Hi Reader,

Thanks for being here.

I love you almost as much as the new pickleball paddle I got this week.

I am now more paddle than player.

Look good play good am I right?

Unlock a Bolder Version of Yourself ⚡️

My first 14-day group challenge just wrapped up this week.

It was all about being BOLD and asking strangers for funny & outrageous things.

Here's what people are saying about the experience:

"I know this challenge will have a significant impact on my entire life. I can't believe I've never done something like this before."

“This challenge helped me see just how much opportunity is available to me when I can step into a little bit of courage. It exposed me to some really cool moments with strangers full of joy, laughter, support, kindness, curiosity, and playfulness."

"Gregory holds space for others in such a loving way while challenging you to tap into your boldest self!”

Here's the good news:

I am launching another FREE 14-day Challenge!

It is going to start on Wednesday.

If you're looking to transform your life through BOLD action, come join us.

You can expect:

  • 1:1 time with yours truly
  • A digital guide on how to Live a Story Worth Telling
  • Group calls
  • A life-changing experience

Click the button below to sign up:

P.S. I'm keeping the group small so everyone gets deep, personalized attention.

Join ASAP - there are only a few spots left!

What I'm learning 🧠

That the world is a very small place.

I believe that the Universe rewards bold action.

This belief is the very reason that I am subjecting myself to 100 days of being bold and talking to strangers.

Today is day 23 which means I have 77 days left.

That horrifies me.


Because after asking strangers to:

  • Push me on a swingset
  • Let me cannonball in their swimming pool
  • Read out loud to me
  • Sing happy birthday to my friend
  • Give me a piggyback ride

And so many more outrageous ideas, I still get really scared.

Pushing yourself out of your comfort zone day after day is tough.

There have been so many days when I don't feel like talking to anyone.

When the thought of simply smiling at a stranger feels impossible.

But I continue because I made a commitment to myself.

And the more I lean in, the more the chips are falling into place.

I was on the phone this past week with a new friend.

I was telling him what I was up to when he said, "You need to meet my roommate."

It turns out that his roommate makes bold requests of strangers for a living.

He has a YouTube channel called Discover Connection and I highly recommend you check it out.

But get how crazy this is.

Just one week before, my friend had sent me Discover Connection and said it was one of his favorite YouTube channels of all time.

I went from never having heard of it to potentially getting to meet the creator of it in less than a week.

When coincidences like this happen, it feels like magic.

It feels like the Universe is rewarding me for being bold and facing my fears.

So I'm going to keep going.

It's a small world we live in, and each day I'm getting to meet another person in it!

Quote of the week 📜

“Always laugh when you can. It is cheap medicine.”

- Lord Byron

What I'm listening to 🎧

I went on The ManKind Podcast this past week to talk about my journey!

Check out the episode by clicking the link below:

100 Days Of Living Boldly & Talking To Strangers with Gregory Benedikt

We are going to record another episode at 50 days and a final at 100!

Hope you enjoy :)

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Sent with love,

Gregory Russell Benedikt

Talk to me: hello@gregoryrussellbenedikt.com

Website: gregoryrussellbenedikt.com

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 https://bit.ly/3zMgtyD. If that's too much right now, drop your email below to start loving your Monday mornings.

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