What It’s Like Traveling and Working Full-Time as a Couple

life on the road

Aug 12

Written By Kelly W

One of the best parts of traveling together for months at a time is how extraordinary places become the backdrop for everyday life. We’ve taken work meetings inside national parks, shopped for groceries in small mountain towns, walked waterfront parks while our clothes spun at a nearby laundromat, and given each other the silent treatment while driving through the Rockies after a long moving day.

Traveling together doesn’t mean we’re on vacation together for weeks and months. We’re still working full-time, figuring out dinner each night, taking care of life responsibilities, and (occasionally) getting on each other’s nerves. We’re just doing it all while moving from place to place around the U.S. and Canada.

Here’s what it’s like for us traveling as a couple full-time, while working full-time, too. This post is part of our Living on the Road series. Keep reading:

👋 Meet Us: We’re Jonathan and Kelly, and for five years, we lived on the road for weeks and months at a time—working full-time, building routines in new places, and turning everyday life into a series of road trips. We’ve spent our “Travel Seasons” exploring everywhere from the Canadian Rockies and Alaska’s highways to New England in the fall, and along the way, we’ve learned how to make life on the road feel normal, sustainable, and really, really fun.

We’re Together a Lot

Like… a lot. Moving days, workdays, errands, road trips, travel days, meals, hikes… You name it, we’re doing it together during Travel Season.

That’s actually one of my favorite things about this lifestyle.

We get to experience everything together and make tons of memories. Like returning to the same restaurant in New Hampshire for the fourth time during a month-long stay because we can’t get enough of the buffalo chicken tenders. Or getting up early for trail runs with Lincoln during the weekdays in Vermont because it’s the perfect fall workout.

Whether we’re rushing to a sunset hike after work or having long road trip conversations after packing up one stay and heading to the next, we don’t have to wait for weekends or vacations to spend quality time together. On the road, it’s built into everything we do, and that’s something I don’t take for granted.

We Usually Work Side-by-Side

At the same time, traveling and working together full-time means sharing physical space almost all day long. Most of the time, we actually work from the same kitchen table.

Jon works a traditional corporate job. From Monday through Friday, morning to evening, his days are meeting-heavy and fairly structured. He needs a reliable setup, a quiet environment, good Wi-Fi, and enough table space for a second monitor.

I’m a writer, so my work looks completely different. Most of my day is long stretches of focused writing, usually with headphones on so I’m not distracted by the calls Jon has to take. As long as I don’t have a client call at the same time he does, we work together pretty well.

We’ve spent entire months working side-by-side at kitchen tables, breakfast bars, countertops, desks, and coffee tables. Even though we don’t need separate spaces, the layout of a place still matters. When we’re choosing somewhere to stay for a few weeks or a month, we pay attention to whether there are at least two places where we could work.

That’s because if we both need to be on a call at the same time, then one of us needs somewhere else to go. A second bedroom is ideal, but it doesn’t have to be that formal. An outdoor patio with a table can work. So can a desk in another room, a kitchen counter with a stool, or even a second small table somewhere else in the house. The specific setup matters less than having options.

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We Divide and Conquer

I’m not sure if we consciously talked about this, or if it just happened naturally over time. But we have specific roles during Travel Seasons.

For example, Jon drives, and I pack the car.

Before a Travel Season starts, I do most of the research. I’ll map our route, find places to stay, look up hikes to do, and build the overall flow of the trip. Then, I’ll take what I’ve found and various options to Jon so we can finalize our trip together.

Once we’re actually on a Travel Season, Jon handles more of the in-the-moment logistics. He’s getting us from place to place, making reservations, keeping us on budget, and just generally leading the way.

When it comes to traveling with our dog, Lincoln, we have roles there, too. Jon takes Lincoln out at night, while I walk her in the mornings. Sometimes we’ll join one another, especially if we’re turning the morning walk into a trail run so we can get some exercise in, but if Jon has an early morning meeting, we already know I’m on walk duty.

I’m also the one who usually packs up Lincoln’s things on a moving day, while Jon is the one who’s going to clean the dishes, run the dishwasher, and tidy the kitchen. I’ve taken apart Lincoln’s crate enough that it’s second nature for me, and he’s bothered less than I am by a mess in the kitchen.

