Sometimes, when I’m driving a new highway across a new landscape, I think, “Shouldn’t I be more excited about this?” Is it the lack of caffeine? I’m just not that thrilled.
At other times, it hits me—you’re doing it, you’re doing what you’ve wanted to do for 20 years—and tears of joy fill my eyes. There are distinct moments when this happens, and they cut like a razor into my memory. These memories are sharp, crisp: The pelican soaring over me on the miles-long bridge across Oregon Inlet, as I belted out “Man in the Mirror” and felt as free and liberated as that bird. The opening of New Mexico, God’s country, where the subdued palette and brown, pointy mountains held my mouth agape as I drove across Route 380, through the Valley of Fires.
But more often, I’ll have these moments on the road where I think, “Didn’t I feel a lot more excited the last time I drove across the country?” Granted, I was seeing everything for the first time. Over a decade ago, I was on a three-week vacation, and also fueled by strong coffee every morning, which I’ve since traded for tea. These travels feel distinctly different, maybe because they’re not a vacation. It’s not a three-week road trip after which I return to my 9-5 job. I’m living on the road. It’s the feeling of days unfolding without any real structure. I’m just out here. Wandering.
I keep coming back to the same question: What am I going to do “afterwards”? Will there BE an afterwards? This is not a college gap year. This is not time away after the kids have left home. This is not retirement. Will this life simply go on, or will I return to a 9-5 and join the masses again, settle, rent a place somewhere, go “back.”
This question is in the back of my mind at all times. Not necessarily burning a hole in it but certainly penetrating through my every day. I wanted to see if freelancing was sustainable because everyone said it’s not—multiple people who’d tried it for a few months up to a few years before giving up. Extremely talented writers and editors. They all gave up. I’ve already learned that you have to do twice the work for half the pay. Journalists already don’t make a lot of money and do a ton of work, so this is pretty depressing and not exactly appealing, and yet every day, I am grateful to have the freedom and flexibility of being a freelancer, and I’ve been determined to make it work. After being laid off, I spent eight months in Baltimore “making it work” until my lease was up in May. That showed me that freelancing is possible. The road less traveled, but possible if you really wanted it.
The next question: is freelancing while living on the road sustainable? I am obviously still figuring out this next level of the experiment. So far, it’s working, but it’s a logistical nightmare. Even Kerouac had a home base with his aunt, somewhere to retreat to and do his writing before leaving again to hit the road. After a week or so of traveling and staying with friends and friends of friends, I get the overwhelming feeling that I need to hole myself up in a room in front of my laptop and write for 12 hours straight. Then repeat. The writer in me is ready to burst. I totally understand how Kerouac poured out “On the Road” in a matter of weeks.
On my second-to-last onsite writing assignment in Baltimore, I took an Uber across the city to get back to my parked car, and it seemed fateful. The driver wasn’t particularly chatty, but after a few minutes, I found myself asking questions (all these years of interviewing people is hard to shake). He said he’d been driving all night and into the morning, was a registered Uber driver in multiple states in the region, and made a life of it. He brought in enough money each month to live in hotels. To live, in a word, nomadically. I was intrigued. For every other Uber driver I’d ridden with, the gig was a side hustle, just to bring in some extra cash, to supplement. This guy went through a nasty divorce a year ago and said fuck it. And LIVED “fuck it.” Sold everything he owned. Began his life on the road, quite literally. “I’ve never been happier,” he said, as he dropped me off. We wished each other luck in our nomadic lives. I guess it’s just in some of us.
I keep wondering if this whole experiment is just a youthful notion, a pipe dream realized for a short time before it gives way to the standard American life. Doesn’t every teenager dream of traveling the country? Do they just grow out of it, replacing those thoughts with dreams of getting married, buying a home, and having kids? Do I still carry that deep desire because I don’t want kids? Is this something I have to get out of my system, or is this who I am? A nomad. A writer. Someone who simply won’t ever feel fulfilled living the status quo life. I want to find out if another way of life is possible. That’s why I’m here. Yes, there is certainly a spiritual element, and reconnecting with old friends is a bonus, but at its roots is that burning desire and question, to find out firsthand whether a nomadic existence is sustainable or whether it remains a pipe dream for most people for good reason. Figuring it out is worth the risk. So here I am. Figuring it out.