Working From the Road: One Size Fits All?

While spending the last week in Los Angeles I believe I’ve figured out the secret formula to working on the road. Well actually it’s not a secret, and not really a formula at all, but I’m gonna call it that just because it sounds cool. The Secret Formula!

Anyway it dawned on me during this trip that there are at least three distinct forms of travel, each with inherent benefits and pitfalls in relation to working on the road. By understanding the limitations of each mode of travel, you can effectively anticipate your level of efficiency.

3 Types of Travel

In general, trips can be broken down into three categories:

  • Long-Term Immersion
  • Medium to Long-Term Location Hopping
  • Short-Term Sight Seeing

Now I’m sure you can break it down even further, but these three generally encompass the types of trips that me and Marla embark on.


By far the ideal trip for working on the road is the one that I think everyone dreams of, whether working on the trip or not; that’s immersion. I consider immersion to be any trip of a month or more in which you stay in a single location.

The benefit of immersion is, quite obviously, time. When you’re afforded the ability to travel and completely immerse yourself in a new culture for a month or more, you also have the opportunity to live like a local. While a local, you’ll surely go out on the town and see the sights, but you do so on local time. There’s no need to cram anything into just a few days.

When you want to work on the road, time needs to be your friend, but if you’re not quite on speaking terms as of yet, you better become besties…fast.

The massive amount of time and lowered pressure of immersion lends itself nicely to allowing you to have a bit of structure in regards to your work schedule. I hate over planning a trip as much as the next person, I actually avoid it as much as possible, but when it comes to working on the road some semblance of a structure is vital.

This became ever apparent in Los Angeles.

Short Term Sight Seeing

Prior to leaving for sunny California, I had already planned on cutting my work time down to somewhat of a minimum. While I did plan on getting some work done, I tried to make sure there were no major deadlines during that week.

Eight days in Los Angeles in the middle of the bitter cold Chicago winter was refreshing, but 8 days is not, by any stretch of the imagination, an immersion trip. We had a great time and did many things on our short term sight seeing trip, but 8 days definitely did not afford me enough time to establish a work routine.

Each day of the trip was spent, no surprise here, enjoying our time in LA. Each day we would come home a bit later than planned after hiking down around the Hollywood sign or after sitting in on a hilarious TV taping or after watching the amazing talent at Santa Monica Beach and then we’d spend some time chatting with our awesome hosts. It was a lot of fun, but after a full day there was only time for a little shut eye before doing it all over again.

I know, having a blast on a trip is nothing to complain about, I certainly have not complaints, but this type of schedule does leave little time for work. Each night I’d try to plug away a bit on the computer, answering emails and getting a few things done, but being such a short trip as this one was, spending long stretches of time working would have meant staying up much later than I would prefer. (yes I’m a night person, and yes I’m normally up working all hours of the night at home, but on a trip I have no interest in sleeping my days away.) 🙂

Working on the road during this trip was not a bust by any means, but I have to rank short term sight seeing as the most challenging form of travel when working on the road.

Location Hopping

Not everyone has the opportunity for long term immersion travel, honestly we haven’t even dove into this realm as of yet, however something that’s at least slightly more attainable and definitely easier on the location independent worker than short term sight seeing, is location hopping.

Back in September, we spent 22 days in Europe. We went from London, to Paris, to Venice, to Milan, Florence, Pisa, Rome and Fregene. In the future I plan on going more the immersion route than location hopping, as this trip definitely was, however one unexpected benefit was the built-in work routine.

The trains were our friend in Europe. Traveling from country to country and city to city involved anywhere from 2 to 15 hour travel by train. This meant 2+ hours (generally more) every couple days in which I was guaranteed to have down time (aka focused work time).

Looking back, this was quite ideal. At the time I had thought to myself that staying put would have been more beneficial, however having this built-in down time ensured that we had no possibility of filling those hours of our day with more adventures.

I find, at least for us, that travel closely follows many of the same principles as a to do list. If you give yourself 3 days accomplish something, it’s gonna take you all 3 days to do it. No question. The same rings true for our travel, if we have 3 days to see Paris, we’re going to fill those 3 days with every last sight and adventure that we can come across, while remaining mindful of our experiences of course, but filling that time is simply inevitable.

