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Why Society Doesn’t Want You to Succeed (and What to do About it)

You’ve heard a chest-thumping guru or two say something along the lines of “everyone is just trying to hold you down!”

They’re right, but this way of thinking goes much deeper than that platitude. In more ways than one, society is actually designed for you to be average. And this isn’t some evil conspiracy to keep you down. There are actual tangible, pragmatic, and even financial reasons for them to want to do this.

When you understand the chess board, you can navigate it. Just accept the idea that society has incentives to keep you from improving as fact, get over it, and move forward with a proper understanding of how the world works.

So what the hell am I talking about?

How We Organize Societies

“Civilized man has exchanged some part of his chances of happiness for a measure of security.” — Sigmund Freud

Let’s say we had a laissez-faire system where everyone was encouraged to be unique individuals who all followed their highest pursuits. Society wouldn’t function correctly. In very pragmatic terms, you need A, B, C, and D players to keep the wheels spinning correctly.

Keep in mind, I’m not a historian or anything like that, so don’t pick into the details of the synopsis — the sentiment is what counts, okay? After the manufacturing boom, you needed a lot of people to work in manufacturing.

So we filed people into the factories. But then, someone needed to watch the kids.

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Not only did someone need to watch the kids, but we also needed to train the next generation to be complacent so they, too, could become factory workers.

Then, corporatism and consumerism got into the mix at the same time. Now, society really needed you to fit in because fitting in meant you would buy more stuff you didn’t need.

Then you have the role of employers. In a very real sense, employers need to create a situation with a lot of downsides for you to keep you compliant.

Nassim Taleb explains this well in an excerpt from his book Skin in the Game, specifically an essay titled How to Legally Own Another Person:

“In short, every organization wants a certain number of people associated with it to be deprived of a certain share of their freedom. How do you own these people? First, by conditioning and psychological manipulation; second by tweaking them to have some skin in the game[…]”

He goes on to say:

“Someone who has been employed for a while is giving you the evidence of submission

Evidence of submission is displayed by having gone through years of the ritual of depriving himself of his personal freedom for nine hours every day, punctual arrival at an office, denying himself his own schedule, and not having beaten up anyone. You have an obedient, housebroken dog.

Employees are more risk-averse, they fear being fired more than contractors do being sued.”

His tongue is a little sharp for my taste, but he does hit the right nerve here. I can’t tell you how many times I’ve heard someone tell me they would follow a dream but they have to pay their bills, pay off their debt, keep their health insurance, etc.

Do you think the system was designed with this many strings tied to you on accident? There’s no Illuminati. Don’t picture Homer Simpson attending the Stone Cutters meeting.

But societies emerge to become more and more restrictive because they have to. We live in a “free country” and you have “free will” but not really. Not when the game is rigged like that. And make no mistake about it, if you want to find freedom it’s going to be difficult. Especially when you have more than just the powers that be to deal with.

Your Friends and Family Kind of Suck (I’m Sorry)

Try an experiment for me. Over the next week, tell a bunch of family and friends you’re going to take your savings and start a restaurant (or literally any other business for that matter).

Pay careful attention to what they say and how they say it. They’re not going to outright tell you not to do it (well, some will). Instead, they’ll ‘concern troll’ you.

“Gee, I don’t know Bob. I heard most new restaurants fail.”

“You’re going to spend all your savings? Is that practical?”

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There are a few exceptions. My grandmother-in-law let her husband open up a restaurant even though she didn’t think it would work. She wanted to give him a chance to try, though. It didn’t work out, but they didn’t die either. They recovered. And at least my grandfather in law gets to say he tried. And that’s worth something — much more than you know.

Anyway, it’s not that your friends don’t want you to succeed. It’s that they don’t want you to succeed but don’t really know they don’t want you to succeed. It’s at a deep subconscious level that’s based on a lot of different factors.

On top of our genetic wiring to envy others more successful than us, we have to deal with the, for lack of a better word, conditioning we’ve had to endure from society (more on that later).

And no, this isn’t me calling other people “sheeple” or claiming that anyone is really out to get you. None of this is malicious. It just is. Again, it’s not concocted either. It’s just how things naturally came about.

Human beings are status comparing machines. Social dynamics are a big part of evolution. Your pecking order in the tribe had real consequences. So, deep down, when those around you see that you’re starting to improve, it tickles their lizard brain sending a subtle message that someone has definitively risen up the totem pole.

So, they will try to tear you down to make themselves feel better without even really meaning to. Don’t blame them. Treat it like a physiological trait, because it kind of is. Deal with it. Treat it as fact. This is the motto that saves your sanity.

The Media Wants You to be Depressed, Sad, and Angry (Because it Helps Them Make Money)

Charlie Munger, one of the smartest people in the world, has a quote that permanently stuck with me since I first read it:

“Never, ever, think about something else when you should be thinking about the power of incentives.”

Munger often says if you know the incentive, you know the outcome.

Let’s take a look at the different ingredients in the “incentive recipe” for the media:

  • Media companies (especially news companies) need eyeballs. They sell this attention to advertisers.
  • Studies have shown that high arousal emotions, particularly negative ones, drive the most engagement
  • Companies need to make money

I used to get upset with the media for trying to gaslight me until I realize…they have no other choice. Reflecting life, society, and the world accurately would cost them (lots of) money.

Nassim Taleb has a saying, “To cure yourself of the news, read last weeks news.” It’s all a giant heaping pile of bullshit. Again, it’s not malicious, per se, it’s just the obvious outcome of a perverse incentive structure.

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And I just touched on media companies like news websites. Social media is the 300-pound gorilla of psychological engineering. I’m just as hooked as you and I don’t have a great solution for this other than try to get smarter and somewhat curb your social media use. It’s hard.

These companies employ not just a few, but thousands of the world’s smartest people — psychologists, engineers, programmers, etc — for the sole purpose of trying to figure out how to make social media more addictive. It makes sense. All the incentives point there.

Make no mistake about it. You are being gaslighted on a daily basis. Knowing that doesn’t necessarily make you immune to deception, but you’ll start taking what you read, hear, and see with a massive grain of salt. Again from Taleb, “Trust none of what you hear, half of what you see, and some of what you read.”

If I haven’t hammered my point yet. Let’s try a thought experiment.

The population of the United States is 325 million people. Say I was a news company and I wanted to fear monger about “disease x.” I could air a segment about a new case of disease x every single day for a full calendar year and make the public petrified. And if there were only 365 total cases — .0001% of the population — I could make a rare disease look like an epidemic.

Now, this is rough math, obviously, but you get the point. The media cherry picks stories and narratives. It’s not so much what they tell you as much as it’s what they don’t tell you. Again, no grand conspiracy. Just simple incentives.

Make No Mistake About it, You’re Fighting an Uphill Battle

The whole point of this segment is to let you know that I understand how hard it is to just “lift yourself up by the bootstraps,” because society doesn’t want you to — at least not all of us at once.

That leaves you. The only fighting chance you have comes through personal responsibility and self-reliance, with the full understanding that you have to have an above average skill level to play a rigged game.

The good news, though, is once you understand the game is rigged, you don’t play it. You play by your own rules and actually follow them, which dramatically increases your odds of “escaping the Matrix”


This is a test section for a new book I’m working on. Tentative title Real Help: A B.S. Free Guide to Self-Improvement. I’d love your feedback. I’m trying to test out ideas like a comedian at an open mic night.