I don’t know about you but I’m sick of being told what to do.

Those who fit in succumb to the powers above them. They believe the mainstream media or politicians have their back so they listen and comply.

They can tell you everything about some random war that’s not happening in their own country. But they know nothing about psychology, history, or what they truly want in life.

There comes a point where it’s good to live a life where you set the rules. Where you guide yourself instead of an off the shelf career plan that leads to minimal upside and long hours stuck in an office of broken dreams.

Adult babies get told what to do. Society changes their poo-stained diaper. Don’t let that be you.

The more neatly you fit into society, the less free you actually are — Naval Ravikant

Stay the hell away from the corporate drone syndrome

I was a corporate puppet for 10+ years.

Everything I said sounded like a press release. I had to watch what I say. I always had to network well in case I got laid off. I’d suck up to every corporate ass to see what I could get out of them.



Good performance review?

Corporate drone conversations are soulless. These lifeless zombies sound that way because their entire career plan is to ascend the corporate ladder and pick up a few fancy job titles along the way.

One of my fancy titles was “Global Director of eCommerce and Advisory, International Banking.” What a freaking wank. It didn’t mean anything. I took a few phone calls and sent some nice emails.

A job title is never a good substitute for actually doing interesting things in life that strangers quickly become interested in.

Here are some signs you might have become an imprisoned corporate drone:

  • You put more emphasis on gender pronouns than is needed.
  • You write “opinions are my own” in your LinkedIn bio — It’s stating the obvious. That line ain’t gonna save you if a boss or leader has a problem with your posts. The good news is your LinkedIn profile is owned by you. So ignore anyone who has an issue.
  • Your dating profile says “I like travel, food, wine, and the outdoors” — No sh*t. These are things all people like. You’ve gotta get more creative than that if you want to escape mediocrity and live the good life.
  • Your LinkedIn profile says “ex-Google, Microsoft, Uber” as if you’re a superior human being.
  • You care about other people’s opinions and live and die by them — Corporate life teaches us to obsess over feedback. But a lot of feedback at work is B.S. and full of bias or hidden incentives.

What it’s like to be unemployable

Ain’t nobody gonna hire me ever again.

Have you seen how many F-bombs I’ve dropped online? Oopsie. Sorry future boss. There’s something freeing about it. I will never fit in again. Every dinner party I go to is going to be weird from now on.

People will ask what I do and I’ll have to make stuff up. Before I’d just say “banker” and instantly fit in. As Naval says:

A taste of freedom can make you unemployable.

Once the job world has taught you enough and given you some cash to bankroll your future, it’s time to break free.

Otherwise you become trapped like I was.

Being unemployable is both scary and life-changing. It forces you to take responsibility and not blame others for your failures.

It’s just you against the world.

Work hard to buy things that keep you working?

The biggest clown show of all is consumerism.

Buying useless crap is how you fit in. It’s also how you piss your annual income down the toilet and never make enough money to invest in assets that generate passive income and set you free.

Buying less stuff is such a life hack.

I’m wearing the same pair of pants I’ve had for the last 5 years. I wear the same few unbranded t-shirts repeatedly. I own an old car that doesn’t look flashy and draws zero attention.

If I have a lunch with my former work colleagues I take the train. They all drive their BMWs and Mercs and park them out front.

I walk in with no car keys to put on the table, Nike Air shoes from 3 years ago, a black backpack I stole from my last job, and an old pair of sunglasses that my daughter scratched the crap out of.

When your material desires are zero the level of freedom is hard to describe. You become unrecognizable.

People think you got cheap. Instead, you got free.

Society tames the wolf into a dog. And man is the most domesticated animal of all — Nietzsche

Don’t rebel against mediocrity. Do this instead…

Stage a silent protest.

Live your life how you want and explain it to no one. Disappear for 6 months. Live in solitude. Work in the dark hours. Travel the world without putting it on Instagram.

Find more weirdos who do the same. Swap ideas. Stop trading time for money. Master the money game to unlock the next level in the life game.

Dare to be different. Screw being normal. And let the bullies, bully.

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