I believe that the time insensitive nature of immersion travel can help combat this filling of time, but constant location hopping certainly made a strong case for itself and ranks as highly effective on my list.

Plan Accordingly

For those of you fellow location independents, just a little bit of planning can go a long way. Maybe just getting out of the house and heading to a warm climate or climbing into a cozy snow covered cabin is all that you’re looking for and maybe you’re able to swing it so you can get some work done on your trip. However if you expect that you’re heading out on an adventure where you’ll find yourself constantly seeking more and doing more at every opportunity, then maybe it’s a good idea to reconsider working from the road this one time.

Remember that location independence is about the freedom to work from anywhere, not about working from everywhere. If you find that your travels are suffering and “work-you” never relinquishes power, then try unplugging. Being able to work from the road is great, but if you’re traveling but never making any time for yourself, then how much better off are you really? Becoming a prisoner to your work is just as bad whether you’re in a cubicle or abroad.

Do you typically work from the road? How have your experiences been for both short term and long term travel? Let us know in the comments.

8 responses to “Working From the Road: One Size Fits All?”

  1. James Chartrand - Men with Pens Avatar

    The lifesaver method that’s worked with me has been having a routine schedule.

    At the office, I always wake up early, do my work and by 10am, I start to coast for the afternoon. I can work on a project, talk on Twitter or take the afternoon off – my more important work is already done.

    So keeping that routine as I traveled was key.

    From hotels, I’d work in the morning, then have the whole afternoon and evening to do what I’d like. A quick email spot check before bed and I was golden.

    Visiting friends, same thing – I told people on day one about my routine, and they were thrilled with it, because it meant they got to spend the whole afternoon with me with no distractions.

    I felt good, too. There’s nothing worse (for me) than being at an event or activity and stressing that you need to get back to your email or damn, the deadline’s tomorrow and how will you make it fit. I like my travel stress free. 🙂

    1. Jeff Sarris Avatar

      Ya, no question that a routine is the way to go. And being that you’re the master of the morning that’s pretty killer that you can do that on all trips, including to visit friends.

      I wonder if I would survey morning and night people if there’d be a correlation between effective travel work routines. My routine always involves accomplishing things at night (in the morning I’m all but useless and extremely slow to get anything done), but then while traveling the days tend to flow into the nights and take away much of the time that I hoped of using for work (at least on short term sight seeing type trips).

      I know the “easy” fix that I usually hear is to force myself to become a morning person although I don’t believe that’s actually possible. I think working to the strengths of your personal circadian rhythm will always win out in effectiveness over fighting them. Just wondering if maybe my post is very night owl centric. Hmmm.

  2. James Chartrand - Men with Pens Avatar

    I am Master of the Morning. Be afraid. Be very afraid.


    Scientifically speaking, I think people are less night owls than they believe. I also know that you control your mind, and therefore your results.

    So let’s say that you decided somehow that you were a night owl. Pyschology kicks in, and you’ll validate your decision by looking for proof of that, right? You’ll substantiate your claim so as to behave in a way that supports your belief.

    What would happen if you changed your belief? What if you decided that you’re not a night owl and had just adopted behaviors and decisions that allowed you to support that belief? So you start to believe that you’re a morning person after all, just caught in the trappings of old behaviors and useless beliefs…. wouldn’t you start to try to support that new belief?

    “Auuuh, god, I feel like shit this morning… my OLD beliefs are to blame! Look what they’ve done to me!” And so you work harder at supporting your new belief and become a morning person.

    Musing aloud, here, obviously, but wondering what might happen.

    See, I wasn’t always a morning person. I used to consistently go to bed at 2am every day and swore black and blue I loved it and worked best at night and hated mornings and all that.

    Until it started to get in the way of me having a life. And, until life started to show me that staying up all night wasn’t the best idea.

