You know those conversations where you walk away feeling heavy?
Not because the topic was super complex, but because the other person wasn't actually listening. They were just waiting for their turn to talk. Building their rebuttal while you were mid-sentence. Defending their position instead of exploring yours.
You leave feeling exhausted. Like you just spent an hour pushing a boulder uphill.
Now imagine the opposite: a conversation where someone asks why you think what you think. Where disagreement feels like curiosity instead of combat. Where you leave with new ideas you didn't walk in with.
This week, one of our Austin regulars told us about two book clubs. One drains him. The other energizes him. Same format, completely different energy.
The difference? Whether people show up to win or show up to discover.
That's what we're creating on these walks: the second kind of conversation.
Thanks for being here. 🧡
Photos from our walk chapters, happening weekly around the world:
Walk #1 in Detroit, Michigan (January 2026)
Walk #182 in Austin, Texas (January 2026)
Walk #1 in Boston, Massachusetts (January 2026)
Walk #120 in San Francisco, California (January 2026)
(I’d share more, but that’d make this email longer than Infinite Jest!)
🏆 Shoutout to our brave hosts and regulars* in Denver, Columbus, Boston and Detroit for showing up to walk 5 miles in freezing temperatures. One person in Boston said: "I didn't even feel the cold anymore after all the walking and good conversations!”
🏆 Shoutout to Kenji Fullwood and the Denver crew for creating such a welcoming vibe that a new walker said: "I was so relieved to meet a non-judgmental group of people who are truly open to hearing different perspectives. It really brought down that wall." That's the energy. 🧡
🏆 One Detroit member said he loves the walk because he can have deeper conversations with women without them asking “Are you gonna call me?” afterwards. (Watch out for Mr. Steal Your Girl on the trail.)
*Regular = someone who attends multiple walks. Interchangeable with the word “legend.”
Want better conversations everywhere?
This piece walks through the shift that turns debate into discovery.
This is what we practice every Saturday, and it works in book clubs, happy hours, and dinner tables too.
(Spoiler: It's not about the topic! I've seen people have energizing conversations about death, divorce, and debt… and exhausting ones about travel and hobbies.)
Five conversation starters from the walks
Borrow these for your next hang or happy hour!
"What do you wish someone asked you more often?"
"How do you allow an emotion to arise without letting it take over?"
"What makes you feel 'wealthy'?”
"What's a recent moment that made you feel alive?"
"What does friendship look like for you?"
What’s happening in The Board Walks universe
Three people from California applied to host this week. 👀 If you’ve been thinking about it, shoot your shot.
We want to feature you! Got a story from the walks? Submit it here.
Find your walk: Join your city’s Meetup here (or send to a friend who needs this magic in their life.)
Current Cities: NYC, London, Austin, San Francisco, Denver, Columbus, Detroit, Boston, Atlanta, Boone (NC)
The Board: If the walks are the spark, this is the fire.
After hearing the book club story, I started asking myself one question before every tough conversation:
Am I trying to be right, or am I trying to understand?
That's it. One question, and it changes everything.
When I'm trying to be right, I'm half-listening. I'm building my rebuttal while they're talking. I'm scanning for the weak point in their logic so I can swoop in with "Well, actually." I walk away having proven my point… and learned nothing.
When I'm trying to understand, I'm fully present. I'm asking why they see it that way. I'm getting curious about what experiences shaped their perspective. I'm noticing where our logic diverges and wondering what that reveals. I walk away with new information, even if my opinion hasn't changed.
Same conversation + different intention = different outcome.
How are the Austin regular's two book clubs the same exact format, yet one feels like pushing a boulder uphill and the other feels like moving through water?
Because of the shared intention running underneath each one: Are we here to win, or are we here to discover?
The best part: You get to choose. Every time.
You can't control how other people show up, but you can control what you bring to the table. And here's what I’ve learned from 400+ walks: When one person shows up with genuine curiosity, it shifts the energy of the entire event OR attracts like-minded people straight to them.
So before your next hard conversation — with your partner, your boss, your friend, your parent, or a complete stranger — pause for two seconds and ask yourself: Am I trying to be right, or am I trying to understand?
That pause is the difference between combat and connection.
If you’re curious and excited to explore topics from multiple angles… you’re gonna love this space, and this space is gonna love you right back. Pinky promise.
We’ll see you out there. 🧡
Have a whimsical week,
Founder of The Board Walks
P.s. If you know someone stuck in the first kind of book club, forward this their way. 👀
