The SideQuest Begins
Elevate. Endure. Evolve. ⚔️ Find meaning through motion.
People who know me well, will tell you I’m not great at sitting still.
I’ve always got something going on, some project or another. I’ve always been a seeker.
Of what, you may ask? I’ll tell you when I figure it out.
I often joke about that old U2 song; it’s truth for me, and maybe that’s why it’s always been close to my heart. But we all know, behind every joke is at least half a truth.
As I get a bit longer in the tooth, I think I’m realizing the old adage is right: the journey is the destination. Maybe that’s what I’m in love with, not some far-off Shangri-La, but the search for it, and all the people and places that come along the way.
So I thought, why not make it a bit more official?
The SideQuest isn’t about starting something new for the sake of it. It’s about giving structure to something I already do and already need.
Some heady concoction of travel, exertion, and exploration.
Endurance training, the long runs, the climbs, the hours outside, it’s the one space where I can actually hear myself think. It clears my head in a way nothing else does. It’s my meditation.
I’m not the best, the fastest, or even really competing (except maybe with myself).
Rather, in my own way, I’m finding peace.
If I’m going to keep doing it anyway, I may as well turn it into something meaningful, share it, and maybe make it useful for other people, maybe inspire you to find your own SideQuest.
Or at minimum, entertain you if you’ve made it this far.
What is The SideQuest?
It’s not a race.
It’s not a midlife crisis.
It’s not really a hobby either.
It’s a framework for doing hard, interesting things on purpose.
A series of ongoing quests, physical, creative, and mental, that live alongside the main story of life and work.
The next one happens to be a bit of an adventure in Europe: a 309 km (about 192 miles) traverse of the Swiss Alps in the summer of 2026. More to come on that soon.
I’m thinking I’ll try to do it in four-ish days.
Why? Like most of the interesting things in life, it spun out of something more ordinary.
I recently launched a business with my co-founder, Chid Liberty, called Apprentos (https://www.apprentos.com). We’re working hard to revolutionize the registered apprenticeship landscape in the U.S.
As fate would have it, the gold standard for apprenticeship systems happens to be Switzerland.
The more time I spent there, studying and learning how their system works, the more I fell in love with the landscape.
It felt fitting to map a journey across it, to understand it in a deeper way.
And so it begins.
But there will be others.
This isn’t a single quest; it’s a lifelong project, to lean into the unknown, physically, mentally, and spiritually, and to explore where curiosity, endurance, and (hopefully) enlightenment intersect with purpose.
Why The SideQuest Exists
On another SideQuest, while at Oxford reading for my Executive MBA, Professor Kurt April talked about the difference between importance and significance.
Importance is about recognition.
Significance is about meaning.
That idea stuck with me.
Most of my career, and to date, many of my aspirations have lived on the side of importance, the measurable kind of success.
But there’s another kind that doesn’t show up on spreadsheets.
Or, if I’m being honest, in places like this.
Or in Instagram reels, or anything of the sort.
It’s the kind that comes from effort, exhaustion, surrender, and discovery.
The SideQuest is my way of exploring that second half, significance… through motion.
Pixels, Light, and the Space Between
I grew up in a time when video games started as very rudimentary pixel art.
They evolved quickly, but they were still very clearly pixel animations, not remotely life-like.
I remember our first Texas Instruments computer and Space Invaders, and then, just a few short years later, being completely mesmerized by Nintendo and Zelda, how real it felt.
Well, real enough that it stopped being just a “complete the objective” game, taking out the pixels raining down on your spacecraft, and became something that felt close enough to life that it sparked imagination.
What I loved wasn’t necessarily how real the games looked.
It was still obviously a video game.
It was the gap between what you saw and what you imagined.
The worlds were believable but unfinished.
Your mind had to fill in the rest.
In a similar way, I fell in love with black-and-white photography, particularly the work of Ansel Adams and how he used light and exposure to pull the grandeur out of real landscapes.
Those images didn’t create fantasy.
They revealed truth.
Somewhere between those two things, the roughly framed and imagined, and the evocatively captured and elevated, is the space I enter when I run through different places.
The real world around me and the imagined world in my head blur together.
A run through a foggy forest feels like a portal could reveal itself at any moment.
A deer on the trail feels like a messenger.
It stops being training and starts feeling like a Quest.
That’s what I want to share here, that intersection of endurance and imagination, of exhaustion and insight, of the real and the mythic.
The science and the story.
Because in the middle of all that, if you’re open to it, I think you, like me, might find meaning.
What You’ll Find Here (and on Instagram @thesidequest.io)
Dispatches: Reflections and stories from training, preparation, travel, and ultimately the Quest itself, particularly focusing on the mental side of all this, the physical prep, the numbers, and the ideas that surface when you spend enough hours alone in motion.
What You’ll Find on my Website (coming soon!)
Labs: Not like bloodwork, but studies and experiments with my biometric data, gear, training and nutrition protocols; what I’m learning about physiology and performance along the way.
Films: Short visual pieces and behind-the-scenes work from upcoming Quests and footage from the actual Quests pieced together into hopefully inspirational and compelling stories.
Partners: Brands and people who align with and support this mission, and believe endurance can be art.
What It’s Really About
It’s not just about training endlessly and running across mountains.
It’s about exploring the world and yourself at the same time.
It’s about curiosity, discipline, and what happens when you do something hard just because you can.
It’s about moving from importance to significance, again, and again… and again.
Thanks for being here.
Subscribe, share, or just follow along.
I’ll post training logs, thoughts, photos, and eventually updates as the Alps 309 Quest gets closer.
But the real story is ongoing.
Every one of us has a SideQuest.
This is mine.
