Have Online Job, Will Travel: But Is It Worth It?

Have Online Job, Will Travel: But Is It Worth It?

Confession time: we regularly ask ourselves if a nomadic lifestyle is worth it if we still have to work full-time.

From the outside, a traveling lifestyle looks pretty darn carefree, even if you have a job as you roam. This belief is perpetuated by travel bloggers (ourselves included!) posting jealousy-inducing photos of themselves working near the beach, in swanky urban locations, at adorable coffee shops, and in other idyllic conditions. Work shouldn’t be nearly as stressful if you’re always in new, exciting, beautiful places, right?

What we don’t post pictures of is an aspect that can be far less glamorous, and even downright miserable at the worst of times: staying online ~40 hours a week while moving about the world in a constant state of unfamiliarity and upheaval.

We’re among a fast-growing group of full- or part-time nomads who are young enough to need to work “normal jobs” to offset our basic survival needs, pay off student loans, plan for retirement, and cover other financial responsibilities. Most working-age nomads will debate from time to time whether it’s worth it to live this way, especially during a particularly stressful segment of travel.

Everyone’s answer to this question will be different of course, but here’s ours:

Most of the time it’s completely worth working and traveling simultaneously – but at times it can be ridiculously hard, and tempting to go back to a fixed location.

Here are some challenges we plan ahead for while working and traveling:

Connectivity’s a b!tch in a lot of places!

There are times when cellular data or wi-fi speed is so weak or non-existent that we find ourselves longing for a fast landline connection and can only dream of bingeing on Netflix and cat videos. We miss not having to think about things like whether we can handle video conference calls, download a large file, or access a VPN or proxy connection and regret that we completely took for granted the insanely fast (by comparison) internet speeds we had living in a fixed location. We think back to the “good old days” when we had no data cap and didn’t worry about cellular towers overloading from large crowds or bad weather affecting our reception.

This summer has been so tough for internet, in fact, that we’re considering doing multiple-month vacation home or apartment rentals pretty often when we get back to the lower 48, just to recover from the stress and cost of finding a usable signal in Alaska and Canada these past few months. There was nearly always an inverse relationship between the beautiful areas we wanted to spend our time in and those that had workable cellular data speeds. We spent far more nights in parking lots or crowded campgrounds in urban areas than we had hoped to. We currently have SIM cards activated on four different cellular carriers. Yes – FOUR!

This is a stressful day for a digital nomad.

We’ve often had to travel further than we’d like to get back into cell phone coverage areas, stay in a location that’s not at all glamorous but more practical for working, drop a bunch of money on drinks and food to hang out all day at a business with wi-fi, or reschedule work meetings or deadlines – which is our absolute last resort when we can’t make any of the other options work for us. We try to never let our travel negatively impact our work if we can help it. If it starts to interfere, we stop moving for a while or get ourselves to a place where we can find more consistent internet. The silver lining is that with every passing year, technology improves and connectivity gets easier. We have it so much better now than we did even a couple years ago, but we have a long way to go while keeping our fingers crossed that someday it won’t even be a consideration in planning where to go next.

Work while traveling
We have to make a concerted effort at striking a healthy online/offline balance, since we do have to stay connected so much of the time

Uncontrollable surroundings

If you need consistency while working, this may not be the lifestyle for you – at least not long-term, or without some pauses in there to establish a routine and rest. When you compare constantly adapting to new environments versus working in a steady home or commercial office environment with almost guaranteed internet speed and the ability to control your surroundings, a traveling office is far more disruptive, especially if you have an already-stressful job.

If you’ve ever worked in and around public places, you know that getting knocked out of a work rhythm by interruptions can make productivity difficult or downright impossible. We battle distractions a lot, whether it’s people dropping in on us during work hours, noises like car alarms, children playing, barking dogs (but not usually our own dogs – they know when we give them “the look” that they’d better quit!), planes/trains/trucks/boats, and sometimes even each other when we’re both trying to have calls at the same time.

