When I was finally old enough to undertake my own adventures, there began a long period of trial and error. Mostly error. So many road trips; so many overambitious attempts to realize grand, vague dreams; so many disappointed returns. I sensed that there were great secrets the road could reveal, but for all my trying, I wasn't learning them. The question became: what’s wrong with my recipe?
In 2013, I had just graduated from Whitman, and was in a new partnership with Erin. She had another year of school, so I decided to stick around in Walla Walla while she finished. I'd find an apartment in the fall. In the meantime, Erin was off to northern Minnesota for another summer of guiding canoe trips. My dad had given me the old family van as a graduation gift.
It was time for a road trip.
This one, I told myself, wouldn’t be like past trips. For one thing, I'd do it alone. In the past, I’d always had travel companions, who brought their own ideas of how the trip should go. For another, this one would be longer. Past trips were always too short, I decided, and too structured. This time I'd give myself a whole month, and no itinerary. Wasn’t the whole idea to explore? To learn something new, to expand?
I knew I wanted to go to California, and to try solo backpacking. I envisioned stopping in quirky towns, meeting all kinds of characters, being invited to potlucks and jam sessions. Without plans, I imagined, I would inevitably have the kinds of spontaneous and deep experiences that could awaken a real sense of meaning in my life.
It was a nice impulse, but there were some big pieces missing. I hadn’t really learned how to hang out with myself, so all the time alone in the car and on the trail was draining. I was afraid, it turned out, of the unknown and the unfamiliar, so I stuck mostly to the main routes, the established campgrounds. I remember a morning in southern Oregon: I felt so optimistic as I set out for the day; I poked around, found nice spots by a couple rivers, ate some overpriced fish and chips; by the time the evening was coming on, and I was driving south through the redwoods, not knowing where I would stop for the night, I was feeling depressed. Why am I out here again? It all felt pointless. This pattern repeated itself. I decided that maybe I needed some structure after all, so I started planning a few days ahead, making promises to various friends and relatives that I’d stop and visit. Soon, the spontaneity that had been the heart of the trip’s conception had dissolved.
Though I was dissatisfied with the trip, it was by no means a failure. There were many beautiful moments that I still fondly recall. I did push myself into new, exciting territory, like with the solo backpacking. I did meet people, like the father and his two sons who invited me to join them around their campfire in Big Sur, or the woman I met in Sequoia National Park and hiked twelve miles with, conversing the whole time. And I did have some moments on my own that weren’t lonely and bored but rather deeply peaceful and grounding.
Still, it was nothing like it had been in my imagination. I knew that I had a lot of work to do to get where I wanted to go. I couldn’t shake the nagging feeling that I still hadn’t truly tested my spontaneity hypothesis: that honest flexibility to what might arise can allow travel experiences to transcend their usual limitations.
In the five years since that road trip, I’ve done a lot of work. Or it might be more accurate to say that life has done its work on me. Five years with Erin, and all the lessons one learns in an evolving relationship, have helped me mature. I’ve been in therapy and have come to understand myself and my patterns much better than I did at 22. My 2014 Crohn’s Disease diagnosis woke me up to my own mortality and the urgency of good stewardship of my body. Deciding to pursue professional musicianship has placed me on a path that feels true to my values and my dreams.
Through all that time, my travel experiences have dramatically improved. In 2015, I discovered my love of bicycle touring. My brother Isaac and I rode from Boston up the coast to Portland, then inland across New Hampshire and into Vermont. I was amazed at how many of the problems I’d experienced on past road trips were solved by a simple change of vehicle. My body felt good at the end of each day, and I didn’t get depressed. We saw the landscape from back roads and bike paths, not the interstate; without a windshield between us and the world, we were actually in the places we were moving through. Meeting people happened naturally. They were curious about our strange gear, impressed when we told them our plans; or they were bike tourists themselves, and regaled us with their own tales of two-wheeled adventure. In a small town in southern Maine, we met Jamie, a filmmaker and actor, former Seattleite who'd founded the Northwest Film Forum and had seen Nirvana play a record store on the Ave. He invited us to stay with him in his cabin. We hung out all afternoon and evening, got stoned, made curry, talked art and politics.
“It feels like we’re in a movie,” I said to Isaac. “I can’t believe this is actually happening.”
Later that same summer, there was more travel magic. Erin and I drove up into British Columbia to hike the West Coast Trail. Then we showed up on Cortes Island without a plan. In childhood, the island was my family’s vacation spot for ten straight years. Its serenity and beauty, the earthy whimsy of its community, are deep in my heart. Now I had the chance to share this magical place with my partner.
We slept that first night in the car. The next morning, we used the computer at the co-op to post on the Cortes community web page: we’re two young musicians looking for a place to pitch our tent for a while. We can help out with gardening and housework.
Within an hour, we heard from Andy and Danielle. We ended up staying with them for three weeks. We made music together, shared potluck dinners, met a big bunch of their friends, went sailing and fishing, watched their house and fed their cat while they were away. They showed us such kindness and trust. We made other friends on the island in that time, too. We’d go help folks out in their gardens, and they’d feed us afterward. We met a couple of Chicagoans playing ultimate Frisbee, and they had us over for an evening of great wine, oysters taken that day from the beach, and electric conversation and jamming.
These were not just good times. These were dreams coming true. Here were the deep connections I’d striven for in earlier travels. Here were the spontaneous hangs I’d envisioned, charged with that special magic only spontaneity and serendipity can bring.
I was starting to understand the principles. Put yourself out there. Ask for help, and offer it. Start conversations. Be true to the vision of no plans. Find out when and where the events are, the festivals, the pickup Frisbee games, the volunteer opportunities. Show up. This may all seem obvious to some of you, but these were lessons it took me a long time to learn.
I now see that all my early rough draft road trips were necessary. They were experiments, and they led to meaningful results. Certain things worked, and others didn’t. I now see how nearly everything that has happened in my life has helped prepare me for the trip I am now a month into.
And what a trip. Jam sessions, potlucks, spontaneous hangs. Sunsets, bonfires, stargazing. Mushroom hunting, roller skating, Frisbee, ping pong, horseshoes. Farms, gardens, beaches, parks. Meditation, yoga, reflection, writing. So many new friends, so many people opening their homes to me, people I meet online or on the road, friends and friends of friends, all sharing their stories with me, their wisdom, all in their own way supporting my adventure, giving me true blessings.
I already have more stories than I could fit into a fat book.
One last thought: I’m still learning and growing all the time, of course. In fact I feel an acceleration in this regard. This trip, I hope, is not my final draft, not even close. And given that it’s going so well, that I’m having so much fun, just imagine where I might be headed from here.