12 Things to Know for Working From The Road
Working from the road, also known as digital nomading, has become increasingly popular in recent years. With the rise of remote work opportunities and technology that allows us to work from anywhere, it’s a great time to take advantage of the freedom to hit the road and work from your laptop, whether you have a corporate job or are self-employed.
Jonathan and I have been working from the road while traveling since 2019.
We spent almost all of 2020 on the road, worked full-time during a 3.5-month road trip in 2021, and most recently, spent 5 months working from the road in New England and Ontario. While writing this, we’re in the middle of a month-long stay working and exploring the Canadian Rockies.
Whether you're a freelancer, an entrepreneur, or an employee working remotely or on a hybrid schedule, here are 12 things to know for working from the road.
Table of Contents Show
1. Use your vacation days (wisely).
When working from the road, it’s tempting not to use your vacation days. After all, it’s somewhat normalized to forgo vacation in a traditional office setting, let alone when you have weekends and evenings to explore. (Before we started working on the road, we went over two years without taking a single week-long vacation, and we’re sure we’re not alone in this!)
Since you have weekends and evenings to sightsee, you might not be thinking about when or how to best use any vacation days you have. But don’t skip this! Time off can be a great way to see more and spend less.
Here’s how we think about using vacation days while working from the road.
Generally, the longer we’re in an area, the less time we take off. The shorter our stay, or the more popular destination we’re visiting, the more likely we are to take time off.
If we’re staying in one location for three or more weeks, we generally won’t take time off unless we have friends or family joining us.
If we’re staying somewhere for two weeks or shorter, we’ll consider one or two days off.
If we’re visiting somewhere for just a weekend, we almost always take at least one day off.
We generally prefer month-long stays when working from the road, so if we’re visiting somewhere for just a weekend, it’s likely because that destination is popular and longer-term lodging prices are outside our budget. For these places, we’ll book only a few days and utilize vacation days to maximize our time (and, in turn, minimize our costs). We’ll stay longer in areas where we can get better deals on lodging and generally won’t take time off during those extended stays.
So before you hit the road, we recommend planning ahead with vacation days based on (1) where you’re headed and for how long, (2) how much time you’ll have on evenings and weekends to explore (remember: traveling in the summer means more daylight to explore after work), (3) how much you want to see in an area, and (4) how much you’re spending on lodging.
Depending on how long you’re in an area and how popular that area is, plan ahead by requesting any additional time off you may need. (Time off can also help minimize costs by making it easier to camp in various places without having to worry about an office setup or internet access.)
2. You can still be successful working from the road.
It’s absolutely possible to work remotely while traveling. It’s also possible to be successful on the road in terms of productivity and promotion.
As a self-employed copywriter, I’ve been working from home since 2015. (My job prior allowed three days of work from home, so I’ve been at least hybrid remote since 2013.) Working with other small business owners in similar fields, it’s very common to work from the road, and some people even consider location independence as a marker of success.
However, Jonathan works in a corporate job. In 2019, when I first floated the idea for him to apply for a remote role, he was hesitant. He wasn’t sure how he’d like working from home, and he definitely didn’t think it would help his career trajectory. (Remote work was not as popular or common as it has become since 2020.)
His concern was that remote work would hinder his opportunity to connect with team members, which would, at worst, hinder his opportunities for promotion and, at best, be a neutral change. (In other words, he expected a remote role to close doors, not open them.)
The opposite turned out to be true. Jonathan got promoted within months of accepting a remote position, and he’s now a big proponent of working from the road, often acknowledging how much more productive he is outside of the office. Sure, he misses in-person connection sometimes, but the pros have far outweighed the cons.
It takes discipline, which for us looks like a consistent routine, but it’s more than possible to be successful working from the road and continue advancing your career, whether you’re self-employed or a corporate employee!
3. Your on-the-road office probably won’t be as comfortable.
Before you book somewhere to stay, consider where you anticipate working.
You can plan to walk to a coffee shop, library, or coworking space, or you can work from your hotel (which may also have a business center) or short-term rental.
We’ve spent the majority of our almost four years on the road working from our hotel or short-term rental. We make sure to find lodging that has at least one designated desk area. (Ideally, an actual desk, but a medium to large kitchen table can work as well. Because I travel with a portable standing desk, I’m also okay working from a kitchen island/countertop.)
As you browse lodging, keep in mind where you could work comfortably and efficiently.
Then, once you arrive, set up your workstation and, ideally, keep it up for the entire stay. This way, you have a stable place to work and can more easily bounce between your to-do list and the exploration you want to do in an area.