Fortunately, there are some options for those times when good internet and peace and quiet are a requirement: co-working spaces are popping up everywhere, there’s libraries, book stores, coffee shops/restaurants/bars (noise canceling headphones help here), moving to a secluded spot that has good cellular reception, or renting a house/apartment/hotel room when you need a longer period of working without distraction. Regardless of our level of burnout after this big trip, we plan to do frequent multi-month vacation home rentals in the coming years, just to give ourselves some time to crank out some work and regroup amidst our wanderings, and to dive deeper into some locations we’ve found that we really like or want to visit for the first time. We do miss feeling like actual locals at times and having some familiarity with an area that only comes with staying there a while.

A coffee shop or other public place is not always a good environment for productivity that requires concentration…unless you have great noise canceling headphones! If concentration isn’t vital, social energy and activity buzzing around you can be uplifting, spur creativity, and pull you out of a work funk.

Avoiding the vacation/retiree mentality

While we have some freedoms that most office workers don’t, there are certain times that work still feels like a burden – just like it did when we were office workers and wanted to be elsewhere, enjoying a particularly nice day. Many of the places we travel to are also popular tourist spots, which means that we’re surrounded by people on vacation…while we’re very much not.

It’s nearly impossible to avoid comparing ourselves to people nearby who are on a holiday or retired, and to not feel like we’re missing out on lots of fun because real life is getting in the way. We’re constantly reminding ourselves that vacationers are going back to their “real lives” soon, while ours just travel along with us. We get to stay in some amazing places as long as we want, spending enough time to do more than a tourist could, just at a slower (and often more enjoyable) pace. Remembering that we’re at least thirty years younger than most of the retirees we meet helps put into perspective that working hard is worth the tradeoff of doing this earlier in our lives.

As a working nomad, it’s so important to prioritize what you want to do in an area you visit and be realistic about how much time and money you should spend to experience that place, especially knowing that work will be taking up a sizable chunk of your time. Allow yourself to miss out on some things so you’ll want to come back again, and if you don’t ever plan on being there again or are unsure if you’ll return, just allow more time to do everything you want to at a reasonable pace.

Unlike most of the people visiting that location, you’re not on a week- or two-week-long vacation that only happens a couple times a year, so take your time, be discerning, soak it in your own way, and don’t feel pressured to do it all. It’s never worth just seeing everything quickly, versus experiencing a few things you’re passionate about to a deeper degree. We can easily slide into that bad habit in a new-to-us place, like here in Alaska where we know we only have 3 months to “see all the things!” We often have to rein ourselves in and slow the heck down or we’ll leave exhausted, disappointed, and with a lot less money than when we arrived!

go slow sign

Finding your tribe

While it can be difficult at times when you’re new to an area and know no one, one of the best things we’ve done to combat feelings of isolation while working on the road is find and reach out to other working nomads, and meet up when possible. We tend to form a support group of sorts, sharing our struggles with work/travel balance.

There are days when it almost hurts to take a stroll around a beautiful place and see vacationing people enjoying their lazy days, knowing we have to get back to work. It helps to be around others who have similar work schedules and plan some fun group activities as a reward during mutual time off. We love to befriend people who don’t work too, but it can be hard to plan things together since we keep somewhat consistent weekday work hours and they tend to plan their activities during the day.

Meetup of younger bloggers in Alaska at a baseball game
Meet-up of younger full-time travelers and bloggers in Fairbanks, Alaska at a baseball game – Snowmads, Gone with the Wynns, Technomadia, Tales from the Mutiny, JenEric Ramblings, The Learning Banks and Ardent Camper. It’s so great to share experiences and stories with others who live a similar lifestyle! Photo courtesy of Technomadia.com

So what are the benefits then, if it often sucks to work and travel? Well, in our minds there are still far more positives than negatives..

Non-Work Time is Far More Adventurous

When your office view changes often, so do your leisure activities. While it’s still hard to get motivated some days to work when there’s so much we’d rather be doing elsewhere, not losing an hour or more a day to commute to work means that after we get a half a day’s work done, we reward ourselves with a break for a couple hours in a place that’s usually new and exciting to us – a micro-adventure in the middle of an otherwise typical work day! It’s amazing what a good stretch and change of pace mid-day, plus the novelty of a new location, can do for mental and physical health.

