Jeremy N. Smith

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June 18, 2026

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Dear friends,

Late last month, a dozen people from across the country met in Missoula for my two-day, retreat-style “Breakthrough to Brave” workshop.

There was laughing, crying, coaching, connecting, dreaming big, and taking action.

Between day one and two, everyone had the same homework assignment:

Get three Nos.

***

The Nos could be in person, on the phone, via text, email, or any other way—and the encouragement was to get as many as possible in person.

They had to be real asks—i.e., you couldn’t tell someone that you wanted them to say no, or “This is just an exercise.”

Stay in the game and see what happens, my instructions concluded.

The first thing we’ll do tomorrow morning is share stories and compare learnings of how it went.

***

The group succeeded in failing.

Here are three Nos people got, for example:

  • (in line at a cafe) “Can I pay for your coffee?”

  • (at a hotel front desk) “Can I check guests in?”

  • (1-on-1) “Will you get a tattoo with me?”

But they also got at least as many Yeses:

  • (to a guy met 48 hours earlier) “Will you take me out to dinner tonight?”

  • (to a bartender) “Will you charge me 1 cent for my drinks?”

  • (to a musician on break at a concert) “Will you play one of these five songs—and invite me on stage to sing it with you?”

The world wants to love us, treat us, and play with us, it turns out.

The people we think we might be bothering?

They like being surprised—and, when they can, they love saying yes.

It was a wake-up call that I could NOT have this anxiety of what ifs—and I won’t because it won’t work, one participant wrote me afterwards.

It scared me more to feel scared for the next 20 years than actually being scared scares me.

Another put it this way:

Biggest shift: The twin feelings of “Whoa, this could be played way bigger!” and “Wow, I’m playing really big already!” sitting together on a porch swing, trusting that they both belong.

***

You can run this same experiment with friends and family.

Recruit three to twelve people.

Explain the rules of the game.

Give them from 5:30 p.m. Saturday to 10 a.m. Sunday to get three Nos.

Gather then and share stories.

At the end, ask each participant:

  • What’s one thing you learned about yourself?

  • What’s one thing you learned about other people?

  • What’s one thing you learned about the world?

And let the brave wisdom flow.

***

Write me if you do this—I’d love to hear your takeaways.

Or reply to this message if you’re intrigued but want additional clarification or support.

Regardless, know that I’m rooting for you, and cheering each Yes and No.

We only get those answers if we dare to ask.

And asking is a gift to other people.

Look at the above examples—and the receipt below.

Each request we make offers respect, acknowledgement, entertainment, inspiration, opportunity, curiosity, possibility, or collaboration.

The only way to lose this game is not to play.

Go for the no—

Jeremy

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