An Entrepreneur's Pilgrimage

My first trip overseas was to hike a 1200-year old pilgrimage across Northern Spain. The Camino de Santiago is a series of winding, sometimes mountainous, sometimes flat, sometimes arid, sometimes lush trails that traverse much of Western Europe but all lead to the Cathedral of Saint James in Santiago de Compostela in Galicia.

My walking partner Christina and I had heard about the trail from the assistant master of our residential college as Northwestern freshman, and immediately began scheming on how to get undergraduate research grants to walk the trail. A year later, there we were, pilgrim's credentials in hand and setting out from St. Jean Pied du Port, a beautiful ancient town nestled in the heart of the Pyrannes just over the French border, and the classical start of the northern route of the 600 mile pilgrimage.

The trip came at an interesting moment for me. I had come to Northwestern University just a couple short years earlier not knowing what to expect, and feeling like I hadn't properly prepared for either the decision or the place it self. My first fall was spent longing for things left in Maine; a girlfriend, a group of friends, and the comfortable lull of knowing the pattern of a place. For the first quarter of my freshman year I was lonely and despondent, uncomfortable with the radical shift.

But then an amazing thing began to happen. The ties back home shifted; the romantic relationship ended, the friends moved on to their own new lives. In my own life, Northwestern was becoming part of me in ways subtle and profound; I began to feel the joy of learning surrounded by smart people; the community of a residential college enveloped me and drew me out of myself, in some ways in spite of myself; without meaning to, I built a new normal, a pattern of goals and experiences that set pace to the seeming chaos around me, and I became comfortable again.

Walking the Camino de Santiago for me was in many ways a celebration of that process that I had been through. By the end of my sophomore year in college I was both physically and emotionally a different person than I had been upon entering. I was proud, for specific accomplishments yes but more for the sense of having built a life (however nurtured the undergraduate life might be) of my own.

Pilgrimage, as I found that year, is fundamentally about leaping. In the 12th century heyday of the Camino, hundreds of thousands of foot travelers came from all around Europe to find the grace that holy relics, in this case the remains of Jesus' apostle James, could bestow. In the heart of Europe's cultural winter, they were seeking transcendence.

Their faith had to be not only in the power of relics, but in their capacity to undertake such a journey. Indeed the power of pilgrimage - and perhaps the power of faith more broadly - is that it is at once about journey and destination, at once about the incommunicable individual experience and almost unfathomable connection to something bigger than oneself.

My explicit aim with the Camino was to research the nature of modern pilgrimage, which is driven at least in the case of the Way of St. James by apparently far more secular aims than it was in it's millennia old hay day. Yet at the same time, my un-communicated purpose - the purpose of the journey itself - was about having the space and time to truly understand what the last two years of my life had meant, and where they led me.

Almost everyone I encountered on the trail had a similar duality. They had their stated "reason" for walking; to lose weight; to celebrate a new retirement; to reconnect with old friends. But then, almost always, they had a deeper reason for walking that felt hidden, and sometimes even hidden to themselves. In many ways, it was the process of slowly revealing to yourself what that reason was that made the experience so powerful.

I write this as I drive across the country on my way to a new city and a new life in San Francisco. After more than a year of planning, I've left the Center for Global Engagement I've built at Northwestern for the last four years to start a new company that hopes to help people unlock the assets all around them to build meaning and value.

The journey is at once exhilarating and exciting. There is something philosophical about the terror of responsibility that the freedom of entrepreneurship creates. As I am the master of my own destiny; so too am I responsible for it's success or failure.

Yet at the same time, many would suggest that this sense of control is an illusion. In a beautiful TED talk, Eat, Pray, Love author Elizabeth Gilbert writes about how before the enlightenment, our conception of genius was not just about the artist or the writer themselves, but about the angels they carried with them. When they were successful, they could not claim success solely for themselves because a little piece of God was with them. Yet at the same time, so too were they liberated from the utter responsibility for the possibility of failure.

As I cross Iowa and Nebraska and Colorado on my way west, the same ground that so many covered wagons crossed in search of something new a century and a half ago, I'm trying to remember what I learned on the Camino. The cathedral to which I've pointed my compass may be the social good and financial reward of a thriving company, but almost inevitably I will end up judging my success by how deeply I experience and remember the mountains and poppy fields and windmills and friends that dot the way.

Photo Credit: Julie Berlin, taken in Boadilla de Camino