The Hardest Part of Life on the Road
There’s a moment during every Travel Season where I become completely convinced we’ve made a mistake.
Usually, it happens the first night in a new place.
We’ve been driving for hours. The car is packed awkwardly with leftover groceries, suitcases, backpacks, Lincoln’s things, and a bag of refrigerated medication I’m trying not to forget.
We finally arrive, exhausted.
Then begins the strange process of rebuilding a functioning version of life in a completely unfamiliar space.
Where do shoes go?
Which cabinet makes sense for snacks?
Can we hear the neighbors?
Can they hear us?
Where will we work tomorrow?
Is the Wi-Fi good enough?
Where do we walk Lincoln in the morning?
And why do I feel completely overwhelmed everywhere I look?
Nothing is actually wrong, and yet I suddenly miss home so intensely it feels irrational.
There’s a lot about living on the road that’s easy to talk about, like the fact that your Tuesday evening might end with a hike in the mountains instead of traffic and errands.
But for me, the hardest part of this lifestyle is the constant low-level adaptation.
What It’s Like to Rebuild Your Life Every Few Weeks
Somewhere between every couple of days to every few weeks is a moving day.
We’re changing locations, possibly states, as we move from one destination on our itinerary to the next.
To make this happen, there’s an entire system in place. Work setups are taken down, and monitors are repacked between clothes for safe travel. Lincoln’s crate has to be collapsed first so it can get loaded into the only place it fits in the car. Clothes, suitcases, hiking bags, work equipment, and random gear go next.
At the same time, we’re cleaning up after ourselves and resetting the space to the way we found it. Leftover groceries become a weird puzzle that goes in the car last, and we’re trying to remember to check every outlet on our way out the door.
Then we drive for hours, arrive somewhere unfamiliar, mentally map a new space, test the Wi-Fi because work starts again tomorrow, unpack enough to function, and try not to have an emotional breakdown because the walls feel like they’re closing in and the couch looks like a germ-filled surface you absolutely cannot touch with your bare skin. (At least in my mind.)
The First 24 Hours Are the Hardest
This took me a long time to recognize as a pattern, rather than treating it like an emergency over and over again. But now I know there’s usually a small adjustment window after arriving somewhere new where everything feels off.
During that window, there’s a very large chance I’ll suddenly feel very emotional and very homesick and dramatically announce (often, with tears) that I miss home and never want to travel ever again.
When I told Jon I was writing about the hardest part of living on the road, I said, “For me, I think it’s those first 24 hours. What about you?”
He replied, completely deadpan: “Dealing with you during those first 24 hours.”
Ha. Ha.
At this point, we both know the pattern. The first night in a new place is uncomfortable and overstimulating. Then, within 24 to 48 hours, I’ll shake it off and get back to feeling the magic of this marvelous thing we’re doing, bouncing from one dream destination to the next.
This is also one of the reasons we eventually realized we like staying places for a month at a time whenever possible. After a few weeks somewhere, you stop feeling like a visitor and start feeling like someone who temporarily lives there instead. It’s a completely different experience in the best way.
The Hardest Part for Jon Is Different
When Jon actually shared the hardest part of life on the road for him, I expected him to say balancing work and travel.
Which he did, in part.
Specifically, trying to balance work calls and deadlines with moving days. You see, at first, we kept trying to convince ourselves we could handle moving locations during workdays because neither of us wanted to “waste” a full weekend day packing, driving, unpacking, and resetting life somewhere else.
Surely we could just work an 8-hour+ day AND relocate our entire functioning existence at the same time. Right?
Eventually, we had one particularly terrible move day in the Canadian Rockies that left both of us exhausted and overwhelmed, sitting in a very quiet car after trying to juggle meetings, checkout times, and packing all at once.
That was the day we looked at each other and said, “Okay. Never again.”
And then, naturally, months later, we forgot this decision and did it again anyway. 🙃 Because no one wants to sacrifice a weekend day when there are mountains outside and hikes to do and places to explore. (We regret it every time. Keeping this here as a note to self.)
But then Jon surprised me and said, “The hardest part is eating healthy on the road.”
To be fair, we don’t cook a ton at home either, but on the road, we’re even less likely to cook because it’s not our kitchen, pans, or utensils. Sometimes the whole kitchen setup just feels vaguely gross, and the idea of making an elaborate healthy dinner is unappealing.
It’s also challenging because there are so many temptations on the road. We want to try the local bakery. The breakfast place everyone recommends. The brewery after a long day. The seasonal desserts you can’t get at home. That’s part of why we’re here.
Throw in the lack of structure on the road, and suddenly it’s much easier to justify burgers after a hike, pub fries for dinner, or grabbing donuts “just this once” for the fourth time that week.
So for Jon, the hardest part is balancing it all at once: work, travel, healthy habits, moving constantly, and occasionally his wife’s highly sensitive nervous system. 😉
But for both of us, what’s happening around us—watching the sunrise over the Atlantic during a hike in Acadia, climbing a via ferrata through some of the most immersive mountain scenery in the Canadian Rockies, or drinking the best hot apple cider of your life while wandering around Salem on Halloween night—makes all of it worth it.
I wasn’t kidding about the couch thing… so Lincoln and I both get our own designated spots :)
Who wants to skip dessert when an apple cider donut ice cream sandwich is on the menu while spending fall in New England?
More on Road Trip Locals
🌎 Curious what our Travel Seasons actually look like? Browse our Travel Seasons for real-life itineraries, destinations, and what everyday life looks like while working remotely around the U.S. and Canada.
🧳 Wondering what we pack for months on the road? Check out our complete Road Trip Packing List for the exact gear, work setup, road trip essentials, and random things that make this lifestyle easier.
🐻 In the mood for adventure? Read Alaska Diaries, our seven-part travelogue from the time we roadtripped Alaska for 21 days to visit all 8 national parks.
✉️ Wish your inbox got more postcards and fewer emails? Join Postcards from the Road, our weekly-ish email featuring memorable travel stories, beautiful places, and behind-the-scenes moments from life on the road.
Related Posts
