It was supposed to be “Career Day.” I thought—okay, let’s do something fun, like a handyman or a farmer.
But then I blinked, and he walked out of his room like this.
Beanie pulled low, plaid shirt tucked into jeans, and that marker beard…
I asked what he was supposed to be, and without breaking character, he held up that cardboard sign like it was a résumé.
“Will work for candy.”
He said it with the dead-serious tone of someone who’s seen things.
I tried to laugh, but he just stared at me like he was the parent and I owed him Skittles for rent.
It took me a second to process. My eight-year-old son, Miles, was standing in front of me dressed like a tiny street hustler, asking for candy as payment. The guy who barely knew how to tie his shoes last year was now some sort of street-smart, hardened character, with a cardboard sign for emphasis. I could feel a laugh creeping up my throat, but it caught in my chest, as if his seriousness was contagious.
“Miles, sweetie,” I said, trying to sound calm, “what are you wearing?”
He straightened his tiny frame, pulling his beanie down even further over his forehead, before nodding. “A hustler, mom. A street hustler. You know, like the ones who stand at the corner and sell stuff or ask for change. You said to be creative.”
Creative. Sure, that sounded like something I would have said. But this? This was a whole new level of creativity. And I hadn’t even realized that he was picking up on things like this from the world around him.
“Why a hustler, Miles?” I asked, already feeling guilty that I wasn’t sure what part of our daily lives he had observed that led him to this moment.
He looked at me like I’d just asked him why the sky was blue. “I don’t know, Mom. It just seemed cool.”
I was still in shock. My son had never shown any interest in street culture or any sort of tough exterior. He was a sweet, funny, and sensitive boy who liked drawing comics and playing with his toy trains. Where had he gotten this idea?
“Can you please just take that marker beard off?” I asked.
“No,” he replied, eyes narrowing. “It’s my brand.”
Brand? He’s eight.
But the little hustler wasn’t done with me yet. He walked past me, grabbed his backpack, and gave me a sharp, adult-like nod, as if to say, “You’re in my world now, lady.”
I blinked. What was I supposed to do? I stood there for a few seconds, trying to fight the urge to burst out laughing or yell at him. Was I doing the right thing by letting him dress up like this? And what was this sudden desire for him to act like he had seen it all?
I looked over at the clock. We were running late. It was career day at his school, and I didn’t want him to miss it. I quickly decided that maybe I could just roll with it. I grabbed my keys, made sure to pat my hair into some semblance of order, and we were out the door.
The drive to school was strange. I kept glancing over at him, trying to gauge if this was just a phase or if I was witnessing something deeper. Was he trying to get attention? Was this his idea of standing out? Or had he picked up on something—some kind of raw, urban energy—that made him think this was how he was supposed to act?
“Do you want me to walk you to class?” I asked, trying to regain some sense of normalcy.
“No thanks,” he replied, not looking at me. “I got it.” His voice was calm, but his little hands gripped the cardboard sign so tightly I could see his knuckles turning white.
I wanted to ask him what he was thinking, what had gone through his mind to put this whole thing together, but part of me was afraid to ask. Maybe I didn’t want to know how much of the world he was already seeing that I hadn’t fully prepared him for.
He got out of the car and looked at me with a raised eyebrow before heading into the school.
“Good luck, hustler,” I called after him. He didn’t turn around.
As I drove away, I felt a strange knot forming in my stomach. Something about the whole situation felt wrong. Not because of the outfit or the playful tone of his act, but because I wasn’t sure where it had come from.
The day went on, and I couldn’t shake the thought of him standing there in his little street hustler costume. What had gotten into him? I tried to focus on work, but my mind kept drifting back to him, wondering if this was some kind of cry for help or if it was just a phase.
After school, I picked him up, and the first thing I noticed was the grin on his face. He was practically glowing.
“So, how did it go?” I asked, unable to stop myself from smiling at his obvious excitement.
“Best day ever!” he declared. “Everyone loved my look, Mom. I made like five people laugh, and Mr. Willams—my teacher—said I was creative.” He paused. “Oh, and I traded my candy for two packs of gum and a pen!”
I couldn’t help but laugh. “You traded candy for gum?”
“Yep,” he said proudly. “I was hustling!”
A wave of relief washed over me. It wasn’t as bad as I thought. He wasn’t out there robbing anyone or making bad decisions—he was just playing a part, exploring some creative idea. But still, the whole thing had been odd.
“Did you learn anything?” I asked, genuinely curious now.
“Mmm… yeah,” he said, thinking for a second. “If you want something, you’ve gotta know what you have to give. You know?”
I blinked. My eight-year-old had just given me a miniature life lesson.
It took me a moment to process that. Hustling. It wasn’t about the negative connotation I had attached to the idea. It wasn’t about manipulation or anything shady—it was about understanding that life often asks you to trade something you have for something you want, and knowing how to make those exchanges in a fair and creative way.
I smiled at him, feeling a little more at ease. “I think I understand. Maybe you’ll be a businessman one day.”
“Yeah!” he said, excited. “I’ll sell candy and gum. I’ll be the best!”
We spent the rest of the evening laughing, him bouncing ideas off of me, and me feeling grateful that he had such a sharp mind.
That night, as I was tucking him into bed, he looked at me with wide eyes and said, “Mom, do you think I could really be a businessman?”
I kissed his forehead. “I don’t know. But I do know this: whatever you choose to do, always be true to yourself and don’t forget to keep laughing. People will appreciate you for who you really are.”
As I walked out of his room, I couldn’t help but think about how much of life we had to learn as we went. We had to make trades, take chances, and most importantly, keep moving forward—even when things got tough.
Life was all about hustle—real or imaginary. And sometimes, you didn’t even need to know where you were headed, as long as you kept your spirit up and your heart open.
The next morning, Miles got up early, ready to face whatever new adventure came his way. He still wore that smile of a kid who had learned something big, even if it was just one small lesson in the hustle.
And as for me? I was learning, too.
Life had a funny way of teaching us things when we least expected it. And sometimes, it came from the most unexpected teachers—like an eight-year-old boy dressed as a tiny street hustler.
Share this if you’ve learned something from the unexpected moments in your own life, and like it if you’ve ever had a kid teach you a lesson you didn’t see coming.
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