Expert Insights On Working Remotely While Traveling

It looks like remote work is here to stay, a lot of Knackpackers are wondering what it’s like to work and travel at the same time. Is it affordable? Is it worth it? What are the challenges? 

There’s no one more apt to tell us about how to work remotely while traveling than Nora Dunn, author of The Professional Hobo travel blog. Nora’s been traveling full-time since 2007, when she quit her job as a financial planner and found herself writing her way through 60 countries. Her content is incredibly helpful to anyone who wants to get started in traveling while working remotely.


working remotely and traveling

Nora’s on another adventure at this very moment, and with her Knack in tow (which she reviews here). 

"I’m currently on a 3-month carry-on only trip and I’m using my Knack bag as my 'personal item'! It’s great for trip flexibility; unexpanded it’s the perfect size for “personal item” when flying, but the expansion allows me to get a few things while I’m on the road that I might not otherwise have room for." 

Here are some of Nora’s insights into working and traveling at the same time:

What's your experience with remote work and travel?

"Not to sound like some crotchety person yelling 'get off my lawn!', but I was working remotely before it was even 'a thing'. I started traveling full-time and building a remote career as a freelance writer and content creator back in the pioneer days of 2006. This also makes me one of the 'OG' travel bloggers, which is pretty funny because people who know me wouldn’t call me a leading-edge kind of gal. But I was in the right place at the right time! 

Now, I’m paying 15 years of remote work and travel experience forward, helping newly minted remote workers and aspiring long-term travelers wade through the maze of logistics and lifestyle nuances so they can travel long-term and work remotely in the most effective ways without having to contend with the inevitably steep learning curve involved. I do this with instructional and inspirational content on my site, my Remote Work & Travel Show, a podcast (coming soon), personal coaching services, online courses (in development), books, and speaking."

What's the best part of working and traveling at the same time?

"You know, it’s funny. Most people who work and travel at the same time are living the dream - I’ll make no bones about it. But for most of us, if you explicitly put the words “working and traveling at the same time” together in a sentence, most of us will start thinking about the challenges, which are mainly around work-life balance and setting a pace of travel that is maintainable in the long run. It takes a while for each person to find their groove of work and travel. It’s different for everybody; for me, I like to set up bases for at least a few months so I don’t feel rushed or torn between my need to work and my desire to rush out and “discover” my destination. 

 But nestled in these challenges of achieving an optimal work-travel balance, is the gem itself - the reason we do all this to begin with. I get to call all the shots! I choose what horizons I’ll explore at the end of the work-day when I close my laptop. I decide where and how I’m going to set up my office on any given day, when I’m going to work, and what my travel lifestyle is like. And I can change any element of how I design my work and travel lifestyle at any time. In the last 15 years I have designed and redesigned (and redesigned again!) my life and lifestyle to it could suit my needs and desires along the way."

working remotely while traveling full time

Every day's an adventure when you work remotely and travel, but does the lack of stability make it harder to be productive?

"Absolutely, it can. That’s why I ended up setting a pace for travel that is slow. 

Travel itself is like a job. You have to select your destination, research it, figure out how to get there, where to stay, book tickets, etc. Then you arrive and have to figure out how to survive there; how to get around, buy groceries, etc. If you only plan to stay there for a month (a common rookie mistake is to assume that’s a lot of time), then as soon as you’ve figured out the basics of the place, it’s time to start researching the next place! It’s exhausting, especially when traveling solo since there’s nobody else to split that work with…and you’ve got to continue working full-time."

Want some more tips on working from anywhere? Check out this blog.

What do you keep on your laptop as you work remotely?

"Working remotely requires self-discipline and organization. As a remote entrepreneur, I keep myself on track with Asana for task management (and team member delegation), and I adore using LastPass to not only generate and auto-populate ridiculously secure passwords, but also to share my log-in information with team members without ever actually having to share the passwords themselves. Lastly, a VPN is critical when working remotely from any kind of public WiFi connection (even if it is password protected)."

Traveling for business? Get the Ultimate Guide To One Bag Business Travel.

You've wisely said that "The weight of your luggage is equally proportionate to your level of misery on the road." How do you decide what to bring - and what not to bring - with you on a trip?

"Great question! When I traveled full-time there wasn’t much choice since everything I owned went into my bag! Though the curation of each and every item I owned was both art and science, to maximize space, weight, and utility. 

Now that I have a home base (and a closet full of different types of luggage!), I pack specifically for each trip I’m taking - even if I’m not sure exactly where I’ll be going or how long I’ll be gone! I pack according to destination, climate, activities I expect to participate in, and length of trip. If I’m going to one place for a few months, I’m more likely to take checked luggage with some items that make my time there more comfortable or effective, like a travel yoga mat and dedicated hiking shoes. 

If I’m going on a shorter trip or I’m moving around a lot, then I’ll usually choose carry-on luggage for ease of packing and getting around.

Here’s a really handy set of criteria you can use to determine whether your next trip should be with checked or carry-on luggage!"

work and travel

Thanks, Nora, for pioneering a life of work and travel, and for sharing it with us. 

By the way, if you’d like an expandable carry-on backpack like the one Nora’s traveling with, then check out all of our Knack Packs here.


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