11 Truths About Traveling While Working

Jonathan and I have been traveling while working since 2019. We spend up to 6 months each year on the road while working full-time. While writing this post, we’re in the middle of a month-long stay in the Canadian Rockies. (A dream location!)

Traveling while working is one of the best things we’ve done, and in the back half of this post, we’ll share what we love about this lifestyle. But since the “good” of traveling while working is generally what’s most shared, the first half of this post is dedicated to the less shiny truths… i.e., the tradeoffs of traveling while working.

It’s still worth it, and this is not meant to be a post complaining, but rather we want to be honest in sharing our truth about traveling while working full-time. So, let’s go!

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Next: 12 Things to Know About Working From The Road

1. Traveling while working can be exhausting.

… And 70% of the time, it doesn’t actually feel as glamorous as it might sound.

Friends tell us they love sharing what we’re up to and ask us questions about how amazing it must feel to be exploring so much.

The truth is, it is amazing, AND it’s exhausting. It’s also normalized to a degree for us so that we’re not exclusively living in the mindset of “this is incredible”. It is incredible, but just like most of us in various situations, we still have to be intentional about practicing gratitude and reminding ourselves how special it is to travel while working.

We often feel “full,” in a good way, but because we’re juggling work deadlines and career aspirations with travel plans and lots of things we want to do and see, it’s also easy to feel overwhelmed.

Our favorite stays are long-term stays - about a month - because that’s the best length of time for us to explore much of what an area has to offer without feeling rushed to go go go every day after work.

And also, we’ll just throw this out there right away… You know those pictures that pop up when you Google “traveling while working” and see dozens and dozens of images of people working from a laptop on the beach? Yeah, I’m not sure who those people are, but that’s NOT us. We’re not even the people in the image at the top of this post working from a van. (Not yet, at least 😜)

We both work full-time; Jon’s a Business Intelligence Manager, and I’m a Copywriter. While we *might* spend a few hours here or there working from a park or the car, we’re mostly in a hotel room or short-term rental. (If we’re craving outside time, we might work at a picnic table or patio table… outside our unit… in the shade.)

We definitely require a more traditional work setup for the ~40 hours a week we’re working, and our backs would hurt in about two minutes if we tried working while lying down at the beach. Just saying!

2. It’s also probably not the most financially wise decision.

I don’t want to say this is always the case because there are definitely situations where traveling while working can be less expensive than a traditional mortgage or rent in certain cities.

However, we travel in seasons, so we spend the “Basketball Season,” from November to early June, in Dallas and spend the rest of the year, our “Travel Season,” on the road. We have a home base we’re not able to short-term lease in Dallas.

And because our work requires reliable internet and regular meetings, it’s made more sense for us to stay in short-term rentals and hotels rather than campgrounds or RV parks. We’ve budgeted to make this possible, so it works for us, but it’s definitely not the most financially wise decision we could make.

We often wonder if there’s a better way to travel while working and regularly consider an RV or camper, but also wonder if there’s a different way we should be spending our money right now, such as through investments.

Ultimately, we choose and love this lifestyle, so it’s the right choice for us, but that doesn’t mean it comes without financial tradeoffs.

3. We miss out on stuff.

This one just goes with the territory of traveling for an extended period of time. We miss out on things, like our nephew’s birthday party, a friend’s wedding, baby showers, and family dinners.

Sometimes we’re able to make it to these special events, and sometimes our travels take us to the right area at the right time. But often, we have to say “no” to seeing friends and family as much as we’d like, or we won’t get invited at all because people don’t want us to feel pressured when they know we can’t be there.

This one’s tough for us, being on the road so much, and we often wish there was a way to teleport ourselves to friends and family events for an evening here and there! Of course, we could fly in for a weekend, and sometimes we do, but traveling with our pup Lincoln makes it challenging to get to various destinations quickly.

We never really see anyone talking about this, but we definitely miss out on a lot of things traveling while working, and that can be hard.

4. We feel pulled in a lot of directions.

Similarly, we feel pulled in a lot of directions traveling while working.

There are approximately 147 things you want to do in a new area and approximately 147 things you have to do for work.

From checking in and investing in time with friends to working our jobs and progressing our careers to traveling and experiencing new things… We often feel pulled in a LOT of directions. This can be stressful as we hope we’re doing enough in every bucket but are almost always aware we could be doing more.

It’s like when you’re full after a delicious meal… It’s a good thing, but sometimes it’s uncomfortable to be too full. We can find ourselves feeling that way as we try to balance work, travel, and life.

5. ‘FOMO’ doesn’t go away.

You’d think traveling beyond a three-week vacation would feel epic all of the time. Because… wow! You’re doing and seeing so much!

But the truth for us is… There’s always another level of traveling while working and ‘FOMO’ doesn’t go away just because you’re traveling more than you were before.

Not only do we regularly meet people who show us how we could take our travel up a notch — whether that’s backpacking through a remote national park, living full-time out of a van, or working 4-day work weeks — but we also come across more incredible things to do in an area than we ever have time for.

As we travel while working, we have to make decisions about how to spend our evenings and weekends… and we have to remind ourselves that what we’re doing is dang cool, even if there’s always another level to take it or one more thing to see.

6. It’s hard to eat healthy on the road.

It’s generally challenging to eat healthy. But on the road, we find it even harder.

