This series is for the increasingly large group of people who make their livings on their laptops alone, and who realize that many other “digital nomads” are cutting expenses while spending time in cities like Bangkok and Buenos Aires. Honestly, the sky’s the limit, and people who like to travel are roaming the globe paying 2nd or 3rd-World prices while making 1st-World incomes.

I’ve been doing this myself for nearly a year and a half now, almost all of that spent in Asia where US$10 hotel rooms are surprisingly nice and easy to find. I earlier discussed the great things about working while traveling, but of course there are two sides to every coin. Below are five of the “challenging” (rather than bad) things about working while traveling, and tips for overcoming many of them.

General ergonomics of hotel rooms

Those of us who already work primarily from a laptop can easily take for granted that a comfortable chair sitting in front of a proper-height desk will always be easy to find. On the road, they aren’t. Most cheaper hotels in the cheaper parts of the world (Asia, Latin America, Eastern Europe) have a reasonably comfortable bed and perhaps a table or nightstand, but none of them have a proper office chair and desk like you’ll find at the Airport Hilton (for US$150 per night).

This is an important consideration when figuring out just how much work you can expect to do. Let’s say an 8-hour day is simple enough when you have a comfortable workspace, and your alternatives are to work while lying on the bed or finding a nearby restaurant with Wi-Fi. In either of those cases you’ll find that 8 productive hours is going to be quite a challenge or impossible.

Possible solution

Plan your schedule around times when you will be in hotels like this, and make sure you add in other times when you are renting an apartment for a week up to a few months at a time. By alternating between the two you can still get a good 4-hour day in when in hotels, and make up for it with much longer days when staying in one place.

Inefficient set up for high productivity

I used to work exclusively on a 21″ iMac, which isn’t as good as dual 19″ or 21″ monitors, but still I was able to keep several windows visible at the same time. Of course I can theoretically do all my work on my 15″ Macbook Pro. It’s just that it tends to go slower and be more maddening when I’m constantly having to open and close windows all day long. Don’t underestimate the added efficiency of extra screen real estate, at least for multi-window projects.

This situation definitely adds an hour or two to my average day, and there are a few other things that can also be challenges. Most of us have quick access to a printer of some kind at home, but printers in hotels are rare and/or expensive.

Possible solution

Fortunately, prices on external monitors are very low these days, even in most smaller cities. You can now find a 20″ monitor for around US$120, or perhaps a bit more in Europe where taxes are higher. Using the strategy above of stopping in some places for weeks or months at a time, it’s worth buying an external monitor when you arrive. You might find a used one or be able to easily sell yours used when you leave, but even if you just give the thing away then the US$120 is money well spent for the added productivity.

Language barriers locally for some specific things

When you are living in your home country you’re obviously used to communicating with everyone you see, in full detail. However, when you are traveling through Thailand or Turkey, for example, you are far more likely to come across people who know only enough English to check you into your hotel or sell you a beer. When I was in Kochi, India, asking about Mac laptop repair, it took hours just to find someone with even the vaguest idea of what I was talking about. (And by the way, I obviously started on Google, but most local business results will be in the local language.)

That’s just one example, but plenty of others will come up eventually. When you are on a vacation you’ll just figure that you can take care of these things when you get home, but when “home” is the road you’ll need answers.

Possible solution

Sticking to larger cities usually minimizes this problem, at least to the degree that finding someone who speaks fluent English is usually doable. In smaller towns it’s typical that people will try to be polite (and never say no) pretending to understand the question. It’s often best to assume that they don’t understand, and just keep looking for a proper English speaker instead.

Ever changing social scene

Not so much from a business standpoint, more from a living standpoint, long-term life on the road will get lonely. It’s a different kind of lonely though. In most places that you’ll go there tends to be hostels and expats and others that are always ready to join you for a beer or two, and actually the non-stop party thing can also be a problem. The challenge here is that when you move on to your next stop it’s likely that you’ll never see or hear from those people again, regardless of your parting declarations to the contrary.

Possible solution

Actually, Facebook itself has elminated part of the problem in recent years. It’s always easy to see what all your friends are doing and thinking about every hour of the day. For more meaningful contact it’s also now quite easy to make free (even video) phone calls from any two points in the world using Skype.

We recently talked about the best ways to communicate while on the road, and this all goes for personal communication as well. If you set up weekly or bi-weekly Skype calls with some family and close friends then it’s unlikely you’ll feel too isolated on the road. And you’ll always have your new drinking buddies down at the bar too.

Lack of connection and inspiration

The reason that tech startups continue moving to San Francisco or Silicon Valley or Austin or New York City isn’t because they have faster internet or cheaper office space (except for maybe Austin). It’s because those areas are inspiring and ultimately very helpful in pushing your idea or business forward.

When traveling around you’ll be inspired by plenty of things yourself, but unless your primary field is travel itself (as mine is) then you’ll probably feel quite cut off from your industry. You’ll hear stories of great products or ideas that friends are creating back home, yet it won’t motivate you to push yourself in the same way.

Possible solution

In addition to the thing just above about setting up regular Skype calls with friends or others in your industry, it’s getting much easier to stay connected through things like niche podcasts and Youtube shows than it was only recently. Online forums are still going strong for many topics, and now there are Facebook Groups, so while it may not be an ideal replacement, those who put in the effort can make it work.