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.
Because 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?
And does this look like a side hustler?
Note: I tend to shy away from taking pics, so these were the best I could come up with.
I’ve blurred out the faces of my Fam, since I’m fairly certain they wouldn’t want their pics plastered all over the internet.
And yes, my partner and step-sons are ALL over 6 feet. I was wearing heels in that picture, and could still barely reach 5 feet.
But anyway, when it comes to describing a side hustler — I’m clearly not an insta-influencer, or 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 rather read financial advise 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, I’m not giving financial advise, 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 definitely 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 that can be shared 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 out so loooong 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 the active imagination. A creative streak, if you will.
I mean, don’t most little kids have that? Whether it’s an imaginary friend …or super powers … or a pet dragon or unicorn?
For as far back as I can remember, I’ve always been on the hunt for treasure. Seeking out an adventure.
Looking for the pot of gold at the end of the rainbow.
Hunting for the clues on the treasure map, that 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, that would eventually lead me to some sort of shiny trinket or little gift. These were left by my mom, 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 catalogs and pamphlets, that my dad basically had to slam the front door in the face of a burial plot salesman.
Apparently I’d filled out a request card for some sort of freebie, in exchange for discussing the plans for my future remains.
I think I might’ve been 11 at the time.
But this guy was intent on speaking with me. Even after my dad explained how young I was, and that I clearly 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. 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
Through the years, I recall snippets of memories that have molded me into who I’ve become.
- My “cowgirl” phase — riding up and down the block on my little red bicycle. It 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 fee of candy 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. Handling 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 actually 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 …
- I also checked in with my partner on any side hustling he did as a child. His first side hustle was a paper route, which he delivered by foot. He started earning income delivering newspapers at the age of 10.
And who can forget your first side hustle as an adult? You’re at the point where you can’t really rely on your parents any longer, 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 college dorm rooms, at the college I actually attended. And let me just 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’d like 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 possibly 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? 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 a 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. Hustle how you want, when & where you want — it’s a free country, after all!
Take it from me, a middle-aged, average, every-day member of the community.
You don’t need special qualifications in order 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?
I’d love to hear your thoughts — Hit me up in the Comments!
Robin is a full-time business professional who has worked in the financial services industry for over 20 years. She is also a personal finance blogger who shares her first hand experience with the struggles of money and debt. On Mastering the Side Jam, she focuses on ways to maximize efficiencies to make & save money, pay off debt, and live your best life.
She has been been featured on The Money Mix, Rockstar Finance, The Financial Diet and Women’s Money Talk, and has been quoted in various online publications.