Here’s to the long roads
The solo climbs, and the stories that shape us
I’m Tait — cyclist, aspiring sailor, builder of things, and student of life. This is my place to document it all: the dirt, the doubt, the wild beauty, and the small truths that keep us going.
If you’re chasing your own version of impossible, you’re in the right place.
Posts
“Life Expands or Shrinks in Proportion to One’s Currage”
-Anais Nin
(Just One of My Favorites)
Why I’m Doing This
Because there’s something about pushing past the line — the fatigue, the wind, the doubt — that sharpens a person. This journey I’m on (including an attempt to circumnavigate solo and nonstop) is bigger than a single goal. It’s about becoming.
I write to remember. I share to connect. I build to earn the future I dream of.
A Few Truths
I rarely know what I’m doing.
I’ve questioned everything, and continue to still
I’m scared of failing — but more scared of not trying.
I am a truly tenacious bastard.
When things fall apart- I adapt.
I’d rather be over the edge chasing something meaningful than shrink into something safe
The Road So Far:
⛰️ 2024 – Solo Self-Supported Ride across the TransAmerica
🌊 2025– First Visions of Circumnavigation
🔧 2025 – Building this site, the brand(s), this idea worth chasing
🚀 2026–2027 – Sailing Prep + Beyond
Tait Olson 