There's a conversation you haven't had yet.
You know the one.
It's not that you're afraid to have it. It's that you're afraid of what happens after. Once you say the thing out loud, you can't un-know the answer. And part of you isn't ready to know.
So you carry it.
Most people carry it for a long time.
Here's what we've learned after nearly 20,000 people, 15 cities, and thousands of miles of honest conversations: clarity doesn't come from thinking harder. It comes from saying the truth out loud to the right person at the right moment.
Johnathan had been thinking for months.
It took one stranger, five miles, and a single question to end a company… and begin the next chapter of his life. 🧡
Snapshots from our walking villages in cities around the world:
“Everybody dove right in, and showed up super jazzed to dive into deeper topics. They really appreciated that this walk exists.” — Host Brian, from Miami Walk #2
The “Make Friends” mural in the background was not a paid actor. Life imitates art in Atlanta, Georgia.
“We spoke about the costs and rewards of living an authentic life, and that it requires you to disappoint others. To take a stand for your truth. And while this might mean that some people will go, what you gain is so much greater: self-respect and actually living a life on your terms.” — Host Cristina, in London
Smiles from San Francisco. Cherry blossoms are blooming and so are we!
(Don’t see your city? We post the photos in each Meetup group after the walk. Otherwise this email would be longer than a CVS receipt.)
Every week, a few humans in our world do something worth celebrating:
🏆 “I feel like I’ve been in this community for 3 years, and it’s only been 3 weeks.” A regular in Detroit said this to Izzy. That right there is The Walk Effect. Happens everywhere, no matter the city. 🧡
🏆 A walker in London woke up overthinking and almost didn’t join, but she learned that showing up and being present is enough. Shoutout to host Cristina for creating a safe space for people to show up exactly as they are.
🏆 Brian rated his second walk in Miami a 10/10! Friendly, curious humans showed up eager to dive into their topics. The desire for depth is universal.
Johnathan knew his co-founder situation was broken. Every week he stayed, the decision got heavier, because admitting the truth meant grieving the company he thought they were building together.
He showed up to the walk one Saturday, not expecting advice.
Then he met Kurt on mile one.
Kurt was a first-timer. A startup investor. The kind of person who had watched co-founder tension play out enough times to recognize it immediately. He gave Johnathan one piece of advice: ask your co-founder if he’d be willing to see a “marriage counselor for business partners.” If he's open to it, he's open to working things out. If he's not, you have your answer.
Johnathan had the conversation. His co-founder was not willing.
So he quit and never looked back.
"A conversation I had on the walk directly led to me leaving my company and beginning the next phase of my life,” Johnathan shared.
The walk didn't give Johnathan the answer. He already knew it, deep down. The walk just built the runway to ask the question he was avoiding.
This week on The Board Walks, people brought these topics:
"What is something you are silently working on?"
"How do you have hard conversations?"
"What version of yourself are you becoming?"
"Do you believe everything happens for a reason, or is it coincidence?"
“How are you staying grounded right now?"
Screenshot these. Steal with pride. Bring one to your next dinner party to shift the conversation from “meh” to marvelous.
Quick hits:
🎉 Two new chapters are coming!
Madrid, Spain.
Huntington Beach, California.
Know any humans out there who’d love this Saturday morning ritual? Send them our growing community hub; you’ll see all 15 cities and 3.7K members. (We’re growing rapidly. Epic hosts apply every week!)
🔐 The Board opens next week. Our curated global network for people who’ve built a full life but still haven’t found the right room.
Most of the conversations we need to have are living right under the surface.
We just haven't found the right person. The right moment. The right five miles.
Johnathan knew. He just needed a stranger on a walk to ask the question that made the truth impossible to ignore.
This week: what's the conversation you keep almost having?
If you’ve been wondering if it’s time to join us, let this be your sign.
It’s time.
We’re now in 15 cities. Austin. San Francisco. New York City. London. Miami. Columbus. Detroit. Boston. Atlanta. Boone. Sacramento. Denver. Aveiro. And now… Madrid and Huntington Beach!
Looking to become a pillar of your community? Apply to host →
Have a whimsical week,
Founder of The Board Walks
P.s. The Board opens next week. If you've been waiting for the next thing after Saturday mornings, this is it. 🧡
