Reading · Those Who Wander

Read more about it here and enjoy an excerpt from the book here.

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To learn more about the book, please visit here, and you can listen to my latest conversation about the book on a podcast with the New Books Network here and on Spotify:

Years ago, while living in Steamboat Springs, Colorado, I was working on Mount Werner for the ski resort, hauling food and beverages up the mountain on snowcats in the evenings. Hilary and I had recently moved from our home state of Indiana to Colorado and were just getting settled into our cozy one-bedroom apartment. A couple we had met while backpacking the Appalachian Trail a few years before contacted us to see if we’d be willing to host a fellow backpacker they knew who would soon be coming through Steamboat on the Continental Divide Trail (CDT). Of course!

They stayed with us for a couple of days, hanging out in our still barren apartment, enjoying pizza, and telling us all about the CDT—a monumental trail running from Canada to Mexico straddling this colossal geological feature of the Continental Divide of the Americas. This was the first time the CDT entered my mind, and I’ve been dreaming about it ever since.

The following spring, I came very close to venturing out to do the New Mexico portion of the CDT that runs for approximately 700 miles from the Mexican border, crossing the Chihuahua Desert and multiple national forests before entering southwestern Colorado. I had already eagerly booked a shuttle service that would take me to the border. I had all my gear prepared and had purchased a guidebook, New Mexico’s Continental Divide Trail.

However, as I began to research more thoroughly in the weeks leading up to my intended departure, I realized this portion of the CDT required a lot more logistics than the Appalachian Trail, namely navigating across open desert and coordinating water caches across the parched landscape. It dawned on me that I was being premature in my planning, and eventually reality set in and I made the decision to cancel my excursion for the time being. I took a solo road trip across the southwest instead, which turned out to be an enthralling journey in and of itself.

I’ve been thinking about the CDT off and on for almost a decade now. That trail feels like the big fish that got away. In the last few years, I’ve been slowly piecing together a grand adventure in my mind: A dream journey that begins in an Amtrak train terminal in Chicago’s Union Station on July 1, 2039. I am standing in the terminal with nothing but a backpack, my cherished hand-carved hickory walking stick “Wiseman”, and beside me is my 18-year-old son Walden, who will have graduated from high school only a few months before. We are about to depart on Amtrak’s famed Empire Builder route to Glacier National Park, where we will begin our southbound journey to hike from the U.S.-Canada border to the U.S.-Mexico border for half a year or more for 3,100 miles through mountains and desert, eventually making our way back to Santa Fe, and then finding a return train back home.

That is the general model in my mind so far anyway, and I could just leave that happy dream where it is. However, lately I’ve been realizing that if I am serious about doing this one day, I need to be planning now and being more deliberate with my time if I ever want this dream to manifest.

Walden is only five years old right now, and while he’s becoming quite a traveler and hiker already, it will take some convincing and finessing over the years to keep him hooked on the outdoors, especially long-distance backpacking. I plan to try our first backpacking trip this fall on one of Indiana’s “long”-distance trails—the Tecumseh Trail—which runs for 42 miles through nearby state forests and would likely only take us a long weekend to complete. Then it occurs to me, “What if he ends up hating the outdoors and becomes yet another adolescent addicted to the internet and video games, only wanting to while away his teenage years in Mark Zuckerberg’s 15^th version of the Metaverse?” How tragic would that be? I think it’s unlikely…

Our son Walden showing his American spirit and muscles on our recent road trip through Maine. Photo by the author.

Assuming Walden will live up to his namesake and he wants to pursue a simpler and more deliberate life than losing himself in cyberspace, what else do I need to be thinking about? How does one ultimately plan something that is 13 years out anyway? And what if all my dreaming and planning falls apart in the end and it never happens?

Staying in shape and keeping my knees strong will be high on the list of priorities. I know I can maintain an active lifestyle by continuing to do things like training jiu jitsu, running, hiking, and biking as I’ve been doing for many years now.