This is something we’re still learning how to do, because convenience and ease generally win on the road. There’s also so much we want to explore in an area and that includes local restaurants, breweries, and cideries. So we have to balance our desire to try new things with our desire to stay healthy as we go.

And that’s sometimes challenging for us!

It helps to book places with a kitchen and generally eat at least two meals a day at home (plus spend two to three nights a week in), but again, there are lots of great restaurants we want to check out. And since we’re often tired after a full week of traveling while working, we don’t always want to cook.

We have to be really intentional about convenient, healthier options, things like veggie trays, veggie pizzas, frozen veggie medleys with olive and rice, rotisserie chicken, and smoothies. Things that don’t go bad quickly and can provide us with some nutrients without too much work.

The same goes for keeping up with a gym and fitness routine on the road. We love booking hotels with a gym, we make a point to find trails great for trail running, we do a lot of hiking, and sometimes we bring our ‘Gorilla Bow’ to work out on the road.

But even when we have options for working out, we generally feel like we’re balancing a full-time job with full-time travel, which means something has to give, and the length and quality of our workouts generally do.

7. We wear the same things day after day.

Or in other words, we don’t feel the cleanest (or the most trendy) most days of the week. (And I’m sure our coworkers have seen us wear the same outfits on video calls time and time again!)

It’s helpful to pack light when traveling while working, especially if you bounce around a lot like we do and try to see many places. Merino wool is your friend for this, as it’s a great fabric that requires fewer washes between wears. (It’s good for odor resistance.)

But even if you don’t smell (and let’s be honest, you will sometimes), wearing the same thing day after day gets old and doesn’t make you feel the cleanest or most put-together you’ve ever been. (Particularly when you’re wearing the hoodie or the pants you wore yesterday and most definitely sweat in while hiking.)

This is definitely a tradeoff worth making, but it is still a tradeoff, and you have to be okay with not wearing exactly what you want to wear most of the time. (Because you can’t bring your favorite pair of going-out jeans and your most comfortable pair of jeans and your favorite Sunday morning sweater and the sweater that can double as a date-night outfit, etc.)

Okay, so there are definitely some less-shiny truths about traveling while working, but if you can accept these tradeoffs, this lifestyle rocks. Pinky promise. So let’s chat about things we love experiencing as we travel while working!

8. We don’t have to wait for vacation days or retirement to cross bucket list places off our list.

This one’s pretty self-explanatory.

Before we started traveling while working, we didn’t take a week-long vacation for multiple years. (In fact, we canceled two different vacations to take new jobs.) Now that we travel while working, we not only explore on evenings and weekends, but we also take more vacations as we find ourselves in areas we want to explore more deeply.

As I’m writing this, we’re spending a month in the Canadian Rockies visiting places on my bucket list, such as Lake Louise and Moraine Lake, Jasper National Park, and the Icefields Parkway. Last weekend, we spent our Sunday tackling a Via Ferrata at Mount Norquay overlooking the town of Banff. Like… What!? 😱

And next week, we’re spending a night in the Fairmont Chateau Lake Louise, and I can hardly believe I’m writing those words as this stay has been on my wish list for as long as I can remember.

9. We feel like we live in many different places each year.

This is one of my favorite things about traveling while working!

Jonathan and I have realized something about ourselves over the last few years: We love change. Like, a lot. But we (and especially me) also love stability. Traveling while working, but also having a home base where we spend half our year, has given us exactly that.

We get a lot of change for months each year. We bounce around between sometimes dozens of locations. But our favorite length of stay is a month-long stay, so we have time to settle into a new location and feel, even if for a short time, like a local. And because we’re working while we travel, we really do feel like we’re living in these different places.

We find favorite trails or parks to walk our dog, Lincoln, before work.

We find favorite local restaurants and breweries.

We fall in love with a coffee shop or ice cream shop down the road.

It’s so much fun to temporarily see what it’d be like to live in a new area, and it’s fun to know we’re heading somewhere new in just a few weeks. Because we get to experience so many different things AND knowing we’re on the move soon makes us want to get out and explore as much as we can!

…And who knows, maybe one day we’ll find a place we love and just never want to leave… :)

10. It’s fun!

Truly, traveling while working is just fun.

The things we get to see.
The adventures we have.
The memories we make.

We’re exploring dozens and dozens of beautiful places all throughout the United States and Canada, and it’s just a lot of fun to regularly have new experiences and see new areas together.

Whether it’s going to a cidery after work, camping in a national park, or road-tripping one of the most scenic drives in the States, our evenings and weekends are often full of neat things we love!

11. It expands our perspective.

Another one of my favorite things about traveling while working is how much it expands our perspective on what’s possible (and how much still we’d love to see).

I feel really fortunate to meet new people and regularly expand my thoughts and beliefs on ways of doing things or lifestyles available to experience. As mentioned, there’s always another level of traveling while working, and it’s been really great to stretch ourselves to dream bigger and bigger!

There’s a quote Jonathan brings up often.

“First, I had time, but no money; then I had money, but no time. Finally, I had time and money, but no health to make use of my wealth.” – RVM

This is something we often remind ourselves. We feel so fortunate to have the time, money, and health to experience so many new and beautiful things as we travel while working!

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