This said, even when you plan in advance and set up a workstation right away, it’s probably not going to be your best setup ever. Unless you’re traveling in a large RV where you can have a more traditional office, you’ll probably be making some trade-offs when it comes to your desk on the road.
You may not love the chair you’re using, or maybe you have to angle the camera in a strange way to provide a neutral background for Zoom calls, or maybe you have a much smaller workspace than you’re used to. There are many things that may not be as comfortable about working from the road, but the views and activities more than make up for it!
4. You’ll naturally become more flexible and adaptable.
Spontaneity lovers rejoice! You will naturally become more go-with-the-flow and adaptable when working from the road. Because, well, you have to.
Sometimes, you’ll have a poor internet connection. Sometimes, the internet will go down without warning, or a space won’t have the exact setup you expected. You might not have cell coverage when you thought you would.
Working from the road requires flexibility and adaptability, but it does help to have a backup plan.
Invest in Starlink or use your phone’s hot spot if you’re in an area with good coverage. Know where local coworking spots, coffee shops, or libraries are nearby.
RTL Tip: Internet can be tricky for working from the road as you usually won’t know the exact situation until you arrive. Reading reviews has been the best way for us to get a good feel for how reliable the internet is at a hotel or short-term rental we’re considering. Search for keywords like “wifi” or “internet” or “work” to filter for relevant reviews. If you want to be cautious, you can always message the host or hotel ahead of time to confirm internet speed.
It’s great to stretch your adaptability muscle by working from the road, but it’s also helpful to always have a backup plan for important deadlines and meetings.
5. Your priorities may shift. It’s usually great. Sometimes it’s not.
When deciding to travel for half of the year, we Jonathan put together a budget for us to afford months of travel on top of our home base in Dallas.
Among other things, that plan looked like buying below budget in Dallas, reducing our budget for most non-travel-related items, and bringing PB&J back into our regular food rotation.
Since our priority is being able to travel, that’s where we spend a lot of our time and money. Instead of clothes, accessories, or new cars or electronics, we’re generally only investing in travel, with things like hiking boots, travel gear, and car camping accessories.
This is not a problem, as most of our time on the road is spent in the woods, at cideries, or exploring small mountain towns. But sometimes, particularly when we’re meeting up with friends or going out someplace nice, it’s frustrating to have a closet better geared toward a trail than a night out.
This is a small tradeoff for working on the road, but your priorities may shift as you do, and while mostly that’s great, it’s still a tradeoff.
6. People may not fully understand what you're doing.
Working from the road was less common when we started in 2019, but even now, people may not get what you’re doing, fully understand it, or even be extremely curious about it.
Being self-employed, it’s more common for those I interact with, as many digital business owners desire location independence and live non-traditional lifestyles.
However, Jonathan has been working in a corporate role since we first hit the road in 2019. He gets asked a lot of questions about where he is, what he’s doing, and how he does it.
Some coworkers like to play “Where in the world is Jonathan this week?”, a nod to “Where in the world is Carmen Sandiego?”. He often hears his coworkers say they wish they could do this too or ask how he’s been able to.
Even with the more common hybrid schedules and workplace flexibility, taking advantage of that flexibility to travel and explore new places is less common than we expected. As a result, people are naturally curious or may not fully understand it.
7. Being a “weekend warrior” can be exhausting.
Outside of any vacation days or time off planned during your trip, prepare to get in the “weekend warrior” mindset.
Working from the road is about seeing new places and having new experiences, so don't let work overshadow the fun and know going into it that you’ll feel pretty full balancing a full-time job with what can feel like full-time travel.
It’s also helpful to know that you’ll probably get more and more tired the longer you stay on the road working, but it’s SO rewarding. Working from the road can make you feel like you’re living in these different places, not just exploring them. And that’s so memorable! Some of our best travel memories are from morning walks in local parks, testing out new trail runs before work, or the same restaurant we keep returning to because we enjoyed it so much.
Yes, you’re going to try to cram a lot of sightseeing into your evenings and weekends, but that’s because there’s a lot you want to do. So, the fullness is good even if sometimes it feels overwhelming.
The longer you’re working from the road, the more we suggest you plan rest days… days to sit on the couch and watch Netflix or just rest with a leisurely day around town. You will likely get tired as you work from the road, but that’s kind of the point. You’re working and traveling full-time, so give yourself some grace and soak it up as best you can!
8. You don’t have to explore EVERY night.
That said, it really is okay to spend a night catching up on work. It’s okay to watch movies from the end of your workday until you fall asleep. It’s okay to go back to the same restaurant you love for the third time on your trip.
You’ll probably feel a strong pull to explore as much as you can while you’re traveling, and that’s normal. You’re in new places… often places you’ve dreamt of exploring for a while. And there’s probably a LOT to do nearby. This is great. This is why you’re here. But that doesn’t mean you have to explore every free moment you have.
