The Long Journey of a Side Hustler


Defying Stereotypes

Quick — when someone uses the term “side hustler”, what’s the first thing that comes to your mind?

  • A fast-talking charlatan, using sleight of hand to con you out of your life savings?
  • A 20-something jack-of-all-trades, picking up gigs to support video game downloads and extra beer money?
  • Or even an insta-famous social influencer promoting their must-see makeup hacks?

Well, I’ve got some interesting news for you.

The stereotypical side hustler has evolved over the years.

And here’s one you may have never thought would meet the criteria:

Middle-aged corporate professional with an aversion to social functions and an affinity for creative expression.

Does that sound like a side hustler?

I’m not an insta-influencer, online gamer, or slick dealer.

I’m just some lady from Anytown, USA, who’s trying to use her spare time to make some extra cash.

Am I a millionaire? Heck no.

I mean, if you’d instead read financial advice from an expert who has made tons of money with various investment accounts — I might be able to point you in that direction.

But I’m not an expert, and I’m not giving financial advice, and I don’t have any magic tricks up my sleeve to make you (or me) a millionaire.

Why Should You Listen To Anything I Have To Say?

They say with age comes wisdom.

Isn’t that a contrite little saying? I mean, I guess it might be true in some instances. But not in all cases.

Because in my adult life, I’ve messed up plenty.

So I’d rather say with age comes experience. And with experience, there is learning. And with learning, there is eventual wisdom to share with others.

I certainly cannot tell you the right thing to do for your particular situation. All I can do is share what I’ve learned, with the hope you might pull some value out of my stories.

And these are stories that started so long ago.

Wanna know how this side hustler got started? Well, we need to go back to the beginning.


Dream a Little Dream

When I was a little girl, I had quite an active imagination. A creative streak, if you will.

I mean, don’t most little kids have that? Whether it’s an imaginary friend or superpowers or a pet dragon or unicorn?

For as far back as I can remember, I’ve always been on the hunt for treasure. I was seeking out an adventure, looking for the pot of gold at the end of the rainbow.

Hunting for the clues on the treasure map will lead to where ‘X’ marks the spot.

I remember playing in the sandbox in my backyard, sifting through its contents, mining for gold — or actually, “fool’s gold“.

Or following clues around the house would eventually lead me to some shiny trinket or a little gift. My mom left these, and I remember seeing the playful twinkle in her eyes when I’d come running up, exclaiming, “Look at what I just found!!”

Oh, and dear Lord, the freebies — I went after everything! It didn’t matter if I needed it or even truly wanted it. If it was free, I was grabbing a fistful.

Not So Dearly Departed

There’s even an old story of me being so fond of sending away for free catalogues and pamphlets that my dad had to slam the front door in the face of a burial plot salesman.

I’d filled out a request card for some sort of freebie in exchange for discussing the plans for my future remains.

I might’ve been 11 at the time.

But this guy intended to speak with me even after my dad explained how young I was and that I wasn’t looking to buy a burial plot.

Finally, he decided enough was enough and just slammed the door in his face. (That part still makes me giggle).

Okay, so I’ll admit hunting for treasure and scavenging for free stuff doesn’t exactly equate to side hustling.

But I think it shows a propensity for discovery. It was finding value and advantage in something that might be put to good use.

When’s the last time you went searching for treasure?

Next Phase: Side Hustler in Training

I recall snippets of memories that have molded me into who I’ve become through the years.

  • My “cowgirl” phase — riding up and down the block on my little red bicycle that had training wheels on it still. But to me, it wasn’t a bike. It was my trusty horse, Licorice. And I charged the local kids a candy fee for rides on my “horse”.
  • Receiving a metal detector for Christmas, then bringing it with me all over town, to the park, to the beach, to see what I could find and possibly resell.
  • Various garage sales — always looking for a bargain or a sweet deal. Even holding our own garage sale in our driveway, writing prices on little white stickers to be placed on each item. Negotiating deals on lightly used pocketbooks or a NIB Crock-Pot. I handled all of the sales and calculations with my older sister while our mom kept a close eye on us from inside the house.
  • And there were multiple talent shows we put on with our cousins. Did we charge a fee for those performances? Probably not. I’m pretty sure we just worked for tips. Some of these may even exist on video somewhere.


Adulting 101

And who can forget your first side hustle as an adult? You’re at the point where you can’t rely on your parents anymore but aren’t quite earning a full-time income.

Maybe you’re working part-time through college. But it’s a change in landscape, where reality sinks in. You are now an adult who has to pay for things. How do you adapt? Here are some side hustles I remember doing through those years —

  • Filling out and mailing in paper surveys (pre-Internet!)
  • A summer job cleaning dorm rooms at the college I attended, and let me tell you about the treasures we’d find. A bunch of privileged rich kids (which I was not), and they’d leave everything behind. From clothing to CD collections to actual TV sets. But that’s a story for another day.
  • And then there was the time I signed up for a paid drug trial to have my wisdom teeth removed. All I can say is thank God I wasn’t given the placebo.

Are side hustlers born or made? Is it nature or nurture — or a product of our circumstances and surroundings?

I want to think my natural curiosity and creativity as a child paved the way for my future side hustling tendencies. But maybe I was also affected by the frequent need to make ends meet. The necessity of stretching a paycheck as far as it could go and then finding one or two band-aids to keep it all together until the next payday.

Had I been better at managing my finances as a young adult, would I be the side hustler I am today? Unfortunately, the world may never know.

So What Does a Side Hustler Look Like?

Side hustlers come in all shapes, sizes, orientations, and ages. It’s not a one-size-fits-all type of deal. So if you’ve got the hustle in you — no matter the motivation or reason — by all means, embrace it.

You don’t need to fit a certain mold, or meet particular criteria for acceptance into the Side Hustling club.

No one is going to look you up and down and revoke your “Side Hustler” card for not hustling hard enough. So hustle how you want, when & where you want — it’s a free country, after all!

Take it from me, a middle-aged, average, everyday community member.

You don’t need special qualifications to be a side hustler. But having the hustle in you sure makes life interesting!

Do you have the hustle in you? When’s the last time you went looking for buried treasure? 

What are some fun or creative ways you’ve tried to make some extra cash?

How has your childhood or upbringing affected your relationship with money or side hustles today?