I Felt Stupid Asking for This… Until It Worked
How one uncomfortable question helped me stop settling and start asking for more
I was sitting in a café, writing a short story, when the server brought my coffee.
“Sir, are you a writer?” he asked. “I see you writing here often.”
“Yes,” I smiled, trying to get back to my story.
“Sir,” he continued, “I bought a book on entrepreneurship yesterday. It has mixed reviews. Do you think it’s worth reading?”
Before I could answer, he rushed away and came back with the book.
I took it, slightly annoyed, but his curiosity felt genuine.
It was about starting a business in a month.
I skimmed through it. Most of it was basic.
Then one line caught my attention.
Practice the art of asking.
The author said most people don’t lose opportunities because they lack ability. They lose them because they don’t ask.
It wasn’t new advice. But it felt uncomfortably relevant.
There was a deal I was working on. I knew I deserved a better offer.
But I hadn’t asked.
I didn’t want to risk losing it.
I handed the book back.
“It’s good,” I said. “You should read it.”
He smiled. “Thank you, sir. Let me know if I can help you with anything.”
I paused.
Then I said, “Well… I come here daily. Can I get a discount on my coffee?”
He looked at me. Then at the cup. Then back at me.
It was a 200-rupee coffee. Roughly two dollars.
His expression said everything.
This man is asking for a discount… on this?
He shifted uncomfortably.
“Sir… I can’t,” he said. “You’ll have to ask the owner.”
He pointed towards the counter.
For a moment, I felt stupid.
Asking for a discount on a two-dollar coffee.
But I had already crossed the awkward part.
So I walked up.
“Sir, can I get a discount on the coffee?” I asked the owner.
He looked up from his phone, scratched his cheek, and checked the bill.
Two hundred rupees.
He made a small change and handed it back.
Ten percent off.
I walked back to my table.
Not impressed.
Not proud.
Just… surprised.
It worked.
After that, I started asking more.
Sometimes it worked. Sometimes it didn’t.
But at least I had the satisfaction of trying.
At the café, I asked again.
And again.
Within a month, I had saved a decent amount — just on coffee.
But more importantly, something had shifted.
The hesitation was gone.
So I went back to that deal.
This time, I asked for a better offer.
And this time…he agreed.
I made an extra 1000$ .
Small asks don’t change your life.
They change your willingness to ask for bigger ones.
A story from my upcoming book, Quiet Clarity
Stories That Linger - Character-Driven Fiction
Genres: General Fiction / Contemporary Fiction, General Fiction / Literary Fiction, and General Fiction / Uplifting Literature
Download before the offer vanishes.
If you love rom-com, you can’t miss this amazing book by Cassie Meadows.
