Lessons of Route 66: On Expectation, Disappointment, and Trusting the Journey

I am scheduled to drive from Boston to New York City next Monday, January 5^th to drop the Blue Car at the shipper’s warehouse near Port Newark.

We had three inches of snow yesterday. And the Blue Car is still in the shop.

I watched the snow come down in fluffy, oversized flakes yesterday morning with less than my usual joyful childlike wonder. If you’ve been following along here, you know I love snow. It’s never a bad time to snow. Except now. There’s road salt to think of and I’ve been playing a kind of winter roulette with the weather. It seems I’m losing. So, yesterday morning after gazing out the window at 5 a.m., I made a cup of tea and climbed back under the covers to ponder the state of things. Will the car be fixed? Will the roads be clear enough to get it to the container port on time?

This has me thinking about something I grappled with during my 2023 road trip.

How do we let disappointment exist without letting it hijack the journey?

In late November of that year, three months into my trip, I finally made it to a section of historic Route 66—the storied American highway that stretches 2,400 miles from Chicago to Santa Monica.

Route 66 is known as The Mother Road. It symbolizes American mobility, freedom, and the pursuit of dreams. When this national highway opened in 1926, it offered the shortest year-round route between the Midwest and the West Coast for the more than 19 million vehicles on the road at the time. It was stitched together from mostly existing dirt and gravel local roads, assembled under federal roadway design and signage standards.

Over time, it became peppered with quirky roadside motels, tourist attractions and gas stations and was a roadway steeped in myth and legend. Towns and cities along the route prospered until Interstate 40 was completed, offering a faster, more efficient alternative that bypassed the fabled road. In 1985, Route 66 was officially decommissioned, no longer serving a purpose of national importance.

Route 66 had loomed large for me since adolescence. I was in awe as my older brother embarked on road trips along parts of the route with his buddies, and I harbored more than a little envy. As an adult, I’ve listened to his stories of countless motorcycle trips along its length.

My architect’s sensibility loves the quirky designs of the roadside diners, motels, and gas stations that once peppered the route—each expressing a distinct sense of place and time. And my movie-loving side holds reels in my head of the mythic proportions this road occupies in our collective American consciousness: Cars, Thelma & Louise, Easy Rider, and so many more.

So, my anticipation was high as I left Joshua Tree, heading north toward Las Vegas for my first encounter with Route 66. The road was lonely and flat, offering stark Mojave Desert views and limited signs of human habitation. I was warned that morning to start the day with a full tank of fuel, plenty of water, and snacks. Cell service would be spotty, and there was no guarantee of finding open gas stations along the way.

When I arrived in Amboy, I saw the iconic Roy’s Motel and Café and took full advantage of the photo opportunity. The Blue Car looked as cool as ever against the towering sign and dramatic sky.

I left Amboy and Roy’s expecting more iconic destinations ahead. Little did I know the peak moment of the route was behind me. I faced mile after mile of eerie, desolate road. I was disappointed but told myself there would be more to see later in the trip.

After visiting national parks in Utah and spending Thanksgiving at the Grand Canyon, I found Route 66 again in Arizona. I drove through Winslow, then later through Gallup, New Mexico and on into Texas. For most of my time on this most famous of American roads, I encountered discontinuity and absence.

This roadway, which has occupied so much of our cultural imagination, is now a shadow of its former self. I had a hard time focusing on what remained and felt despair for what was gone. 

I could appreciate the isolated spots that celebrated the past, but the vast amount that was missing left me feeling empty inside. When I finally left Route 66 and returned to I-40 in Texas, I came to terms with a reality far different from the myth. My search for the Route 66 of my dreams—the Route 66 of American consciousness—taught me the perils of high expectations. Try as I might, I couldn’t shift my focus from the lost places.

A few days later, I arrived in Hot Springs, Arkansas, to a mostly deserted summer resort town and a long-past-its-prime grand dame hotel, cold and rain-soaked. It felt like an echo of my Mother Road experience. I sensed ghosts in the hallways of that big, dilapidated hotel as I felt the winding down of my trip.

I still had some stellar destinations ahead—Memphis, Nashville, Asheville, Washington, D.C.—but the rhythm was slowing, and so was I. One hundred five days on the road is a lot of days, and I could see my limits. I felt grateful that my internal traveler odometer somehow matched the number of miles separating me from home.

My experience on Route 66 was my first real disappointment of the trip. And that disappointment taught me something I didn’t understand then—but I understand now, staring at the snow and waiting for the Blue Car.

On that storied American road, I found disappointment without crisis. The stakes were low. I hadn’t built my entire road trip around Route 66; it was only a few days out of 105.

Now, with uncertainty around the Blue Car’s repairs and worries about road salt, the emotional stakes feel higher—and the lesson more critical to hold close.

I can’t control everything. I can’t even control most things on any given day. But I can control how I respond to disappointment and unmet expectations. I can acknowledge disappointment without scrambling to fix what I can’t. I can accept uncertainty without letting it unmoor me or drain the excitement from my life.

Yesterday, I looked out the window and felt suddenly and surprisingly unsettled. I have very little certainty about how the start of this upcoming trip will unfold. On my last road trip, I packed the car the night before, woke at dawn, and drove. The early roads through Massachusetts were familiar, and my first destination was close to home. Any uncertainty I felt then—if I felt it at all—was about the weather or how hot it might get, and perhaps whether the Blue Car would make it through the entire trip with flying colors. It did.

This time, the uncertainty isn’t abstract. It’s real. And much of the start of this trip lies outside my control. I must muster my trust and believe in my judgment: in an excellent mechanic and a good parts supply chain, in a smart shipper who will understand the Blue Car’s quirks and how to start it after weeks in a container crossing the Atlantic, and in the whims of weather and the skills of the ship’s crew tasked with delivering the car safely to Le Havre.

Some of these uncertainties have existed for a while. But the snow yesterday—and the Blue Car’s presence not in the garage behind my building, but in a mechanic’s shop—piled it all on. Enough to send me briefly back under the covers instead of rushing out to don my coat and mittens and play in the snow with Leo.

I’m trying to remember that, just like my days on Route 66, if my expectations aren’t met, I need to allow disappointment to exist without fixing it. I need to allow the circumstances themselves to be the trip—to be the experience—without believing they are hijacking the adventure.

Yesterday, I told a close friend that I don’t have the Blue Car back yet. He asked, “What are you going to do?”

Watching the snow fall and thinking about the eight days ahead of me until I need to be in Port Newark, I considered the possibility that I may need to acknowledge disappointment and simply drive on. What will that mean? The car may leave later than scheduled. I may need to flatbed the Blue Car to the port to avoid salted roads. I may change my plane ticket to a later date. I could spend more time in Europe before the Blue Car arrives. There may be even more drastic changes to my plans.

While I know the start of this trip may not happen the way I envisioned, it seems pointless to spend emotional energy on hypotheticals. Just like my time on Route 66, I intend to keep driving in one way or another—even if the road fails to deliver what I imagine and hope for before the trip even begins.

With this in mind, I eventually went outside into the winter wonderland and took Leo to the dog park. I ran some last-minute errands, finished most of my packing, and got everything ready to stow under the front hood of the Blue Car when it returns.

And unlike my time on Route 66, I am focused on what is here and possible.

What is present. Rather than what is missing—or what might not be.