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Four Side Hustle Skills No ‘Guru’ Taught Me

by | Oct 25, 2021 | Startups

Gurus are full of sh*t.

None of these making-money-online gods taught me a thing. Mind you, I’m not the smartest guy. I only learn from experience. The same probably applies to you. A side hustle that levels up your life has to be experienced to be understood.

All the online courses and blog posts in the world can’t replace a good ol’ slapping across the face that comes from realizing there are very few rainbows and unicorns in this style of work.

These are the skills you must have.

Working without a boss sounds like a dream

Gurus sell us the no-9-5 dream. Mostly it’s hyperbole. When I quit my job I imagined sitting in Starbucks cafes and doing morning yoga right after a green smoothie. The dream lasted about a week.

I quickly realized without a boss there is zero urgency to do anything. And if you’ve done okay financially and have savings, then the urge to work is non-existent.

Without a stick poking you in the back it’s easy to get lazy. I found that even before I quit my job and had a side hustle, my 9-5 work got done but my side hustle work could be a real struggle.

The first skill you need is to become your own manager. That requires accountability. I had to have weekly goals to have any form of direction. What stops you from becoming a Netflix slob is sharing those goals with a person you look up to. I shared mine with my partner. She asked me every day how each goal was going.

There’s one issue with goals, though: We often have too many. My goal list at the start was far too long. So I trimmed it back to one goal per day. Any other tasks that got done were a bonus.

Most people need third-party inputs

Traditional employers have robbed us of one of the greatest gifts in the world: how to think for ourselves.

All day at work I was programmed how to think. I picked up corporate slang and buzzwords from every person I worked with. Back-to-back meetings often involved lots of Powerpoint decks reinforcing the programming. My employer told us “we are great and we’re changing the world.”

Not really. Our value had eroded over time. We took our customers for granted and treated them like a line item in the black hole of a spreadsheet. Outside of company programming there was industry programming.

Software companies would host zoom calls every day and tell us how great their product was. They’d pretend they “do no evil” with our data but nobody really knows. Cloud computing is another black hole.

Then our customers would program us with their products and services. They’d invite us to events and make us wear their corporate t-shirts to reinforce their message. It felt like Sunday church, except nobody believed their gospel.

Whenever a problem arose at work there was a team of lemmings to flood the room with excuses and Powerpoints full of poorly designed solutions. No one ever said to me “you must solve this problem or you’re fired.”


A normal job spreads problems across more than one person so you’re pretty safe. It’s how people can stay in comfortable madness their entire career.

In the side hustle world it’s different. I had to learn to think for myself. When I received poor programming from businesses, people and products I used, it cost me big time. I realized a lot of people do what’s in their best interests not mine. I had to learn to see through the bullsh*t and improve at evaluating people and opportunities. I made plenty of mistakes but I got better at it.

Tim Ferriss taught me to create a pros and cons lists for everything. I got multiple quotes for services. I asked hard questions to people who wanted to work with me. I stopped living in a house made of pillows where I couldn’t hurt myself. Instead, I got some bruises and fell down on my knees enough times to make them bleed uncontrollably.

Three separate website companies scammed me. Conversations I had in private got leaked online. Partnerships came and went. Content platforms went up and down with their strategies, and with it, my livelihood.

The path to a successful side hustle requires you to think for yourself and form your own opinions. Otherwise, if all you do is take second and third-hand information as gospel, you’ll fall flat on your face due to the hidden incentives being against you.

A life of no risk teaches you to be skeptical. You have to undo the programming.

A job doesn’t have a lot of risk. If the worst event happens then you can always get another one. There are record numbers of employers desperate to hire you. I’ve done plenty of online learning when it comes to side hustles.

Not one guru ever taught me how to take risks.

Our brain is programmed to avoid risks to stay safe. This explains why so many people are professional skeptics. They grow up in a work culture where risks are mostly prevented.

Then they get out into the side hustle world and have to sort through the bullsh*t. It’s not easy. So they quickly give up and let their skepticism take over. They blame fake gurus as the problem when it’s really their lack of courage to take a risk and see what happens.

Three websites I’ve tried to build in the last year have failed. It’s cost me a small fortune. And I’m fuc*ing smiling. Why?

The lessons I learned from how not to build a website have led me to a place where I now know exactly how to build a website like a pro. In fact, the lessons could turn into a separate business.

When I worked as a senior leader for a company that sold websites, I’d see people in the same situation lose their marbles. They’d call their mommy and get their lawyer to email us if the website didn’t make them money.

They failed to see that creating an online business with a website is their risk, not the website company’s. So they got conditioned to see every website company as a scammer, when the problem was their inability to take risk and have it go bad.

A side hustle equals risk. Take small risks and let them blow up so you can build your risk muscle. The more risk you get comfortable with, the bigger your side hustle empire can get.

What to do with the success

A friend of mine created a side hustle that became wildly successful. He got everything he wanted and more in a few months.

It all led to several years of dark depression.

The entire business got left on a laptop in a foreign country to rot away. I asked him what went wrong. “I don’t fear failure. I fear success.”

When your side hustle has some success it can all go to your head. You can think your god’s gift to humanity. The first sign is you oversell yourself with too many asks. The second sign is you give thank you speeches to random people on social media, like you’re accepting an Oscar. The third sign is you start counting numbers of followers. The fourth sign is you create some cheesefest personal brand that makes grandmothers around the world vomit. I could go on…

The first time I made $50,000 in a month I became a giant a**hole. I told one female manager at work “I could quit tomorrow you know, I don’t need this bullsh*t. My side hustle pays five times what this lame job does.”

Success gets to our heads. That’s why it pays to have people who can knock you back down to reality when your head gets too big. I intentionally have people do this for me via a verbal contract. They happily do it.

The last skill you need is to invest the profits. I see people doing well with their side hustle every day. Then they tell me they blew the money on some random purchase or let it sit in a no-life savings account been eaten up by 5%+ inflation.

Take a large amount of the profits and invest them in financial assets. These investments will help smooth out the ups and downs of the side hustle game.

A side hustle didn’t buy my time back. A side hustle that funnels money back into financial assets did. That skill is never spoken about by the gurus, so their followers end up stuck on the hamster wheel to nowhere. You can do better.

This article is for informational purposes only, it should not be considered financial, tax or legal advice. Consult a financial professional before making any major financial decisions.

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