Figuring Out How to Travel While Working

November 21, 2011

When I mentioned to an acquaintance recently that my next goal is to figure out how to travel while working, she said something like, “Well, that should be easy. You can work wherever you want.”

Which is technically true — I can work wherever I want. And I do take advantage of that, moving between my home office and a few local coffee shops and my parents’ house in upstate New York.

But traveling while working — especially when you consider the developing country-type of travel that I enjoy — is a lot different than lugging my laptop to a cafe down the street.

Right now I’m looking at taking a trip in March, possibly to East or southern Africa (but that changes according to the day, so stay tuned). Here are the two big challenges I see myself encountering when it comes to keeping my clients happy while on the road:

1. Internet access. I like to travel to places that are significantly different than my home. And in those places, fast Internet connections can be difficult to come by.

Not having a solid Internet connection can be a HUGE problem — and a massive frustration. It’s difficult to imagine when you’re sitting at home using a reliable wireless connection, but even sites that are easy to access from your couch, like Facebook, can be impossible to pull up when the signal is weak. Since my entire business revolves around having quality Internet access, I can’t just hope for the best on this. I need a solid game plan for how to maintain connectivity.

2. Working hours. If I’m going to travel, I want to actually experience the places I visit. That means not working eight hours (or longer) every day. I’d like to work half days and focus on traveling for the other half of the day. So the question is, can I get my working hours down to four per day for that month?

I’ll do some work ahead of time, putting in double hours during the weeks before the trip. But if I’m traveling for a month, I simply won’t be able to do all my work ahead of time. That’s what makes this different than a vacation.

How do I plan to attack those challenges? Here’s my to-do list if I’m going to take this March trip:

  • Streamline the biz. Here’s how:

+ Get super organized. Know exactly what I have to do each day — which newsletters and blog posts I need to write and what client work needs attention. Create a checklist I can execute each day while on the road, so I don’t overlook even a minor detail.

+ Hand over more work to my apprentices, even if only temporarily. (Lots more on outsourcing in this week’s Solopreneur Secrets newsletter, which goes out tomorrow.)

+ Say no more often. I hereby declare I will take on no new projects before March and will instead focus on becoming efficient at the work I’ve got.

+ Work ahead. Start stashing away blog posts, newsletters, tweets for clients and more. The more I do ahead of time, the less I have to do while traveling.

  • Figure out a solution to the Internet Problem. Depending on where I decide to go, could I pay for an Aircard that would connect me to the Internet wherever I am? This could be pricey, but it might also save me hours of looking for a connection.
  • Get my personal life squared away. That includes minimizing my possessions, making sure all my bills are set up to be paid online, taking care of any doctor’s and dentist’s visits I’ve been putting off. These aren’t must-haves, but they certainly make a Big Trip more manageable.

The idea of going away for a month and keeping my business running is daunting, to say the least. Because I never want my clients to feel like I’m away. It’s OK if they know I’m working remotely, of course, but if I do this right, my work and accessibility will be the same as when I’m working from my home office.

What do you think? Doable?

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    10 Replies to “Figuring Out How to Travel While Working”

    • Srinivas says:

      You’ve brought up some great points in this. Having experienced the challenges of working and traveling at the same time I can totally relate. I honestly think it’s not as easy as people make it sound for many of the reasons you brought up. One of the things that is often difficult is teaching a company how to work with you remotely when you’re in a foreign country. I was amazed that my boss who was the CEO of an internet company didn’t have a clue how to use skype. To top it off, my internet connection made it spotty. Even with a cell phone i had challenges. You realize how ridiculously long and pointless meetings can become when you’re not there in person. One thing I’ve realized is that it’s better to have a well oiled machine up and running, than it is to try to set it up from your new destination.

    • Roxanne says:

      Definitely doable, I’d say, especially if you stay very organized in the ways your post outlined. Aircards and USB internet sticks have been a huge help for me, as has having a Skype or Google voice phone number at which people can reach me as I move from country to country. Designating someone to receive mail for you in the US and scan you important documents is helpful, as is looking into co-working spaces abroad (The Hub is gaining popularity in the Middle East). Good luck, Lexi; I know that whatever you do will end up being fascinating!

    • Leslie says:

      I agree with Roxanne. It’s definitely doable, and I like the way you’re thinking about getting prepared.

      A few things that I thought of as I read your list:

      – I think this plan is easier if you stay in each place for at least a few weeks. Configuring your Internet and workspace and getting into a working/exploring rhythm can take a while in a new city and I can imagine that staying in one place longer would make it easier.

      – If I were going to work and travel, I would prefer to rent an apartment or a cabaña than stay at a hostel. At hostels I have met interesting people, but they can be loud and more interested in partying than getting things done. Also, in hostels I often find myself having the same “Where did you come from? What is your next destination?” conversations with so many people I’ll never see again. That said, I have stayed in touch with a handful of people I met while traveling, so I think it’s important to stay in at least one hostel per trip/country.

      – Think about the time when you’re getting from place to place. The other day I took an 18-hour bus ride between two cities in northern Chile. I spent about half of the time reading magazines and writing on my laptop (and when the battery ran out, my iPod. When that battery ran out I attempted to sleep.) This was possible because I was on the most luxurious bus available in this country, surrounded by mining company managers whose companies are legally responsible for them during this commute. But on a more crowded, less comfortable bus, reading and writing would not be possible. Which is fine, and probably more culturally enlightening, but it’s something to keep in mind. After a long bus or train ride I have zero desire to sit down next to a computer. It’s time to move!

      – I hope you blog about your travel adventures and take pictures of Africa (or wherever you decide to go.) 🙂

    • It’s certainly doable. I lucked out for the most part in Central America. The one long Internet outage I had was across the entire town and lasted from Friday afternoon until Monday afternoon, which I didn’t have any work planned to do. I always had a backup plan though, especially with Internet. If I planned on using Internet wherever I was, whether a cafe or the place I staying, I made sure I had scoped out at least one other nearby place in case I was on a tight deadline or had a Skype call and could relocate quickly.

    • Miss Britt says:

      I’m not even traveling in developing countries and I still struggle with both of these things traveling fulltime right here in the USA. It’s amazing how difficult it can be to get reliable Internet on a daily basis! Especially if I want to be productive with my time so that I can actually enjoy the travel.

      One of the biggest changes I’ve had to make is to train my clients to stop thinking I’m available 24/7. They have to know that I may take a full business day to email them, for example, instead of assuming they can use email like IM.

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