5 lessons from walking together for 3 years

July 2022. First walk. Eight people showed up.

We had no idea what would happen next.

Three years later: 400+ walks. 17,000+ people. Multiple cities across the world.

The numbers are wild. But they're not the real magic here.

The lessons are.

Not lessons we planned to teach. Not insights we mapped out in advance. Just truths that revealed themselves when we kept showing up, week after week, Saturday after Saturday.

Some came from strangers who became friends. Some from conversations that changed lives. Some from moments so small they'd be easy to miss.

But after three years of walking five miles every single week, patterns emerge. Truths surface. Lessons stick.

Here are five things the trail taught us.

LESSON 1: Serendipity Rewards Showing Up 🦋✨

When you show up, luck shows up to greet you.

Rose was in Austin for work. She'd seen the walks online and thought, why not? She had a free Saturday morning anyway.

It was Walk #80. And 8 just happened to be her favorite number.

She met Anthony during the walk. They got to talking and realized something wild: they were from the same exact hometown! Both had moved to Austin three years ago. And this was the first walk for both of them.

After the walk ended, Rose headed to lunch by herself. The host seated her at a table.

It was table #8.

She said it best: "I don't believe in coincidence – just miracles. This walk was definitely one of them."

Here's what we've noticed after three years: this kind of thing happens all the time.

Someone meets their future co-founder on a random Saturday. Someone runs into their college roommate they lost touch with five years ago. Someone gets the exact advice they needed from a stranger who lived through that exact situation.

You can't plan serendipity. But you can show up and create the conditions for it to find you. 🦋✨

LESSON 2: It's Not About the Place, It's About the People 🤝

Home isn't a location. It's the people you're with.

Upasna has been in Austin for ten years.

For most of that time, she loved it. The charm, the quirkiness, the beauty that made Austin feel special. All the reasons she moved here in the first place.

But over the last few years, something shifted.

The city started losing what made it unique. The charm she fell in love with was fading. The quirkiness that made Austin feel different was disappearing, as green spaces turned to concrete and local businesses shuttered their doors.

She watched home change into something she didn't recognize, and she became bitter about it.

Then she found the walks.

Her words: "These walks have made me fall in love with my adopted home all over again because they cultivate community with so much intention. The old school Austin way that I fell in love with a decade ago."

Upasna didn't fall back in love with Austin. She fell in love with the people in Austin who cared about the same things she did.

Cities change. That's inevitable. What we're really craving is intentional community. And that can exist anywhere.

LESSON 3: Making Friends as an Adult Doesn't Have to Be So Hard 🫂

Making friends as an adult feels impossible, but it's actually just about creating the right conditions.

Paris came to a walk with her boyfriend. They both had separate conversations throughout the five miles.

Afterward, they compared notes. Turns out, they'd both really enjoyed talking to the same person.

Her words: "We made a friend! It's really hard to make friends as an adult. The way the walk is set up allows for meaningful connection. My boyfriend and I separately had good convos on the walk... turns out we really enjoyed talking to the same person. We've now hung out with him and his girlfriend multiple times!"

They didn't just make individual friends. They made “couple friends.” Which is somehow even harder than making solo friends as an adult.

Here's why it worked: People show up as themselves, not the polished version they bring to networking events. There's no performing. No draining work talk. You're going deep into real topics from the start.

When you skip "what do you do?" and talk about what actually matters, you see who someone really is. And when you're walking side by side talking about real things, you get a quick vibe check on the person that doesn’t require meeting for a coffee on a random Tuesday morning.

If you're lucky, you hit it off with at least some people. It happens more often than you'd think.

Making friends as an adult isn't hard because people are closed off. It's hard because most social spaces don't create the conditions for real connection.

LESSON 4: We Transform in the Presence of Curious, Kind, and Open-Minded People 🐛🦋

The right environment doesn't just connect people. It transforms them.

Over three years, we've watched it happen again and again.

A woman in her 30s quit her corporate burnout job and became a private chef. She found her first clients through people she met on the walks.

Two strangers bonded over infertility during a walk. Both are now moms. And best friends.

A socially anxious man who hadn't attended an event in over a year became a beloved regular. Now he leads the post-walk brunch hangouts.

Someone who attended 50+ walks completely reinvented himself while walking. Sold his company for seven figures.

On a recent walk, our London host Cristina had a surprise influx of gratitude. One woman shared how the walks helped her grow the confidence and courage to finally take a drama class she'd been wanting to do for ages. Just to explore, to play, to try something new.

These aren't isolated stories. They're the pattern.

When you put curious, kind, and open-minded people together… something shifts.

Not because anyone's giving advice or trying to fix you. But because you're finally in a space where you can think out loud without fear of judgment.

Where people ask questions that help you see yourself clearly. Where you're surrounded by people who believe growth is possible.

Transformation doesn't happen in isolation. It happens in spaces where you feel safe to be yourself.

LESSON 5: Real Connection Doesn't Need Substances 💞

The best conversations happen on the trail, not at the bar.

Shyanne said it perfectly: "I feel energized around good, wholesome people and having deep conversations. It can be difficult at times finding a way to socialize and make genuine connections without substances beyond a hot cup of coffee being involved…"

She's not alone in that struggle.

Most adult socializing revolves around alcohol. Happy hours. Wine nights. Bar meetups. And if you don't drink? Your options for connection shrink dramatically.

The walks prove you don't need it. AM on a Saturday. Walking five miles. Talking about what actually matters.

No liquid courage required.

Sure, alcohol lowers inhibitions and nerves… but it also numbs presence.

On the walks, people are fully present. Fully aware. Fully themselves.

The vulnerability comes from safety, not substances. The energy comes from connection, not cocktails.

And when you meet someone sober you know the connection is real.

The relationships you build are based on actual compatibility, not just a shared buzz.

What’s Next 🥳

These five lessons came from three years of showing up.

Serendipity that rewards presence. Community over geography. Friendships that form faster than you think. Transformation in the right environment. Real connection without substances.

But the regulars keep asking: "What about the other 166 hours in the week?"

Saturday mornings proved meaningful connection is possible. Once you've tasted it, you want more.

So we've been building our next adventure: a premium global community that brings the magic online. Year-round connection with people who get it.

If your soul is whispering (or screaming) YES to this, join the waitlist to be first to know.