
WHEN THE SMART IS BEING OUTSMARTED ON THE STREET GAME.
"You may not know how it feels… until it happens to you."
I used to hear that statement, but now I understand it. If it has never happened to you, you won’t fully get it. But if you’ve ever experienced something like this on the street, I’m sure you’ll understand even before I finish this story.
This is a long read, so please stay with me as I recount this heartbreaking experience.
It was a Monday morning. I wasn’t feeling too well, but I couldn’t place what exactly was wrong. I just felt off. Still, I told myself, “It’s too early for this. Let’s get to work.”
When I got to work, I felt reluctant to do anything. But again, I pushed myself, it was a new week, and I had to do better.
I arranged my space and displayed the goods for sale. By 8:30 a.m., I was ready for the day’s business.

I noticed a shoe cobbler nearby and called him to fix my shoe. I was standing by the door when a bike passed by with a passenger. The passenger looked at my store and asked the rider to turn back.
He walked in confidently, like he owned the place. I didn’t think much of it at that time, I’ve seen customers act like that before, even claiming they own the store with my boss.
He asked for the price of the Jalabia on the mannequin. I told him, and he tried negotiating. He said he didn’t like the grey color, so I brought out other options and recommended a navy blue one.
Then he asked for shoes. I said I would confirm the price, but he told me not to bother, that he wouldn’t be picking them.
(If you’ve had a similar experience, you probably already understand where this is going… but let’s continue.)

Reluctantly, I went along. He walked too close behind me, which made me uncomfortable, so I tried to create space.
He picked a sweat sweater, requested two perfumes, and a polo. Altogether, everything was almost ₦200,000.
During this process, I was also charging his button phone because he said his battery was low.
When it was time to pay, I asked, “Cash or transfer?” He said transfer. I gave him the company’s account details and asked for a receipt since I don’t receive alerts directly.
My boss had previously instructed me to always call and confirm payments… but at that moment, my mind was blank—clouded. As he was about to leave, I asked for his name, phone number, and proof of payment.
Everything he gave me… was fake.
At that moment, it hit me. I felt dumb. I felt stupid. I was angry at myself for not noticing any signs, and for being outsmarted.
What hurts the most? I was genuinely happy about the sale. The business needed it. I even posted excitedly on the company’s WhatsApp that we had a great walk-in customer… not knowing I would cry later.
In the afternoon, my boss messaged me. I told her everything with excitement only for it to turn into heartbreak.
I tried tracing the number, and it led nowhere. I checked the bank details, it was a different identity. Social media, nothing. Even CCTV didn’t help. This man came prepared.
I was consoled. I was corrected. I prayed a deep C.A.C. prayer. I tried to process everything. I slept over it. And now… I can finally write about it.
My friends were shocked.
“Are you sure it’s you, Ife?”
“You always detect things like this!”
“How did this happen?”
And honestly… I kept asking myself the same questions.
My boss’s husband tried to lighten my mood. My boss stayed strong, even in the chaos. But I still felt the weight of guilt.
Now I understand something deeply,
If it hasn’t happened to you, you won’t truly know how it feels.
Because right now, I understand the pain of the people I used to console.

Being outsmarted on the street hurts.
Let’s update our street OT. Whether you think you’re street-smart or not, you need to stay alert, because the street can happen to anyone.
You thought this was one of Tomi’s fictional stories?
I wish it was.
Have you ever experienced something like this? Tell me in the comment section.
All images are mine.