Gregory Russell Benedikt

Last Week I Asked a Stranger to Cannonball in His Swimming Pool

Published 6 months ago • 2 min read

Hi Reader,

My inbox has been flooded with requests for more dad jokes.

I'm no comedian, but I can't help but give the people what they want.

I wanted to tell one about airplanes, but it'd probably go over your head.

Then I thought about my best construction joke, but I'm still working on it.

So I will settle with a question.

The other night I went to a restaurant with my girlfriend.

It had excellent food but no atmosphere.

Can you guess where it was?

The moon!

What I'm learning/thinking about 🧠

The things strangers will say yes to with little context.

It has been a wild week to say the least.

I learned that Whole Foods does not have a Gregory discount on groceries but (some) strangers will let you swim in their pool.

I have completed 6 days of asking strangers for ridiculous things and have been surprised by what people are willing to say yes to.

Below is my favorite story of the week.


Standing there in my boardshorts holding my towel, I felt ridiculous.

At the same time, I also felt like a little kid again.

My heart pounded as I channeled my inner 7-year-old.

I reminded myself that nobody would mind if a child asked for a quick swim.

But I haven't been a child since 2001.

I am a 28-year-old man with a magnificent mustache.

The voice in my head was screaming at me that this was a terrible idea.

I was about to run away when suddenly the door opened...

I put on my best smile and said:

"Hi I'm Gregory and I was wondering if I could cannonball in your pool?"

First I was met with silence.

Then, the hint of a smile and a confused laugh.

"Ummm....sure....but why?"

It's inspiring to see what strangers will say yes to with zero context.

Not only did this man say yes, but he filmed me executing a perfect cannonball.

This was day 5 of 100 days of asking strangers for outrageous things.

I am doing this to face my fear of rejection and live a story worth telling.

So far both goals are being hit.

But the best part is the unintended side-effects.

All of the strangers I have made requests to have left our interaction with big smiles on their faces.

This might be the most ridiculous way to make a positive impact, but it's making my palms sweat and bringing a 7-year-old child-like grin to my face.

P.S. You can watch the video of this on my Instagram by clicking here.

Quote of the week 📜

"Excitement is a better motivator than discipline. The people who appear to have an exceptional work ethic or remarkable discipline are often those with a genuine curiosity or interest in that area. The person who smiles is more likely to keep working than the person gritting their teeth."

- James Clear

What I'm reading 📚

The bible of asking strangers for bizarre things.

Rejection Proof by Jia Jiang.

My 100 days of (attempted) rejections were inspired by this book and it's a must-read for anyone looking to live an extraordinary life.

If the thought of making 14 bold requests of strangers across 14 days sounds exciting, join my FREE group challenge I am launching this Friday.

Click the link above to start living a story worth telling and become rejection-proof.

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Sent with lots of love,

Gregory Russell Benedikt

Talk to me:


Writing: Medium

Connect: Instagram & LinkedIn

Gregory Russell Benedikt

I am on a mission to have 100 conversations with people about their biggest dreams. Book your free Dream Session at If that's too much right now, drop your email below to start loving your Monday mornings.

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