There are 3 Paths You Can Go By - Part 2: Going on a Quest
Eventually, I shifted from chasing a single, all-defining purpose to pursuing a set of “Top 10” lifetime goals.
It felt more manageable. More actionable.
But I quickly ran into a familiar problem.
I became fixated on one of those goals: finding a real-world version of Rivendell. And once again, it started to turn into a kind of purpose trap—hard to define, slightly escapist, always just out of reach.
Still, something important happened along the way.
That search opened the door to deeper conversations with a close friend—about spirituality, meaning, and questions I had been avoiding. I started reading new thinkers, attending workshops, and eventually enrolled in a year-long coaching program. That experience changed how I saw myself and my life.
Around the same time, I discovered Esalen in Big Sur. When I visited, I remember thinking: this might be the closest thing to Rivendell I’ll find. It even inspired a business idea—creating a kind of “mini-Esalen” in the city. A friend and I seriously explored it, imagining leaving our corporate jobs.
We never launched it. But the process itself was fun and mattered.
Then came another turning point: discovering Your Money or Your Life. Financial independence became my next major quest—and this time, I followed through.
Ironically, even that didn’t “end.” It evolved into a way of living: habits, systems, and ongoing awareness of whether my spending aligned with my values.
That’s when I started to see the pattern.
Big goals—quests—can be powerful. But they can also become what some call the “Grand Goal Theory”: the belief that achieving one major goal will finally resolve everything.
It rarely does.
Without the right lifestyle underneath, even the biggest wins can feel… incomplete.
I still believe in quests. But now I see them differently.
In the next post, I’ll explore what actually supports them.
In the meantime:
What big goal are you chasing right now?
And if you achieved it—would it truly be enough?