Here’s how you should think about it.
Mark Manson had perhaps the weirdest side hustle ever.
Early in his career he got a job in finance. He also liked to write on his blog after work. Before he pivoted to writing for a mass audience about the darker side of self-improvement, he wrote about how to pick up chicks.
He got inspired by Neil Strauss’ famous book “The Game: Penetrating the Secret Society of Pickup Artists.”
Pretty soon enough people looked up to Mark that he could make a living from giving dating advice online.
Six weeks into his finance career he oddly went up to his boss and told him he was quitting to sell dating advice online full-time. He says that’s about as high as it gets in his “didn’t give a f*ck” hall of fame.
Bloody legend.
That bold move helped Mark survive the aftermath of the deadly 2008 financial crisis. In a way, it was a blessing not to be in working in finance after what went down.
With the odds of a global recession this year increasing, it’s a good time to think about getting a side hustle, or doubling down on your current one.
Kapil Gupta wrote in 2019 about how we tell ourselves we love our jobs.
He encourages us to “investigate further.” Often we say this because we’re too afraid to face the truth or we’ve never given ourselves the chance to try other forms of work.
It’s far too easy to settle for second-best than make a change. Kapil thinks even business owners need to rethink the way they imagine their work.
If you own a company, I can virtually guarantee that it has made a “worker” out of you.
Customers can enslave us. We become addicted to their money. And when we do, the thought of a side hustle gets buried. Now you know why the idea of side hustles brings to the surface a lot of pain for people.
(Follow these steps in no particular order.)
Understand why bedroom startups destroyed garage startups
Aaron Dinin wrote a story recently about why Steve Jobs-style startups and side hustles don’t get built in garages anymore.
In the old days you made a product with your side hustle and marketed it. In the new days of bedroom side hustles, you build an audience first and then figure out how to monetize it later.
You don’t even need to build a product. You can affiliate anything once you have an online audience.
Action step: build an audience online.
“Behind the most sexy outcomes, there’s always a very boring system”
Daniel Bustamante is a Zapier consultant and said this.
Side hustles that succeed have systems. I recently took what was my online academy side hustle and wrote an entire playbook. This playbook serves as a system that can be replicated without me.
Systematized side hustles grow faster because you can hire freelancers to help scale time-intensive tasks. No one can help if they don’t have a system to follow. And teaching freelancers 1–1 is too time-intensive.
Action step: document your side hustle in Notion or Roam.
Underrated side hustle trait: “Thick skin”
Recessions kick you in the genitalia by design.
They’re a wake-up call, a cold shower at 4 am. The big egos become small. The greedy become humbled. It takes thick skin to give your side hustle all you’ve got and ignore the critics.
The key isn’t to beat a recession. It’s to survive it.
Action step: practice non-reactivity. Turn down the ‘recession media.’
Close open doors
Entrepreneur Tom Bilyeu says side hustlers need to pretend they’re standing in a room with 1000 doors. The goal is to close 999 doors.
In other words, say no a lot more times to increase your focus. Too many open opportunities become a distraction, not an advantage.
Action step: ask yourself, “What’s one yes I could give that would make all the other noes worth it?”
Don’t do it alone. Too bloody hard, mate.
Most people I encounter give up their side hustle within 90 days if they don’t see results. Not because they’re dumb, but because the only voice in their head is their own.
You can’t go far with a side hustle on your own. A community helps you go further. You grow together.
Action step: join a Slack/Discord of like-minded side hustlers.
Lean into the fear
Side hustles can lead to a greater sense of freedom.
The problem, according to Roberto Carlos, is freedom is scary because it implies more responsibility and self-direction.
No angels come and hold your hand in the world of side hustles. This leads even the tough Rocky Balboas to have extreme fear.
Here are the two choices you have…
Action step: feel the fear and take action anyway.
Stay away from the $1M distractions
Entrepreneur Justin Welsh taught me to focus on how to make $1 online, not $1M.
Big side hustle goals are too big to achieve, especially when you’ve still got a job. What you want is to unlock your side hustle psychology. That shift happens when your side hustle makes a few dollars.
Suddenly your brain says “this is possible.”
Action step: sell one $20 eBook on Gumroad.
“I’ll do it someday” versus “today is the day”
Daily action is what progresses a side hustle. The phrase “I’ll do it tomorrow” has killed many side hustles.
Action step: focus on what tiny actions you can take today.
Have no clue what you’re doing
The reason side hustles aren’t called businesses and the people who do them aren’t entrepreneurs is because both those descriptions suggest you need to know what you’re doing.
The word side hustle is code for experiment.
Experiments often don’t work out. They fail, even. They’re not-so-serious. If you can do a side hustle for a year and have no clue what you’re doing, it’ll probably become successful. That’s the subtle barrier to entry.
Action step: commit to one side hustle for the next year. No switching.
Full-time work isn’t an excuse
Justin Welsh also reminded me that working a job is a common excuse for not having a side hustle. He says even with a full-time job you can still:
– Consult
– Freelance
– Write eBooks
– Create video courses
– Write a paid newsletter
– Do cohort-based coaching
Why? Because the barrier to entry is low.
Surviving a recession means having a little extra money to wear as armor against any nasty consequences.
It may surprise you … but a side hustle that can make $274 a day can create a $100K income. Aim for small numbers like this and let your effort compound into online leverage that’ll look spectacular once the recession is done.
