Hi, I’m Tait.
I grew up in a small town in Montana. A place where the forest and rivers were my backyard, and adventure was less of a hobby and more of a rite of passage. A place where you either learned to handle solitude or let it eat at you.
Most of my best memories — and hardest lessons — happened alone out there.
Falling into a tree well in eighth grade.
Floating in pitch black November water after my sailboat capsized on Ennis Lake, thinking for the first time: “I might not make it.”
Or winter camping solo in a full-on blizzard the night before senior prom.
The spark’s always been there. I just didn’t always know what to do with it.
Truth is, I’ve never been good at being comfortable.
I’ve tried it — the easy path, the ordinary rhythm.
Something in me withers when life gets soft or boring.
When I’m not chasing something. When I’m not building something.
When I’m not daring something.
This site is part logbook, part lighthouse. It’s for me — the version of me who, years ago, looked out at a big, wild world and wondered if there was room for someone like me in it. Someone with ambition too big for their small-town zip code, and dreams that felt both thrilling and terrifying.
It’s also for you — if you’ve ever felt that too.
What You’ll Find Here
This isn’t a travel blog.
It’s not about bucket lists or bragging rights.
It’s about choosing the long roads in life — the ones that cost more, ask more, and make more of you.
We’ll find stories. Failures.
Reflections from the road, the saddle, the sea.
And letters — to my younger self, to strangers, to the person I’m still becoming.
Because I believe in telling the story while it’s still being lived.
Not once it’s safe or finished.
This isn’t about proving anything.
It’s about remembering who I am — and leaving something behind that might help someone else do the same.
If you’re out there wondering whether you’re too late, too early, too small, or too far off…
You’re not.
You’re right on time.
And the world is still waiting.
Tait Olson 