The Oregon Trail
As a child my family would frequently visit relatives in New York. The "Empire City" captivated me with its towering skyscrapers, hot dogs and pretzels, Broadway, and of course, the Yankees. Coming from the quaint town of Portland, Oregon, the Big Apple felt like the center of the universe. On my return trips home I always wondered why my parents left such a mecca for the sleepy confines of the Pacific Northwest.
For the life of me, I couldn’t see the appeal of a tiny hamlet like Portland compared with the glitz and glamour of New York. The “Rose City” was a place for hippies and lumberjacks, and I didn’t plan on becoming either. When you’d mention Portland to a New Yorker their response was always the same - a shoulder shrug of indifference.
Still, I eventually grew to love my hometown with its majestic beauty and art-inspired culture. While Portland will never be confused with New York, it certainly holds its own these days. But it isn’t the food trucks, Powell’s Books, or the hipsters that make 'Portlandia' great, it’s the spirit of the place - The rugged sense of adventure and the willingness to explore what moves us on the inside by changing our circumstances on the outside. That spirit is woven in to the fabric of the Pacific NW dating back to the most famous thing to ever occur there – the Oregon Trail.
The Oregon Trail isn’t just an old dirt road talked about in history books or a cheesy 80s computer game, it’s a quest and an energy that lives on to this day. Many risked their lives and livelihoods exploring our nation’s final frontier. While some sought to stake a claim on cheap land and others simply wanted a rush of adventure, those that braved the trail all shared a common theme – leaving the old to discover the new.
This sense of uncovering and unearthing our destiny is our ultimate task spiritually, emotionally and professionally. Nike founder Phil Knight referenced this spirit in his compelling biography Shoe Dog. Knight’s famous college running coach and mentor Bill Bowerman frequently used the Oregon Trail lore in an effort to inspire his runners like Knight and the legendary Steve Prefontaine. “The cowards never started, and the weak died along the way. That leaves us,” Bowerman would say.
Says Knight, “Some rare strain of pioneer spirit was discovered along that trail, my teacher believed, some outsized sense of possibility mixed with a diminished capacity for pessimism – and it was our job as Oregonians to keep that strain alive.” The sentiment struck a chord with Knight inspiring him not only to run faster, but also to pursue a new way to express how we play. In doing so, Knight and Bowerman changed the world of running, sport, fashion, and culture.
In describing his own quest Knight explained, “Deep down I was searching for something else, something more. I had an aching sense that our time is short, shorter than we ever know, short as a morning run, and I wanted mine to be meaningful. And purposeful. And creative. And important. Above all…different. I wanted to leave a mark on the world. I wanted to win. No, that’s not right. I simply didn’t want to lose.” It wasn’t dumb luck, playing the game, or even hard work that propelled Nike to one of the biggest brands in history but belief, optimism, and the resolve to chart a new course.
Though a New Yorker by birth, My Dad (also named Phil) is an Oregonian in spirit. Like millions before them, my parents blazed their own trail back in the day, renting a small U-Haul and making the trek across the country to start a family and new life among the Doug fir trees and the peaceniks. They missed the food and the energy of Manhattan, but they never looked back. The trail was out there in front of them.
While New York personifies the traditional pinnacle of success and the height of commerce and culture, the Oregon Trail represents a different narrative - Bigger, better, and louder isn’t the metric of success, purpose and authenticity are. Success on ‘the trail’ isn’t about climbing the ladder, but about displaying courage and risking it all to discover your true destiny.
Like the two Phil’s, my aspiration has long been to have enough fortitude to trade the known world for purpose and meaning. My dream is to live a life that manifests the qualities of serenity, peace, and creativity. I imagine an open sky and pray for an open mind. On my quest, I’ve tried my hand at being a salesperson, dot-comer, and actor, a trainer, manager, and a writer. I’ve lived downtown, uptown and in the suburbs. I’ve tried the mountains, the city, and the ocean.
What I’ve learned is that it isn’t the vocation or the location that matters, but grit and the willingness to wrestle with the important questions of the day. Thankfully, I’m not alone on the journey as faith, family and friends are constant companions. I not only possess the support of those close to me, but when the trail seems particularly daunting, lonely and treacherous, I have the courageous examples of others right beside me -
· My best friend faced the biggest trauma of his life by reinventing himself and finding the courage to pursue his true calling as an actor. He’s now the artistic director of a theater company.
· A former colleague of mine left her long and successful career in fitness to go back to school and pursue her life long dream of living in Paris where she now resides.
· One of my childhood friends recently moved to the Mojave desert to live off the grid, open a music studio, ironically leaving Oregon to do so.
The Oregon Trail isn’t about Oregon being an answer any more than it’s about New York symbolizing a status quo to leave behind. The grass isn’t any greener in Oregon (actually it is, but you know what I mean!) than in New York. The meaning of life isn’t found in a new place and you can’t simply leave your problems behind by changing addresses. What matters is facing adversity, the ability to adapt, and the resolve to change courses when you’ve lost your way. For that matter, true satisfaction and bliss can be found without ever leaving home...But I’ll take my chances out here on the trail.
The Oregon Trail is a metaphor for life and we all have the capacity to be frontiersmen and women and explore the boundaries of possibility and wonder. Brené Brown calls this quest Daring Greatly. Another author described the trail metaphor in this way: “Life is full of distractions. It's full of people telling you can't cross mountains and can't achieve your dreams. It's full of disease. It's full of people you love getting sick...It's full of mistakes, miscalculations, and missed opportunities. It's confusing and too short and too long.”
Life is worth living and truly doing so means risking disappointment and heartbreak. Choosing the trail is about confronting the nagging questions, pursuing callings and passions, and most of all, the willingness to fail. I’m still in the covered wagon crossing the rugged mountains and barren plains, but my heart is open and my spirit is full of hope and wonder.