Our free time is also no longer limited to just nights and weekends. If a local farmer’s market is happening Wednesday afternoon, we’ll take a break then to visit it and then get back to work after. Going for a hike on a weekday is much more pleasant than on a crowded weekend. Having that kind of flexibility means we can make plans that allow us a buffer for weather too – we stay somewhere for a week and pick the nicest weather days to go out and do some things, then work or take care of personal errands and chores on the days that aren’t so nice. That’s been the best thing about not just the nomadic lifestyle, but working at home in general. Being a nomad takes it to a new level, though, and our recreation is often at National Parks or in exciting cities we’ve never explored, rather than just our neighborhood or local trails.

We can grow professionally by incorporating work into travel..and vice versa

As we roam about the world, we make an effort to meet up with a variety of people who can help us grow and stay sharp professionally: reuniting with former and current coworkers and clients, attending conferences to learn new skills or meet others in our fields, and arranging co-working sessions or just casual meet ups with other working nomads or people living in places we visit. The line between work and life is very blurred for us to begin with, so we don’t mind spending some of our free time “talking shop.” Being receptive to these opportunities while traveling has opened up countless doors professionally and personally, and any chance we can get to help someone or learn from them helps us avoid career complacency or burnout.

Living in the “now” instead of the “someday” makes us better workers

The biggest change we’ve seen in ourselves the past two years is that we have far more of a focus on living in the present, which stems from chasing some of our dreams now, instead of saving and hoping for the ability to travel someday. Time rushes by far more quickly than you’d like when you’re dwelling on the past or future.

When we worked traditional go-to-an-office-everyday jobs, we always daydreamed that we were on vacation. When we were on vacation, we worried about our work back home. Now these two sides of our lives are so closely joined that we can change from work to play as fast as we can close our laptop screens, which means that we can live more in the moment and dedicate ourselves fully to what we’re doing at the time. Sure, we still look forward to the end of our work day (who doesn’t?) but we don’t daydream the day away or waste time surfing the web, because when we finish our work and log off for the day a real-life adventure often awaits.

It makes sense that since we’re not the gambling types in a casino, we also don’t want to bet on what our future will bring. Someday we or our family members’ health may not allow for traveling, we might lack the money, or our careers could change and prohibit it. Not realizing this dream while we have the opportunity would always leave us wondering “what if?” Living and planning for happiness only in the future instead of in the moment isn’t truly living, and that goes for whatever it is that makes you happy – whether that’s travel, education, career, hobbies, family, or other areas of your life. As morbid as it sounds, none of us are guaranteed a life long enough to wait for retirement to do what we love.

We prefer to take the carpe diem approach around here. Whatever your “thing” is, why not start doing it now instead of waiting, even if it’s baby steps or a little bit of a compromise if you can’t jump in fully? The timing is never perfect. We’d obviously prefer not to work, or work a lot less, and just enjoy travel full-time, but this is a far better alternative than not doing what we love at all!


Looking for more information on what technology we use to stay online while we travel? Try this article!

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  1. Jul 21, 2015 / 3:49 am

    Great honest article. We are planning on hitting the road in 2016 with excitment and apprehension. We have decided to try to make some money while traveling and are in the process of working that out. Your article gives us alot to think about.

    • Kristin
      Jul 21, 2015 / 12:20 pm

      Thanks, Diane! Best of luck with your adventure and please let us know if you have further questions – we’re happy to offer our experience and share resources that helped us!

  2. Jul 21, 2015 / 4:03 am

    Awesome post! I can sooo relate!