Savings will also be an obvious priority. Perhaps I can be more frugal and build a separate “grand adventure” fund in the meantime. Accruing enough savings to take a six-month hiatus from work will be challenging, but budgeting over 13 years should make it much easier and less anxiety-ridden. Initiate the Excel spreadsheet!

Keeping up to date with backpacking gear and supplies. There’s plenty of gear and supplies that I could be researching and gathering too in the meantime, and I’ll also want to stay aware of all of the news affecting the CDT (I am already a subscriber to their newsletter).

These three broad objectives seem easy enough to plan around, but what about all the uncertainties I do not have the power to foresee that could completely sideline this grand adventure I’ve imagined? After all, there are far too many contingencies to contend with (so it goes), and I can get derailed by too much “what-if” thinking: what if I get seriously injured or lose my job in the coming years? Maybe my knees are destined to be completely shot by the time I’m 50. How much could all these potential scenarios thwart my dream journey?

And a lot could change between now and then. Will we even want to be separated from the rest of our family for that long? My solo trip to Ireland a couple of years ago made me realize just how challenging it is to be away from home and family for even a short period of time. The thought of being separated from my family for six months or more is already unthinkable…

In the coming years, I know there will be a lot to ponder, but I think maybe the greatest thing to help keep me at ease is, ironically, to accept that maybe this grand adventure won’t happen at all. Perhaps that sounds too defeatist or fatalistic on the surface, but I believe there is something edifying here. I will obviously continue to plan physically and mentally for this grand adventure. Still, we should not underestimate the emotional training that is often neglected in planning our adventures, especially when plans fall apart.

I used to tie myself up in knots when things didn’t work out exactly as I'd planned. I was rigid and hard on myself. Like a child throwing a tantrum because I didn’t get my chocolate bar as a treat, I’d be enraged with myself or blame it on others or often “the system,” some abstract entity that had wrecked my plans. Yet through these many iterations of travel plans going astray, I was forced to accept my folly, temper my reactions, and choose an alternative route of adventure. In time, this painful lesson has sunk in.

I’ve since learned that f***ing up one’s travel plans only invites unexpected adventures. You have to cultivate the right attitude and mindset. That’s part of maturing, I suppose. However, even mature people fail to grasp this lesson. There is a kind of superpower to be learned here: You can pivot when things don’t work out. Like water over stone, you can learn to flow with much more ease around obstacles and train yourself to be better composed and clear-headed in the midst of the unexpected struggle or unplanned roadblock, which is perhaps one of the most edifying lessons of life.

So if I put 13 years into planning a grand adventure and it never comes to fruition, I will end up not having staked everything on it happening. It took me too long to realize that in all my planning for my trips, I never factored in the possibility of something not happening, and that only led to a great deal of mental strife. I’ve already permitted myself to imagine alternatives. Maybe we’ll be doing something else entirely different come July 1, 2039, and that will be okay too, even if it isn’t all that “grand.” Maybe we’ll be on a road trip, or hiking somewhere else, or visiting another country, or perhaps we’ll just be harvesting summer crops in the garden at home just as we were the other day.

Walden helping me construct, cultivate, and harvest our "grand garden." Photos by the author.

I’ve now learned that the earlier we accept that the big fish we were desperate to catch may forever remain out at sea, the sooner we can begin to live a more equanimous life. Once you’ve traveled for a while and been on numerous adventures, you begin to realize that things rarely go according to plan and you must be flexible and adaptable if you want to remain adventurous. I think this is where mindfulness practice and meditation have also helped me considerably: That we can be simultaneously working toward something or improving ourselves and entirely accepting that things may never come to fruition in the end. To accept things exactly as they are or will be, all the while striving to manifest our dreams, is the beautiful paradox of life.

For consideration:

What’s the grand adventure you’ve been dreaming of doing?
How do you think of preparing yourself for it?
How would you feel if you never achieved your dream adventure?

The Grand Adventures Far Down the Road: Preparing for a Dream Journey That May or May Not Happen

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