Valid location required
Valid location required
Valid location required

How I avoided letting loneliness get the best of me during a yearlong solo road trip

Some important lessons learned during a cross-country trip in search of a new city to call home

In the summer of 2017, a breakup left me with nowhere to live. But the idea of apartment-hunting in New York—my home state where I had lived my entire life, even for college—didn’t feel right. I wanted to see what it was like to make another place my home. The problem? Because I had never lived outside of New York, I didn’t feel confident committing to a year-long lease in a city I didn’t know.

Fortunately, the breakup also coincided with me starting a completely remote job. I wondered: What if I drove across the country and back to “audition” six cities for one to two months each, long enough to get a real understanding of what it was like to live there? After setting off in October 2017, I lived in Boston, Massachusetts; Asheville, North Carolina; Austin, Texas; Denver, Colorado; Chicago, Illinois; and Portland, Oregon. I returned to New York a little over a year later.

Pacific Coast Highway, California. | Photo courtesy of Dana Hamilton

I will never forget the shocking beauty of driving up the Pacific Coast Highway from Los Angeles to Portland, or passing ranches at sunset as I traveled the entire length of Texas from Austin to Denver, or the giant rock formations of the scorching deserts of New Mexico and Arizona.

There were challenges of being on the road, of course; the tediousness of unpacking and repacking my car at every overnight stop, the annoyance of living out of a suitcase, and the nausea that would stir up at the mere thought of eating another McDonald’s french fry. Road trip food is fun at first, but eventually you get sick of eating like a twelve-year-old at a birthday party.

But perhaps more than anything else, I’ll remember the crippling loneliness I never expected to feel.

My first stop in Boston was a dream. I felt liberated, excited, and happy. But that leg of the trip only lasted two months and I was riding the high of starting my adventure. By the time I made it to Asheville, the reality of being away from my friends and family for the better part of a year set in.


My time in North Carolina in the dead of winter was the loneliest leg of my journey, but I felt stretches of loneliness in Austin, too. I almost quit the trip halfway through. That is, until a friend I met on the road gave me a new mantra: “You’re a maniac and you can do this.” I repeated that to myself more times than I can count.

After getting over the hump of Austin, things picked up. By the time I got to Denver, I had mastered coping with being away and the trip finally started to feel second-nature, like I had been doing this all my life. In fact, after the year passed, the idea of staying in one place—all I had wanted during the lowest parts of my trip—didn’t sound so appealing anymore. I decided to spend another year on the road in 2019.

It took a lot of missteps to get to a place of not feeling lonely while traveling alone, and I want to pass along my biggest (and hardest-learned) lessons.

Getting enough sleep was crucial

Each time I rolled into a new place, I had a hard time relaxing. Yes, I wanted to explore and do everything right away, and was barely able to sleep. But also, the body knows when you’re in an unfamiliar place. It knows it’s not in its usual bed, walking streets not familiar to it, and isolated from other comforts like people and things it’s used to. And because of that, tension I had no control over set in. My body was on high alert, trying to make sense of its new surroundings. And those surroundings changed every few months. It took a toll. I quickly realized that if I wasn’t careful, I’d overexert myself way too fast.

Something I wish I knew before I started this trip was: Driving takes a lot out of you, both physically and mentally. I had to deal with everything from an aching pelvis to cramps in my calves from pointing and flexing my foot on the gas pedal. My neck and shoulders got sore. (I’d ultimately start taking CBD oil as soon as I buckled my seatbelt to help alleviate the tension.) I also realized the hard way that my daily driving cap was seven hours. I had ignorantly scheduled in a few eight-hour drives before even hitting the road, thinking, “I can handle that. How hard could it be?” Very hard, as it turns out.

Somewhere in Portland. | Photo courtesy of Dana Hamilton

Through trial and error I learned to always book an Airbnb with a private bathroom and a tub. Soaking in a hot bath full of Epsom salt after a seven-hour drive helped ease sore muscles, and prevented my body from completely falling apart.

The mind is a different matter. After a long drive, I would find myself wired and having a hard time falling asleep. My mind was filled with visions of double yellow lines and traffic flashing by. But sleep is important, and rather than getting burned out from exhaustion, I learned to prioritize getting enough sleep. Without it, the feelings of loneliness would only get worse.

Too much screen time made things worse

One of the blessings of being on the road is the ability to stay in touch with friends and family via text, email, social media, and Facetime. Chatting with the people close to me seems like a great cure for loneliness, right? Wrong. Constantly being on my phone made me feel worse. Many studies have shown the negative effect screen time has on mental health—and I was no exception.