    It took some revamping but… I am the Master of the Morning. (Totally useless at 9pm, though…)

    I’ll admit I’m not up to date on my sleep research and studies, of course. Feel free to shatter my theories 🙂

    1. Jeff Sarris Avatar

      I am definitely all for changing beliefs and affecting behavior. I think that you are 100% true in that vain. However I also believe that there’s a deeper science behind sleep and productivity, specifically in regards to one’s the circadian rhythm.

      Of course I’m not up to date on sleep research (aside from the interesting hacking parts:, but there was a TED Talk a while back that helped to confirm what I understand about circadian rhythms. In it she referenced a study of, what was it, I think it was lobsters, who they transported clear across the world. In the study they tracked the lobsters behavior and noticed a curious situation. At the exact moment of day that the tide would rush in in the part of the world that they were native to, they would quickly scurry up the shore. Even though they were clear across the world and in no danger of the tide sweeping them away.

      Now I know that’s not sleep (and not human), but it is an internal natural body clock of sorts. There was also a study more directly related to sleep in which there was a group of people secluded, basically in a bunker, for an extended period of time with no stimulation from the outside world. No clocks, no natural light. Without any cues as to time of day they found that in general people would slowly shift their waking hours to what was likely (speculated) more natural to their bodies.

      They’re just 2 anecdotal studies, of course there’s nothing concrete that they offer in regards to this, but in the same vain with eating, I believe that trusting in your internal, Primal intuition is the key to health and longevity 🙂

  3. Andy Graham Mobile Office Avatar

    The three types of traveler is good, it is difficult to define simply, this is rather good. I have perpetually traveled now for over 12 years, almost 13. They say, that two out three businesses fail, and people who try to work while immersed is worst, I would guess only about 1 in 50 is able to work from abroad. The problem is the culture shock and the “I am on Vacation” mentality. It take about a year of perpetual travel before a person finally stops living every day as if they are on vacation and planning sightseeing trips. I spend about one hour per day as a tourist, if that.

    Routine is essential.

    2011 is a special year, this year I am quite sure, 98 percent of countries will have the USB wireless Internet modems on a pre-paid basis. Europe and America will still suck, but you can live in South America, Central, Asia and Africa and have 24/7 Internet good enough for in your room.

    I am in Lome, Togo right now, they sell a USB wireless modem, however I am using to connect my computer to a Verizon Global Email account with a BlackBerry Bold.

    The biggest headache of finding a connection is being solved in 2011.

    Have fun, but stop being a tourist, drinking every night, less stimulation and you can succeed.

    The cost of living daily in the developing world is about 15 – 20 dollars, then add on your drinking bill.

    1. Jeff Sarris Avatar

      Thanks for your insight Andy.

      The “I’m on vacation” mentality is definitely one that needs to be overcome, but beyond simply taking a year of perpetual travel I think that comes down more to the escape mentality. At least the way I see it, a vacation is an escape from something in your life, typically work (hence why I constantly use the word travel instead). If you’re in the mindset of a vacation then I think the thought is that you want to escape work and be a sight see-er. You want to be a stranger in a new town and leave your troubles at home.

      If that’s one’s reason for travel though, then they definitely shouldn’t be working on the road. Honestly I don’t think they should be traveling at all and instead focusing on creating a life that they don’t want to escape from, but that’s a topic for another post.

      I do think, though that the “I’m on vacation” mindset can go hand in hand with the short term sight seeing that I reference. It’s very much the same in many respects, aside from the escape part.

      The developing world is definitely a foreign land for us. We have yet to truly challenge our comfort zone to that extent, but that’s very cool to hear that you’re finding success.

      PS. I think it’s funny that you mention drinking every night because we don’t drink, but the general message is loud and clear! 🙂

  4. jenny smythe Avatar

    hi Jeff & Marla!

    We’re in between a short and medium type of trip right now in West Palm Beach, FL. I am absolutely loving the weather and I am in no rush to head back home to the cold in Chicago. I love the look and feel of your site. Awesome work!

    1. Jeff Sarris Avatar

      That’s great! Sounds like you’re far enough south that you’ve avoided the severe weather we’re having today in Orlando. Looking forward to tomorrow when there’s no more tornado warning and clear sunny skies 🙂 How long are you spending in FL?