3 Surprising Lessons I Learned From Spending 100 Days Getting Rejected By Strangers

And how I ended up in a stranger’s swimming pool

Gregory Russell Benedikt
7 min readApr 23, 2024
The surprisingly kind (and responsible) Amazon delivery driver who didn’t let me drive his truck

My heart pounded as I knocked on the stranger’s door in front of me. I was wearing a swimsuit and holding a beach towel and I felt ridiculous.

At the same time, I also felt like a little kid again. I tried to quiet my mind and channel my inner 7-year-old but I was quickly losing my mental battle. I switched tactics and tried to reassure myself that no one would mind if a child knocked on their door and asked to use their swimming pool. But I hadn’t been a child in over 20 years. I was a 29-year-old man with a magnificent mustache.

The voice in my head screamed at me that this was a terrible idea. I was about to turn and run away when the door opened. Suddenly, I felt like I was in a nightmare. I put on my best smile and said:

“Hi! My name is Gregory and I was wondering if I could cannonball in your swimming pool?”

A shocking response

Time slowed down as the man who opened the door stared back at me. He was silent for what felt like an entire minute. Then, he suddenly burst into laughter. With a smile on his face, he said…