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The Biggest Problem with Side Hustles That No One Talks About (And Can Keep Your Income Low)

by | Sep 18, 2023 | Making Money Online, Money

The idea of side hustles has become wildly popular.

Peak popularity hit in 2020 when some accused former President Donald Duck of treating the presidency as a side hustle to his other main hustles. I don’t do politics so I’ll let you decide.

The point is, are side hustles really the answer to more money & freedom?


The biggest problem with side hustles is they can make you think small.

Instead of going all-in on an idea a side hustle can force you to only do it part-time. You can accidentally put in minimum effort because it’s not the main gig. A side hustle lets a lot of people off the hook.

A side hustle can even be procrastination in disguise.

Let’s say you decide to write as a side hustle. You can easily start to consume a million courses and watch endless Youtube videos (designed as subliminal ads) to learn more.

This learning makes you feel like you’re making progress. In reality, you’re not. You’re just failing to start.

The side hustle is a distraction more than the daily motivation you get from taking action and seeing results from your experiments.

And your side hustle can easily become 10x smaller than your original vision. In the example of writing, instead of publishing big essays and meaty newsletter editions, you can find yourself publishing one-sentence tweets and thinking you’re a god.

Jumping off a cliff into the unknown isn’t the answer either

The other side of the debate says “Quit your job you pu$$y and make the jump, then see what happens.”

They say “This is your life’s work we’re talking about, pal.”

While I get what they’re trying to say, they’re just plain wrong. Before you decide something is your life’s work, shouldn’t you collect some data, run some experiments, and make sure?

Seems dumb to just hope and pray.

And if you quit your job and cut off your income, and your 10 minutes of side hustle experience don’t work, then isn’t that a bad idea?

Without an income you become desperate. You do things that could blow up or ruin your reputation because you need money. The answer as always lies somewhere in the middle of these two extremes.


The formula for a side hustle that (actually) works

All of this side hustle pain can be avoided.

1. Do 20 hours a week of work

Dedicated side hustlers spend a meaningful number of hours a week on their project. Aim for 20 hours or more to prove to yourself you’re serious. This will happen before and after work and on weekends.

2. Think big and stay big

Avoid thinking small at all costs.

All of you reading this are smart enough to know if your side hustle idea is too small and you’re playing it too safe.

My approach is to think big and the worst that can happen is you slightly miss the mark, which you never would have come near in the first place if you didn’t think big.

The big dreamers always become the high achievers.

3. Have a plan to go from side hustle to main hustle

I like side hustles because they de-risk your life.

It’s smart to take risks but it’s dumb to hope and pray. A good side hustle has a balance. You take risks after hours and if they don’t pay off, your income is protected.

If they do pay off then you have an additional income stream.

When I had a 9–5 banking job, I worked on my writing side hustle after hours. I had a plan in place to migrate. I said to myself, “Once I make $100K a year from writing I will go full-time.”

As reality would have it, I hit the number and waited a bit longer. But I did make the jump when it finally made sense. My plan included going from five days of 9–5 work down to four and later three.

When I got down to 4 days, I had enough evidence my side hustle was going to work that I quit instead of drop to three days.

Plans don’t always work out how they’re supposed to, but they get you further than having no plan at all.

4. Get accountability

Side hustles can get lonely.

And no one talks about this. I was part of several groups full of other side hustlers that had similar goals. I got to witness how many different types of people migrated from 9–5 work over to their side hustle that became their main hustle.

I borrowed ideas from each person to form my strategy.

When I finally made the jump, I had people to talk to and calm me down on the hard days. These same people kept me accountable, too. They made sure my writing didn’t stay a side hustle forever. They challenged me to experiment and take more risks.

Find a community of people with side hustle goals, then join.

Final Thought

You can make more money from a side hustle than your job if you have the right strategy and stick at it.

Don’t let a side hustle make you think small or cap how much money you think you can make. At the same time, don’t go all-in on some half-backed idea and think you’re going to be a millionaire in 30 days.

Act smart. Use the middle ground. Start a side hustle and slowly migrate it to become your main hustle when the data and income says to.

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