None of this is rigid, but after years of traveling extensively, we’ve naturally figured out what makes moving days easier and what causes unnecessary stress during a season. Having roles makes it easier to pack up and move between locations, but it also reduces some of the mental load on the road.

Each of us is only in charge of some things, not everything.

We’ve Learned Each Other’s Patterns

This is one of the biggest keys to our success on the road as a couple. When you spend this much time together, you get pretty good at recognizing what the other person needs.

For example, I struggle the first 24 hours in a new place. When we arrive somewhere new, especially after a long travel day, there’s usually a small window where I’m overwhelmed and overstimulated. I’m trying to mentally map the space, unpack our things, settle Lincoln, decide where everything goes, and regulate all of the “everything is new” feelings happening at once.

During that period, there’s a decent chance I’ll tell Jon we’ve made a terrible mistake and we should never travel ever again. Jon, to his credit, has learned not to take the bait. He gives me a lot of grace during that adjustment period and reminds me it’s temporary. Usually within a day, I’m back to normal and talking about how magical Travel Seasons are again.

The same applies in the other direction.

Jon has a demanding full-time job. There are days when work has to take priority. Sometimes that means he needs to stay in and catch up on work instead of exploring. Sometimes it means he needs me to handle more of the packing or logistics because he’s trying to finish something before we leave.

We still remember (and now laugh about) one particularly chaotic moving day in the Canadian Rockies. We were leaving Calgary and heading toward Lake Louise. Jon had one last meeting he had to take before we could leave, so I was packing the car by myself, cleaning up, and checking out, all while trying not to make too much noise or be visible in the background of his video call. It wasn’t ideal, but it was the tradeoff we chose to make in the moment.

When we’re traveling and working full-time, we do our best to give each other grace and think in terms of the team. Who has more capacity right now? And what would make this easier for both of us?

We Make Decisions Before We’re Tired

Decision fatigue is very real when you’re living on the road.

If every day is a constant stream of questions like… What do you want to do today? What do you want to eat today? Where do we want to go today?

Then at some point, you’re both going to get tired. And if you’re anything like us, when you’re tired, you’re more likely to lash out.

So instead of deciding everything in the moment, we make a surprising number of decisions ahead of time.

We know what our biggest priorities are for a place before we even arrive. We know what hikes matter most to us, what restaurants we’re excited to try, what days are going to be bigger exploration days, and what days need to stay slow because work is busy.

Mondays and Wednesdays naturally became chill nights for us over time. Those are our “normal life” evenings where we grocery shop, catch up on work, do laundry, stay in, or just rest.

On the other days, rather than constantly negotiating plans after a full workday, we’ve already booked tickets, picked hikes, and made dinner reservations… so in the moment, we can just follow our plans and enjoy.

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We Say What We Need

Or at least, we try to. Because there’s not much room for passive aggressiveness when you’re sharing a one-bedroom Airbnb, working full-time beside each other, and spending ten hours together in the car the next day.

Over time, we’ve gotten much better at just saying what we need.

“I don’t want to make another decision today.”
“I need to catch up on work.”
“I need a movie night with nothing to do.”
“I need to get outside.”
“I need you to handle this part of today because my brain is done.”

We’ve also learned how to give each other space, even in small ways.

Sometimes that means one person putting on headphones and disappearing into work for a while. Sometimes it means one person going on a coffee run alone. Sometimes it means working from a different room for the afternoon. Sometimes it just means recognizing that the other person is tired and not taking it personally.

We love traveling and working full-time together, but that doesn’t mean this lifestyle is perfect all of the time. There are tradeoffs.

Some days are incredible, while other days are stressful. Some days everything flows, while other days the Airbnb feels too cramped, balancing travel and work is overwhelming, and you’re not sure how much longer you can do it. That’s normal too.

For us, long-term travel got easier when we stopped expecting every moment to feel magical (even though a lot of them will!) and started treating it more like real life happening in magical places.

We’ve had some of our best conversations on the road… while driving through backcountry Wyoming, going on post-work walks with Lincoln in the Smoky Mountains, and sitting by the firepit in Ellsworth, Maine, during the middle of October.

There’s something about constantly stepping outside our normal routine that makes us reflect on our lives more consistently, and it’s one of the best parts of traveling together as a couple. We’ve got the time (and the stimulus) to connect more deeply, more often.

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