I found limiting my screen time didn’t mean limiting my contact—I just had to limit my contact over those specific mediums. While I stayed in 33 Airbnbs over the course of the last year, I ended up sharing my addresses and itinerary with loved ones, so my friends and family could mail me things along the way.

Receiving things like cupcakes from a coworker while celebrating my 30th birthday in Austin, a package full of LUSH products from one of my closest friends while living in Chicago, and a card from my mom while I was living in Boston seriously made all the difference. Plus, writing letters felt like a diary entry and helped me get all the icky lonely feelings out (and receiving mail certainly feels more special than a text). Postcards are also great because the ones I received on the trip were memorable souvenirs once it was over.

Networks are made to be utilized

In cities where I didn’t know anyone, I would enjoy the anonymity for a bit—but after a while I started to crave real, human contact. I learned the easiest way to get it was to put a call out on social media. It was as simple as posting “Does anyone in Missoula want to meet for a coffee?” on my Instagram story. I ended up making four new good friends on this trip because they followed me on social media and reached out. I also asked around my pre-trip friend group—because sometimes a current buddy had a cool cousin in Omaha or a former mentor in Spokane. I met some of my favorite people on my trip through second- or third-party connections I didn’t know I had within my social circle.

Pacific Coast Highway, California. | Photo courtesy of Dana Hamilton

People I met on the road were gifts

When I first started the trip, I avoided making connections because I knew they were only temporary. I met a few friends using Bumble BFF (surprisingly not as lame as it sounds) and Tinder (sometimes a date turned into a mutual “let’s be friends” situation), and after a while I stopped trying to avoid making a connection with someone because I was ultimately leaving their zip code.

On the romantic front, it was easy to say “why bother” after a first date with someone I really liked when I only had three more weeks in their city. But one of the best things that happened to me on this trip was someone I dated in Denver saying, “You’re only here for three more weeks? Well, that means we better try to see each other as much as possible before then.” And you know what? I’m glad I didn’t succumb to pessimistic thinking, because the time I spent with his person made my Denver leg of the trip even more special.

I’ll admit it was hard to leave romantic partners, but, in the end, I viewed the time I got to spend with people I dated on the road as a gift. I knew I’d be infinitely happier spending the time I did have with people in six different cities (even after wiping away post-goodbye tears) than if I’d never met them at all. And even now, post-road trip, I still keep in touch with a few people I used to date. I also learned to embrace not knowing what the future holds and accept that some may reappear in my life later down the (figurative and maybe even literal) road.

Remember that it takes time

In the beginning, there was a lot of pressure on this trip to be amazing. So when it started getting hard, I was thrown off. I was living everyone’s dream, right? So why was it so hard? I then realized I couldn’t expect to become an expert overnight at being away from my friends and family. My trip only started becoming “easy” eight months into it.


I made a comparison that made me feel infinitely better: Was my first day of college fun, comfortable, and amazing? Nah. It was terrifying and awkward and sad. College was infinitely easier and more fun the second semester, because by then I knew how to navigate the campus, had a new group of friends, and learned how to handle my course load. A road trip, just like college, is a huge adjustment. Once I cut myself some major slack and gave myself permission to adjust (and convince myself that taking the eight months it took me to do it wasn’t me being a “failure”), the pressure to be “perfect” at navigating this huge life change and for everything to be “amazing” finally lifted.

Loneliness, like everything in life, is temporary

Sometimes it felt like the trip would never be over, that I hadn’t seen a loved one in forever and that I wouldn’t be able to wait until I could see them again. But I endured. I knew my trip would eventually have an end date, and my friends and family were waiting back home for me, thrilled by the idea of our eventual reunion.

During my most trying moments, I reminded myself that I was fully in control of the trip. I decided when it started and I could always decide to stop it—there was no shame in taking some time to return home to refresh between cities or end the trip early entirely. Though I never did it, giving myself the option to do it if I needed to was tremendously helpful. Even if it meant pulling together money for a plane ticket or figuring out a place to leave my car while I headed back to New York for a stretch, there was always a way to figure it out and there were no rules. I would never be a failure for restructuring my trip. Letting the fear of not being viewed as “strong” or “independent” would have held me back from doing what was best for me.

A nonconventional lifestyle comes at a cost

I gave up certain luxuries—a bed to call my own, home-cooked meals, and, yes, easy access to friends and family—in exchange for a beautiful adventure I’ll always remember. A road trip is an opportunity many do not get to experience. While the loneliness is temporary, the memories are not.