The History Of The Side Hustle
How we got here and where we’re headed.
When I was 12 years old I took up landscaping in the summertime.
Mowing lawns, trimming hedges, raking leaves,
Whatever I could do to make $10.
After college, I started a men’s clothing company, called Leather & Cotton, which I ran as a side hustle for 3 years before it began making hundreds of thousands of dollars and then millions; turning into my full-time job.
That “side hustle” changed the trajectory of my entire life.
In the early 1930s, during the Great Depression, people trying to make ends meet did things like:
- Selling homemade fudge
- Selling newspapers
- Shoveling snow
- Making handwoven baskets
- Making and selling quilts
The list goes on.
This wasn’t the beginning of the “side hustle”, of course.
Doing random things for money goes back as long as money has been around.
And before money people bartered for things; the beginning of work trade.
The phrase “side hustle” was first used back in 1950 when traditional jobs dried up and people needed to put food on the table.
Since then, we’ve seen it go through many stages.
From Brian Winch picking up trash as a side hustle in the early ’80s,
To Sophia Amoruso starting Nasty Gal on eBay in 2006,
And now millions of people making money through e-commerce, social channels, blogging, and freelancing outside of their normal jobs.
If there’s one thing we know about the human race thus far:
We are extremely industrious.
When good enough isn’t good enough, we go out and find more.
If an employer isn’t doing a good job at keeping our attention,
We will find a way out.
We will work our side hustle until it’s our main gig.
There’s no such thing as “golden handcuffs” anymore.
Keep your money, we will find another way to live and work for ourselves.
The idea of the side hustle, in cultures all over the world, has single-handedly shifted the paradigm of how we view work-for-money transactions.
We always have other ways to make money.
Now more than ever, we can choose our work and the format in which we do it.
You probably noticed in the list above, from the Great Depression era, that the things people did back then for extra money, are’t terribly different from what people do now.
We just have online marketplaces for those services now.
We sell homemade fudge and other goods through Shopify sites.
We sell handmade baskets and quilts through Etsy.
We sell services like snow shoveling or building Ikea furniture through Facebook Marketplace and Task Rabbit.
We sell writing and newsletters through Medium and SubStack.
We rent out our cars on Turo and our homes on AirBnb.
We even sell SkillShare courses for how to make money on these platforms.
So where do we go from here?
What is the future of the side hustle?
Well, the same as it always has been… us.
You and me.
It’s “What value can I provide?” and “Who will buy it?”.
The levers we pull will change over time.
Street corners, newspapers, brick and mortar, websites, social media, eBay, Etsy, Medium, SubStack, SkillShare, the Metaverse, and beyond.
But it will always, always come back to:
What value can I provide? (Who am I?)
And who is going to buy it? (Relationship building)
Over half the workforce is now freelance or works for themselves in some way.
It seems clear that this trend will continue throughout the century until nearly everyone works for themselves in some capacity.
Because we want so badly to delete the 9-to-5 lifestyle from existence.
Imagine Fortune 500 companies run entirely by freelancers from all over the world.
No office, no home-base, just people waking up, doing their thing on their own schedule, and then carrying on with the rest of their lives.
The side hustle movement has us barreling towards a future where people are paid for their work and the value it provides, not the hours they spent on it.
It can be difficult to keep up with all of the technology that helps us get there,
But we don’t have to worry about that so much if we can just keep in mind this simple truth:
“You have skills and knowledge that people will pay for,
just find a way to put it in front of them.”
The future is bright, my friends, walk forward with confidence.
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