    • Kristin
      Jul 21, 2015 / 12:18 pm

      Thanks, Cheryl! We nomads definitely have a new appreciation for fast internet, don’t we? At times it’s like a tall, cold glass of water after wandering the desert for days! 😉

  3. Nancy
    Jul 21, 2015 / 4:37 am

    Great article. My husband and I spent six weeks touring around the Southeast this past spring. I thought only Vermont, where we live, because of the mountains, had sporadic good cell reception. Not true. As soon as you are away from a populated area, cell reception tends to provide only one or two bars

    • Kristin
      Jul 21, 2015 / 12:14 pm

      Thanks, Nancy! We’ve been surprised at the types of places we couldn’t get cell service. We can be in the desert and have great access, but some of the major metro areas’ towers are very overloaded, and we had poor service in those areas. In Alaska, every time a cruise ship comes in it crashes the network. It’s definitely a challenge at times, but still worth it most days! 😀

  4. Jul 21, 2015 / 4:51 am

    Great article Kristin! There are so many people that aspire to a lifestyle like yours and this article puts a bit of balance into the equation. It is an awfully exciting life though… and I think this should give your readers even more confidence to give it a try. -Russ

    • Kristin
      Jul 21, 2015 / 12:12 pm

      Thanks so much, Russ! I hope we can encourage more people to work through their fears and try something they’re passionate about. I hope you guys are having a great summer and enjoying some trips in your Travato – give our best to Kathy! 🙂

  5. Jul 21, 2015 / 5:06 am

    Great and honest blog! As retirees, we applaud you and wonder how you do it….all the while wishing we had done this much younger. We’re appreciative we’re in good health and can be on the go, and still hike easily….but we still feel our “age!”

    • Kristin
      Jul 21, 2015 / 12:08 pm

      Haha – thank you, Debbie! We wonder how we do it some days too… 😉

      It would have been a lot harder to do this when more than just a few years ago, though some people still managed. We’re so lucky that technology is as good it is, even though it can still be lacking at times, and that we can take our careers with us instead of walking away from them. That doesn’t mean there aren’t still days when we wonder if retirement isn’t a better time for this kind of craziness! Safe travels and we hope to cross paths again soon!

  6. libertatemamo
    Jul 21, 2015 / 6:10 am

    Great blog post with a very balanced and honest view of what it takes to work on the road.

    • Kristin
      Jul 21, 2015 / 11:42 am

      Thanks, Nina! We’ve met more and more people lately who have also taken more traditional working hours and higher connectivity needs on the road, so it felt like as good a time as any to write this while the struggle is so real here in Alaska. 😉 Sending our best to you and Paul, and can’t wait to see you guys again soon! We’ll be back in Oregon in September if you’re still around the PNW.

  7. Barbara
    Jul 21, 2015 / 7:01 am

    Thank you for such a well written article! I can relate and discovered recently just how hard it is to try and work while traveling in an RV. I thought going into it would be challenging but like so many things in life you don’t “really” understand until you are actually trying to do it. It is difficult!

    Thanks again!

    • Kristin
      Jul 21, 2015 / 11:37 am

      Thank you, Barbara! Nothing worth doing is ever easy, right? 🙂

  8. Cherie - @Technomadia
    Jul 21, 2015 / 7:40 am

    It honestly takes time to get into a balance that is sustainable.. and even after 9 years, we sometimes struggle with it still.

    Switching up modes of travel like we have over the years, and so have you (by changing RVs, etc.) takes away from that time of finding your rhythm. So does going off on a big ambitious adventures that take you away from the things you need to sustain (ie. internet). The planning and transition points can be exhausting, and so can’t the big repositioning. We definitely just have to force ourselves to be in one spot for a while, or forgo some adventures. But but but.. it’s a big world out there, and so much to see!

    After our 2 months on this non-RV Alaskan adventure of constant motion.. we’re feeling it ourselves.

    It is totally possible to overcome a lot of these challenges however, and mobile internet has gotten tremendously easier. For our work life, we’ve moved away from income sources that require us following anything resembling a schedule – being ‘on call’ for certain hours was mentally draining. It’s been so freeing to finally get there. Maybe there’s hope for this balance thing?

    • Kristin
      Jul 21, 2015 / 11:36 am

      Such great insight as always, Cherie – thank you for serving as a nomadic mentor to us in addition to being such a dear friend!

