The $16 Transaction That Paid Me Back in Joy

The day had just begun here in Chicago when the storm rolled in. The air was cold, the streets were quiet, and I was mentally preparing for a long, slow day indoors.

Then, the doorbell rang.

I opened the door to find a young boy, bundled up in winter layers. 

He looked like a middle-schooler, and he had a well-worn snow shovel in his hand.

He offered a simple transaction: "$16 to clear your driveway."

It had barely snowed, and I knew the biggest part of the storm was yet to come. 

I initially told him to come back later. But the earnest expression on his face—the look of a person hunting for their very first customer—made me pause.

"Okay," I said. "Let's do it."

The Hustle and the Single Shovel

As the work began, I realized it was two kids. And as the snow lightly fell, I watched them work from my window camera.

This is what truly surprised me: They only had one shovel between them.

They took turns. While one was pushing snow, the other, when his partner was tired, would use his feet to move the snow, simply refusing to stand still. This was pure, unplanned hustle.

I couldn’t settle down while they were outside. 

Even my wife asked if we should offer them hot chocolate or something warm. 

We were instinctively worried, viewing the task through the lens of adult comfort.

Soon, they were done.

What the $40 Really Bought

When they came back to the door, we asked their names: Adele and Syeed, both students at Scullen Middle School, living nearby.

We handed them two chocolates and $20 each. Their reaction was instant and powerful: a surprised jump, huge smiles, and a genuine shout of, "You are the best!"

They walked away happy, their winter boots crunching in the fresh snow.

Their sheer joy over the small reward really made me think.

These kids didn't need to be out there. 

They could have been warm at home. 

But they chose discomfort. 

Someone must have inspired them, or supported them in making this choice.

What I realized was this: That willingness to simply show up and embrace the difficulty—the desire to earn the first dollar, regardless of the single tool or the cold—is a spirit we can’t teach in a textbook.

We, as adults, often try to make everything comfortable for ourselves and for our kids. 

We shield them. 

But watching Adele and Syeed reminded me that the truest joy and the most valuable lessons come from that simple, willing act of showing up for the hard work.

Sometimes, the best return on investment isn't the clear driveway, but the brief, surprising encounter that reminds you of the essential things in life.