Explorer's Side Quest

Adventure, good people and a world that invites you to play. Along the way, aliveness, the emerging energy that moves through you when an idea or a moment feels exciting and true to you, recalibrates the game you're playing.

A small group holding hands at Machu Picchu as the sun crests the mountains

The game of life, played somewhere new

An Explorer's Side Quest is a small-group adventure somewhere in the world worth the journey. Days on the trail, meals that run long and conversations that go wherever they want to go.

Everyone who comes is playing their own game of life. The Side Quest gives that game room. The experience itself does the work: what feels alive rises to the surface and quietly shapes the game you get to design next.

It's fun on purpose. Play is how the recalibration happens.

The Sacred Valley, Peru, green terraces under a big sky

Your edge, then rest

Every Side Quest carries some challenge, and the challenge changes with the place. It might be twelve days on foot at altitude. It might be one early climb with comfort and good food on either side.

Meeting your edge is how you learn where it is. Now and then you step past it. That knowing travels home with you, into the life you've designed.

Stress plus rest equals growth, the same way a muscle grows. So rest is part of the design: slow afternoons along the way and, for anyone whose schedule allows, a few quiet days afterward to let it all settle.

Simple places have a way of resetting things. A hot shower feels like a gift. Ginger tea after a long climb tastes like a feast. You come home seeing your own comforts fresh.

Lane standing above the valley at Machu Picchu

Who you'll be exploring with

Small groups of people who love adventure and good company. Entrepreneurs, creators and builders of all kinds.

Everyone brings different gifts, different experience and different expertise, and finding out what those are is half the fun. The way one person plays their game often holds exactly the idea someone else needed, in business, relationships, the body and the craft of living well.

Some of the best conversations of my year happened on a trail.

The September 2025 Peru group at Machu Picchu with Huayna Picchu behind them

Held by people who know the ground

Every Side Quest runs with local partners who know their ground. They carry the route, the pacing and the logistics, so you get to be fully present. There's a particular freedom in being held by a structure that experienced hands built.

Where they go

Peru has hosted these gatherings since 2019: the Sacred Valley, Lake Titicaca and Machu Picchu.

Terraced fields above Lake Titicaca, Peru
Lane on a four-wheeler in the highlands of Peru

Nepal is calling too. If the Everest Base Camp story brought you here, I'm open to gathering a group trek with Wangda and his team at Trekker Nepal once enough people raise a hand.

When a trip takes shape, it gets its own page with the full itinerary.

A small group of trekkers at the Everest Base Camp rock, 5,364 meters
The group at sunrise on top of Kala Patthar with Mount Everest behind them
Trekkers with headlamps climbing toward Kala Patthar before dawn under the stars
The group climbing stone steps beside a waterfall on the Everest Base Camp trail
Questions

Common questions

A small-group adventure somewhere in the world worth the journey, with good people and some challenge built in. Everyone comes playing their own game of life, and along the way the experience and the aliveness it stirs recalibrate that game.

Entrepreneurs, creators and people who love adventure, exploration and good company. Groups stay small. Everyone brings different gifts, experience and expertise, and the exchange between them is a big part of the trip.

It depends on the trip. Some carry real physical challenge, like a multi-day trek at altitude. Others weave comfort and beautiful places to stay around one demanding day. Each trip's page describes its own challenge, and rest is built into every one.

Past Side Quests have run in the Sacred Valley, Lake Titicaca and Machu Picchu in Peru. A group trek to Everest Base Camp with Trekker Nepal can come together if enough people raise a hand. The next one is forming now.

Send a note through the form on this page about the kind of adventure that feels alive for you, and I'll write back. Tick the box if you'd like first word when a Side Quest forms, along with the other things I share.

What adventure is your life waiting for you to say yes to?

Tell me in a few lines. I read every note and I'll write back.