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Most People Quit Their Jobs Only to Be Enslaved by a New Type of Boss

by | Oct 25, 2021 | Entrepreneurs

Right now I am a scared little man.

People think I’ve gone a bit nuts because I started a brand new Twitter account, set up a Substack, and joined Bitclout. They’re bang on.

I am scared. A lot of what I’ve built online has been centered around one platform: LinkedIn. I’ve been banned (accidentally) multiple times. When 7 years of hard work is at risk, you start to go a little bat sh*t crazy.

Recently I quit my job. That’s when it hit me. Most people trade their job for a fantasy they think is entrepreneurship, or freelancing, or a small business, or a startup, or whatever the heck you call making money online.

Maybe you’ve quit your job. Or maybe you’ve dreamt of doing it. This firsthand experience will save you from a giant pain in the ass. Let’s go.

The illusion of time freedom

I spoke to a friend recently. They quit their job in a big corporation a few years back. I imagined they must be really happy.

“It’s a nightmare. She won’t stop calling me. She wants it by Christmas.”

He now writes on various platforms and has a freelancing business. That lady is a client of his.

“She is worse than my boss. If I don’t do as she says then I can’t pay my bills. Remember: I don’t have a job. Ahhh.”

Does that sound like freedom to you? Nope. Personally, I want to sit at home in a jockstrap and watch finance documentaries. Call me crazy. Having a cranky old lady from the desert plains of outback Texas swear at me on a nice Australian afternoon feels like a death spiral into madness.

The algorithm slave life

My friend also relies on several tech platforms to run his content creation business. No matter what industry you decide to work in, you’ll face the same danger. If you’re not convinced then look at Gmail.

Did you know Gmail has an algorithm like Facebook’s that determines who does and doesn’t see your messages? Or what about the Newsbreak slave drivers? Okay, let’s not go there 🙂

At the start it’s hard to escape the algorithm captors that seek to maximize their profit, not yours. Jovan Cicmil runs an online course business.

If you rely on one platform to promote your work, then you are at the mercy of that platform’s algorithm. And let me tell you as a software developer: algorithms are fickle creatures, especially ones that use tens or hundreds of parameters.

One wayward line of code by one solitary web developer employed by the platform can ruin your entire business plan. One decision by a chief something officer can do the same.

The algorithm is like a boss. Follow its hidden rules that nobody knows. Accidentally break the algorithm dictator’s rules, and you’ll be punished. Unlike real-life where you go to a court of law and face trial, in algorithm land there’s no trial. There’s no innocent until proven guilty.

A high-fiving tech bro in a startup t-shirt with a Starbucks cappuccino in one hand and the keys to your entire life in the other hand makes a decision. They make lots of these decisions so they want your digital execution over quickly.

Most of the time they push the red button to throw you out like trash. There’s no phone number you can call to talk with them. Platforms don’t have humans that answer phones, only programmed robots in human skin that couldn’t care about your livelihood. Sell ads. Make money. Dominate the world. Do no evil (or is it do evil but don’t get caught?).

The algorithm is a modern-day boss. Some would say they’re crueler than a bad boss in a pinstripe suit with a huge ego. You decide.

The simple answer to hidden bosses that enslave us

A mentor of mine said to me once “if you can’t package it all up and sell it as a business then you’ve bought yourself a job.”

That’s what many of us do. We create something outside of our 9-5 job and then one day do it full time. It feels like a dream until we realize that if we’re sick for a few days then the whole thing can’t run without us. That’s not a business. That’s not time freedom. That’s not the life you expected to transition to.

There are three ways to quit these pain-in-the-ass bosses.

Smart diversification

I need algorithms for the time being. Because I can’t trust any of them to serve me like a loyal human, I cheat on them with multiple algorithm girlfriends. That way if one of them dumps me then I’ve got a new one to love.

Find a second algorithm until you’re established enough not to need them.

The breaker of slave chains

Financial assets aren’t bosses. Although if you become a landlord then you’ll meet the other type of boss: tenants.

The way you avoid digital enslavement is to make money and buy financial assets. Over time they grow and help you to care less about what XYZ tech platform is doing, or what your client’s next book they want you to write will be about.

Financial assets help you say “screw that” to yourself, quietly.

The hidden enhancer of time

Twitter has been a big part of my diversification. It’s an old app many people don’t get. I’ve seen multiple firsthand creators build 6-figure passive income streams on the platform.

Their strategies are so stupidly simple it should be criminal. I’m not going back to Twitter with a brand new account for the money, though. I’m going there because I love Twitter Threads.

Passive income is the ultimate way to avoid these new forms of horrible bosses and enhance how much free time you have. Passive income is the easiest to generate on the internet. Here are some examples:

  • Online courses
  • Affiliate links
  • Membership communities
  • Paid newsletters (Substack)
  • eBooks
  • Paid templates
  • Cheatsheets to popular apps like Notion
  • Youtube videos with ads
  • A website that generates traffic that can be monetized in lots of ways

Move away from bosses with passive income. Then you can say “thanks but no thanks matey.”


The key isn’t to never use a tech platform with an algorithm or to avoid every client. No. The key is to be aware of how algorithms and clients can become a type of boss if you don’t pay attention.

A millionaire Youtuber who only gets paid by Youtube is an employee, not a person who has all the free time in the world and can do whatever they want. This point is often missed.

Don’t trade a 9-5 boss for clients or the algorithm equivalent. Oh, and don’t trade your life in to become a debt slave to a bank either if you can avoid it.

What do I suggest? Have a website you own as well as multiple algorithms that expose your work to new people. Replace clients over time with passive income from digital products and services. That way, you can say no to clients or only work with the ones that treat you like a sweetheart.

Then when you’re successful enough, follow the path of some of my favorites — like Ryan Holiday, Mark Manson, Tim Ferriss — and divert everybody to a website you own and control. That’s how you don’t trade one boss for another, and buy back your time to explore your true creativity.

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