The Side Hustle Juggle: How A Fair Game Taught Me The Secret To A Happy Life (Part I)

“Guess your weight! Guess your age!” the carny’s side hustle pitch barked with enthusiasm. The hint of a playful southern drawl made it all the more alluring.

To this day, I love watching people play the “Guess Your Weight” game. There are several variations on this theme. The barker can guess your weight, or your age, or your birth month. With all those combinations, it’s got to be a surefire winner, right? And just look at those huge rewards surrounding the little booth with its carnival-like scale. Those gigantic furry bright multi-colored animals dangling from strings above the barker’s head just beg you to play the game.

There’s only one catch—you can’t win the big prize without first collecting a stack of smaller ones. The small prizes don’t look bad by themselves; they just look bad compared to the gigantic goodies orbiting the stand.

The bright lights entranced me. The dazzling neon prizes swayed like promises I couldn’t resist. But my grandfather’s stern warning kept me grounded. There I stood, a naïve teenager stuck like a middleman between the carny’s grin and my grandfather’s scowl. It was like the interplay between the sugary air fed by the aroma of cotton candy and the acrid midway dust kicked by the feet of thousands of fairgoers. In a strange way, both had me hooked.

Discipline won the battle that day. I walked away. But imagination would rule in the end. By nightfall, destiny beckoned. I knew I’d be back.

I didn’t know it then, but that summer, the game within that game would teach me how to juggle my dreams into a happy life.

Fair Games, Lifelong Lessons

To my young mind, the Guess Your Weight game was an impossible-to-lose proposition. I could count three confident reasons to prove this. First, it’s tough to guess your weight within the range. Second, some people don’t look their age, so they are surefire winners. And third, your birth month is purely random.

“Scales lie. Smiles cheat. And even if he loses, he wins,” Grandpa snapped. He made no pretense about his academic prowess. He just knew what was right and what was wrong. And he believed carnival games were wrong. He finished his lesson with, “It’s all rigged, Chris. Ask the carny how much the prizes cost. Then do the math.”

His curt comeback didn’t faze me. He seemed to focus only on the monetary portion of the equation. He never quite appreciated the romantic value of the game. Grandpa missed the romance—the proud boyfriend, one arm carrying the larger-than-life, cute, furry animal while his adoring girlfriend snuggles ever closer to him, wrapped around his other arm. Priceless. Who wouldn’t pay for that?

Still, he was my grandfather. I respected him and his deep experience. So, one day, I furtively spied on a particular “Guess Your Weight…” booth. Grandpa was right. The fellow engaged in casual banter with the customer and then, more often than not, correctly guessed that person’s age within the seemingly narrow spread.

The people left, having spent their money. The game guy sat in his chair for a much-deserved break. I approached the carny in full pizza stand gear, so he knew I was one of them. I asked him how he could be so good at guessing. He shocked me by confirming what my grandfather said in an instructive, matter-of-fact manner. It was as if he felt he had to mentor me. I left confused, but even more captivated.

That evening, as the Fair’s lights dimmed and the last of the crowd shuffled home, I went to the same carny who spilled the beans earlier. By now, he recognized me. We exchanged pleasantries—casual talk, if you will. Like a sly kid detective, I used the same hustle he had revealed to me earlier. I was wondering if he was just as unsuspecting a mark as his customers.

Finally, I asked him, almost as an aside, “So, how much do these things cost you anyway?” I pointed to the small prizes one must collect by the armload in order to obtain a single big prize.

In the dark of that night, the carny’s eyes quickly scanned the immediate vicinity. No one was within listening distance. Under his breath, but into the microphone, he whispered, “About a penny.” And then he quickly changed the subject.

There’s a 1 in 12 chance the carny would correctly guess the birth month. Statistically, for every 12 customers, the carny would correctly guess one and miss the other eleven. Each customer paid the carny $1 to play. The carny, therefore, took in a total of $12 for 12 customers. The cost of one prize is, let’s be charitable and say it’s 5 cents. The carny awarded eleven prizes at a cost of 5 cents. Therefore, for every 12 customers, the carny had net a marginal profit of $11.45 or an incredible 1,908% return. My grandfather was on to something. But so was the carny.

Grandpa’s truth was the strategy; the carny’s hustle was the move. Together, they represented an intricate dance. A subtle game of Yin and Yang, cat and mouse, a playbook of structured strategy and bold hustle.

Juggling More Than One Side Hustle with a System

A decade at the Erie County Fair working in my grandparents’ pizza stand exposed me to the world of the carny, that Cauldron of Commerce, Crucible of Capitalism, Wild West of Winning Wealth. That’s what lit the fuse, what sparked my intrigue in making money on my own. It was the challenge. It was the game. I wanted in. I just had to figure out a way to do it. I had to come up with a system that worked.

The window of opportunity, though, doesn’t wait. When it opens, you either jump through it or you spend your days wondering, “What if…” I’m not the kind of person who likes to ponder, so I jumped, guessing I’d figure things out on the fly.

In that vein, I didn’t seek out to become a baseball card dealer. The opportunity organically fell into my lap. At an age when most of my friends were moving out of collecting cards, I was moving in. Without the burden of childhood biases, I immediately treated it like a business. And then it became one.

All those tricks and rules I learned working at the Fair, I put to good use. My first big card deal—a Pete Rose (ironically nicknamed “Charlie Hustle”!) rookie card trade—netted a tidy profit, proving the carny’s hustle worked.

Then college came, and my days of dealing cards shuffled to a backseat priority. I didn’t stop doing it, but it was small potatoes once my next side hustle took root—a pivot to political polling for multiple presidential campaigns. Polling proved a lucrative gig that taught me precision, like Grandpa’s strategy, balancing both hustles with my studies.

How does a college sophomore majoring in physics and astronomy (with an equally rigorous dose of math) find himself polling for presidential primary campaigns? Naturally, when the opportunity presents itself. While the full story is best left for another time, the concept of “time” is the more important question here. How did I find the time to juggle all these activities?

That’s where the magic happened. Fate sent me an obscure book called Targets: How to Set Goals For Yourself and Reach Them! It pretty much accidentally appeared in my mailbox.

Rather than return it, I read it. Good thing, too. That book inspired the very system I had been searching for all along. It allowed me to juggle numerous activities, experiencing them to the max, without getting burned out. I set weekly goals for polling calls, prioritizing like Grandpa, and hustling for card deals, like the carny. Suddenly, the smorgasbord of opportunities before me was not so overwhelming. And what a sumptuous feast it was.

More importantly, I didn’t fall for the usual “moving on” attitude so many fall victim to. I didn’t forget my past for the sake of my present. I brought it along for the ride. Want an example of this? One of those political campaigns ran out of money and couldn’t pay me. I jokingly said, “You can pay me in baseball cards.” The campaign manager—older than me—said, “I’ve got some old baseball cards I don’t want anymore.”

And that’s how I obtained rookie cards of Hank Aaron, Roberto Clemente, and several other 1950s Hall of Famers. Based on today’s prices of those cards, that transaction turned out to be one of my most lucrative side gigs ever. But it wouldn’t be my last side hustle.

My system worked like a charm. Technology would later make it unstoppable. I didn’t know then how tools beyond my typewriter would juggle my side hustle dreams.

Next: The Side Hustle Juggle: How A Fair Game Taught Me The Secret To A Happy Life (Part II)

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