We implemented planned rest days during our third year of working from the road. On Mondays and Wednesdays, we don’t go anywhere or do anything. And we decided this in advance to reduce at least one of the many decisions we make working from the road. Off days are needed when you’re balancing what can feel like full-time work and travel.
But knowing this doesn’t always make it easy to take the rest days. Whether because of FOMO, all you want to see and do, or because you can’t shake the thought that you’re paying a lot to be here, so a night in feels like a waste… You may need a night off but not want to take one.
However, if you’re planning to work from the road for an extended period of time, or this is something you’re hoping to do year after year, then sustainability is the name of the game. (And the truth is… It’s likely more financially and otherwise reasonable to take a night off in a location than it would be to fly somewhere and then back home every weekend!)
Our best recommendation is to think of working from the road as though you’re living in these various locations, not just traveling through them. Since you’re living here, you need to find a routine you can stick with and enjoy. This has actually become one of my favorite things about travel… I love finding favorite trails, restaurants, and hobbies to enjoy while in new areas!
9. The time before and after work is your friend.
Weekends are great to explore but also the busiest days to travel. So, consider using the time before and after work. (On your non-rest days, of course!)
We have room to improve here, but some great memories from the last few years of working from the road come from getting up before work to explore.
While spending three weeks in Ellsworth, Maine, we woke up before work to sunrise hike the Gorham Mountain Loop. While spending two weeks in both Vermont and New York, we woke up three days a week to trail run before work. During a month in Hamilton, Canada, we got up almost every day to walk a nearby waterfront park and then pick up coffee and breakfast at Tim Hortons.
You’re probably already thinking about how to utilize your time after work and on weekends, but early morning weekdays can be great to see places, beat crowds, and start your day in a memorable way!
Thursday morning sunrise hike in Acadia National Park, ME
10. There’s a balance between planning ahead and living in the moment.
Both are great.
Planning ahead is especially important if you’re visiting places with a high volume of tourists. (Think: National parks, auto roads, places with reservation requirements.)
But one of the best things about working from the road is also having time for living in the moment and leaning into the “local” side of travel.
Our recommendation is to plan ahead around the must-do things while you’re in town (particularly the things that require tickets or reservations), but then leave space for each place to inspire you once you’re there, too! Ask locals what they love to do in the area, and drive or walk around each new location just to see what catches your eye.
11. You’re in ‘the good ol’ days’.
This isn’t to say other seasons of life won’t also be “the good ol’ days”, but if you’re feeling pulled to work from the road while traveling… and you stick with it long enough to figure out what works for you and cross a few bucket-list destinations off your list…
You’re in the good ol’ days, and you probably know it.
It’s easy to get caught up with everything you still want to see, and it’s even easier to question whether you should be spending your time and money traveling (or if you should be investing more, working more, putting down roots, etc.).
However, when you take a moment to reflect on what you’re doing and all of the experiences you’re having, it’s pretty spectacular. Regularly give yourself credit for making this happen and making a dream come true!
12. Ultimately, working from the road is not THAT different than working remotely from a home office.
The biggest thing to know about working from the road is… It’s just not that different than working remotely from a home office.
Sure, there are tradeoffs (see #3) and often challenges (see #4), but all things considered, working from the road is still just remote work. And you can do remote work at home, too.
So, if you can do all of your work from a laptop or desk monitor and phone (utilizing software like Slack, Zoom, and Asana for communication and meetings), then working from the road isn’t that big of an adjustment.
As long as you can find a quiet space to work with a good connection for calls, you’ll be just fine! (And even when you can’t, or you have to get creative by taking a call from a closet or your car, it’s probably going to be just fine and makes for an interesting story.)
Whether you’re full-time remote or working a hybrid schedule, consider taking a few days to work from the road in a new location and see what you think. You might be surprised by how much you love the flexibility to explore different areas outside of work hours!
By far my favorite on-the-road office to date! We spent two months in the mountains of North Carolina working from this large kitchen table surrounded by floor-to-ceiling windows.
My most common setup on the road. With the portable stand, I can stand or sit using a counter-height chair or stool.
If this was helpful, please share!
If you found this guide to working from the road helpful, please share it on Pinterest (you can pin any of the images above), Instagram, or Facebook.
We share new blog posts every Wednesday. To receive these in your inbox each week, please scroll to the bottom of any page and subscribe!
Comment below: What else is important to know for working from the road?
If you work from the road, what would you add to this list? If you’re planning to work from the road, which of these do you find most helpful? We’d love to hear from you in the comments below!