      I agree that changing forms of travel does take away from rhythm..but we also have been very ready for the change each time, so maybe we’re just gluttons for punishment? 😉

      This summer definitely taught us that spacing out the bigger adventures, like a full year between these huge trips requiring lots of miles of driving, is probably best for our productivity and well-being. Having just repositioned from east to west then south to north in half a year was far too much, even for us crazies, especially having missed so much en route in our rush to make it at the best time of the season to be in Alaska. In the future we’ll space out our repositioning and dive deeper into the areas we’re already in before moving on.

      We’re so thankful that we love our current jobs and actually enjoy the more regular schedule we have now than when we did project-based work – it’s easier to plan our lives around the expected than the unexpected in a lot of ways and having to stay nearer civilization is a small price to pay. I think we’ll find our ideal balance soon. Now that we’ve scouted most of North America and narrowed down our happy places we intend to spend a lot more time in them! 😀 Happy travels back to your home! We can’t wait to see it in person when it’s done.

  9. Jul 21, 2015 / 7:42 am

    Great post. I can totally relate to the sometimes frustration of working on the road. Sometimes it seems I finally get myself together only to have lousy internet for a week. I am 50, but I still have to work and am doing what I love. That’s why I follow you younger technomads, because you inspire me and I learn so much from all you guys!

    • Kristin
      Jul 21, 2015 / 11:22 am

      Thanks so much! We’re glad to help inspire because we’re equally inspired by anyone, regardless of age, who’s out there doing what they love too! We learned from those who blazed the trail ahead of us and hope to pay it forward by encouraging others to follow their dreams. Happy travels!

  10. Jul 21, 2015 / 8:21 am

    We are part-time full-timers – we have a home base and travel for extended periods of time each year (previously in our SUV, now in an Airstream). Working from the road does sometimes have its struggles, like internet access and feeling cooped up in a beautiful place. When I feel frustrated with those things, I do try to put things in perspective. Even if we have to work while we are traveling, our lives are much more fulfilling than they would be if we were grinding away at home. At least in our case, having a home base does provide a release valve that we need – a place with reliable internet, big monitors and desks (we are photographers) and a place to just stretch out. I hope you two are able to find the same balance by staying put for a bit so you can be rejuvenated for your next phase of travel.

    • Kristin
      Jul 21, 2015 / 11:20 am

      Thank you, Sarah! We can’t agree more that work is more fulfilling with some travel thrown in, even on the worst of travel days. We look forward to borrowing some “home bases” though so we can have an office set up that we don’t have to tear down every day, real furniture, a yard for our dogs, and more space to cook, entertain, and relax for a while. I can guarantee we’ll get the wanderlust bug after a few short months though, and be back on the road with renewed enthusiasm for it! Happy travels! 🙂

  11. Jul 21, 2015 / 8:33 am

    Great article about the realities of Internet access and how days are spent. It answered questions I had, and was especially timely for me and my wife, who plan to hit the road in a couple of years, traveling and working virtually on the road. As a visual designer, I’d need good high-speed access. Your suggestion of Co-Working spaces is great — places I’ve used locally for work, but something I hadn’t thought of to help with FT RV living and working. I sure hope many more pop up all around the country, and high-speed wireless service becomes available in more places.

    • Kristin
      Jul 21, 2015 / 11:11 am

      Thanks, Carlos! An important thing you noted that we may have glossed over is how much your experience can vary based on your type of job – if you need true high-speed access that’s reliable (we have to stay connected to a proxy for long periods of time, for instance) then co-working spaces, RV sites for a month+ where you can have a cable internet line activated, or areas with kick @ss cell coverage are the best bet. It’s just too stressful to meet your work obligations otherwise, and enjoyment of travel starts to suffer. One of the best pieces of advice is buy an RV that you think is easily maneuverable, because you’ll spend a lot of time driving it around looking for good internet! We’re looking at vans and small trailers next so we can spend more time mooching wi-fi at the homes of friends and family. They like getting to see us too, so it’s a win/win. 😉

  12. Jul 21, 2015 / 1:26 pm

    Very honest and detailed post about working nomadic life. My husband and I are “semi-retired” taking a few years off work rather than waiting for retirement although it is not too many years away. “Tomorrow is promised to no one”. The internet, though access may be challenging at times, has opened up such possibilities for people to work while on the road – it is a different world. May you continue to enjoy your lifestyle to its fullest!

