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A Side Hustle Has Nothing to Do with Quitting Your Job and Looking Cool

by | Aug 29, 2022 | Entrepreneurs

The side hustle genre is a low-budget horror movie.

Most of the advice is bad, or impractical at best. And many of the people writing about this topic have no clue. I had a side hustle for 7 years while working many pain-in-the-ass jobs. Side hustles aren’t what they seem.

Let me light the internet on fire and explain side hustles properly.

Side hustles got popular during an unusual time

The first time I noticed side hustles had become popular was when a smart tweet stated that the former Donald Duck President treated the job like his side hustle. The tweet blew up.

This was right before the March 2020 bat virus. Once the great reckoning struck and everything closed, people’s attitudes towards work and making money changed.

The idea of an income would never be the same again.

Around the same time people took the word “hustle” from the phrase side hustle and got drunk on it. Every time I mentioned side hustles a few randoms got upset and triggered by the phrase.

They thought side hustle meant working yourself into the ground until you burn out and die in front of your computer screen. Nope.

The true meaning of side hustles that most people don’t know

Side hustles are popular because they’re part of the new permissionless economy. With side hustles, you no longer have to ask for help.

  • You don’t need to do job interviews.
  • You don’t need to fake-flex in a resume.
  • You don’t need to be chosen by a book publisher.
  • You don’t need to get discovered by a record label.
  • You don’t need to wait for a promotion or hope to get a pay rise.

A side hustle means to execute now and never ask for permission later.

Now you can see why it became popular. Younger generations are sick of asking for permission or being held back by forced inequality built into the societal system they participate in.

Some cry or beg for more money.

Side hustles are about taking ownership for your future and putting the work in. We can cry the system is broken and hope the political grandpas who get rich off it change their ways.

Or we can work after hours and build new online empires.

The pornification of side hustles

Those who promote side hustles have lost the plot.

Side hustles have become all about looking cool. On the little birdy social media app, side hustles have become about talking down to others.

“Have fun staying poor” is a common line from these silly hustlers.

Then there’s the overdone narrative that unless you use a side hustle to quit a job, you’ll never be successful in life.

Look, I’m the first person to hate traditional jobs. But it doesn’t mean everyone has to quit their jobs. I was happy for years doing a job and working on my side hustle after hours.

Then it got to a point where I wanted to work for myself.

That was a personal choice and it was right for me. Keeping in mind I had a startup in my 20s so the whole online business thing wasn’t brand new to me.

My problem with the pornification of side hustles is it deters people who desperately need one from getting started.

They think it’s a success catwalk show where they have to become some silly little influencer.

That’s not what side hustles are at all.

Everyone needs a side hustle for this underrated reason

A side hustle works best when thought of like this…

It’s a backup plan.

  • Maybe your employer fires you.
  • Maybe the recession chokes the last few dollars out of your bank account.
  • Maybe you figure out, finally, that your boss doesn’t give a crap about you.
  • Maybe a bat virus version 2.0 gets unleashed on the world (ya know, like the seven plagues fairytale).

Or maybe one day you wake up and realize you hate your life.

That’s when a side hustle has enormous value. A side hustle is Project You which can save the day (or your life) when sh*t hits the fan.

This is how average people can start successful side hustles

I don’t talk about side hustles for trust fund babies or millionaire tech bros.

I have no clue about their way of life. All I have experience in is going from an average person with a side hustle, to making a side hustle my full-time work. I didn’t do it fast either. Took me years.

But I’m not that smart.

You can probably do it faster if you adopt these ideas that took me years to work out.

Get real about risk amigo

A side hustle requires some risk.

The truth is most people won’t even invest in a $97 course that can teach them a new skill. They get stuck in decision mode or trying to lower the downsides.

Side hustles work when you think of them as small bets.

You try a few things on the side and see what sticks. And you understand that no one small bet will be enough to destroy your time or bankrupt you.

No risk it, no biscuit.

The Einstein philosophy to level up

Einstein wasn’t the sexiest dude alive. But the guy loved to run experiments and test his theories. Side hustles are no different.

Photo by Taton Moïse on Unsplash

The fastest way to kill side hustles is with:

  • Expectations
  • Perfectionism
  • Procrastination
  • Lack of patience

Experimental thinking helps defeat these demons. When you expect things to screw up and blow in your face, the ability to keep going is within reach.

If all you do though is curse at every tiny mistake, it’s unlikely your side hustle will ever have enough oxygen to breathe new life into your work-life.

When things go wrong it’s awesome. That’s how you figure out what works.


Most side hustles start out as learning.

If you have a desire to learn something new then that’s the side hustle disease in disguise. Get infected. Go on Youtube and learn for free, first. Then take what you learn and put it into action online.

Test. Learn. Iterate.

This 3-step process became famous in startup land. It applies to side hustles too. Follow your curiosity.

Own instead of rent

Many things in life are rented. Yet the illusion is we own them.

Take social media accounts for example. You don’t own any of them. You rent them off madmen like Mark Zuckerberg who spy on you while you’re in your underwear rubbing one out after a hard day at work.

The illusion creates rent-to-own.

The reality is many things online can never truly be owned. Sending emails is a great example. Yes, if you build an email list with your side hustle, then you own it.

But Gmail can easily block your emails too if they like. Just pop Joe Rogan or Elon Musk in the subject line and you’ll see what I mean. Or jump on Youtube and mention the red flag country that hosted the Olympics in 2008.

The lesson here is simple: make sure you blend Web3 with your side hustle — where side hustlers will own their work, the services they use, the apps they create, and the audiences they build.

The most important side hustle tip that’s not obvious

Let’s finish here.

Successful side hustles are tied to an obsession, not passion. Passion is lukewarm. It’s an orgasm that comes and goes.

Obsession leads you to marry your side hustle.

For me, it’s impossible not to do my side hustle of writing online full-time. I can’t breathe without her. I’m in love every day. It’s an unhealthy obsession. It’s a coke addiction.

Making time doesn’t exist. I do my side hustle before I consider doing anything else. It’s always been like that.

The number one sign a side hustle is meant to be in your life is you’re obsessed. It has nothing to do with quitting your job or looking cool.

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