    • Kristin
      Jul 21, 2015 / 3:26 pm

      Thanks, Brenda! Your method sounds like a great way to do it, too! Enjoy your travels as well and happy countdown to retirement. Hope to cross paths with you guys someday. 😀

  13. Jul 21, 2015 / 3:21 pm

    We rented a home for 6 months after three years of travel and it was fantastic. That feeling of being a local that you mentioned plus the worry free bandwidth and the time to get to know a place. Highly recommend it, the stay revitalized our enjoyment of travel. I’m sure there are more long term stops in our future

    • Kristin
      Jul 21, 2015 / 3:25 pm

      Thanks so much for sharing your experience, Brent! I hope that renting is the same for us. Variety is such a necessary thing with any kind of lifestyle, and too much of anything – even travel – can become tiresome. Happy travels! 🙂

  14. Jul 22, 2015 / 5:36 am

    Well told! Your experience and knowledge is something people can learn many things from. Most people will never understand how much effort it takes to socially, physically, mentally and finically maintain a free spirit. You guys get it! 🙂

    • Kristin
      Jul 22, 2015 / 1:37 pm

      Thanks, Chris! It’s not as easy as we sometimes make it look, for sure, but totally worth it. Hope you guys are having a great summer! We look forward to seeing at least your other half in Utah this fall, if not you too if you decide to make the trip. 🙂

  15. Ruth
    Jul 22, 2015 / 7:10 am

    Really appreciated this post! We’ve just celebrated 2 years on the road and have not covered nearly as many miles. The challenges with connectivity and work commitments have had us moving at a slower pace, especially after the first 6 months when we realized we were headed for burnout. Love the blog, this was your first post that I’ve read, look forward to going back and “catching up” on some of your other posts.

    • Kristin
      Jul 22, 2015 / 1:34 pm

      Thanks, Ruth – we’re so glad to hear that you enjoyed it! We are a bit crazy moving at the pace we have so far, and are about to slow down for the next couple years. We viewed our first two as “scouting years” so we could find some places we really liked and would want to return to for longer periods of time. We had a blast and met a ton of cool people and are now looking forward to some steady internet for a bit and diving deeper into some local experiences. Happy travels – hope to cross paths someday! 🙂

  16. Jul 30, 2015 / 6:15 pm

    Excellent insight! I’m still trying to work out how I plan to make money on the road when I go full time. It’s the only thing that could derail my plans in fact. Your post helped me narrow down and rule out some options, which is actually helpful in making the decision on exactly how I need to proceed. Thank you!

  17. Aug 10, 2015 / 1:47 pm

    We’re about to head out in our Winnebago – but with less than 3 weeks left, a house to empty, solar, batteries & inverter to install, wifi & cellular boosters needing setup, tow package to TBD, and bunks for the kids to build, we’re a bit stressed.

    We’ll probably load everything up and have to climb over mountains of junk and figure out how to install our electrical and wifi on the way, working out of McDonalds & Libraries, and traveling on weekends instead of seeing cool things.

    Our big mistake is probably setting a breakneck itinerary — Oregon & Washington in September, Florida in December, and California in February.

    Part of this is work-driven …er… driving, so I should probably consider it a blessing that I’m not alone in line at airports and instead can eat sandwiches at rest areas with my family while traveling.

    Hopefully we’ll survive and be able to enjoy next year better.

  18. Nov 1, 2015 / 4:59 pm

    Thanks for the insights, confirmed a few things I was wondering about and flipped the light on in some other areas I’m going to start looking at. Great reading, love your BLOG!

  19. Kim
    Apr 10, 2016 / 8:15 pm

    One place that generally has free internet is a hospital. Strength can vary, but as I generally visit hospitals (for work) and connect via VPN, it generally is okay.
    These are great tips and considerations as we are thinking of travelling more while still working as telecommuters.

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