Taking Your Business on the Road: How to Work While Traveling

One of my favorite things about being a freelancer is the flexibility it brings. Having control of who you work for and when is one of the boundless joys of freelancing. Couple that flexibility with location independence, and it opens up all the possibilities that come with taking your business on the road.

But traveling while working is not all beer and skittles, it takes real planning and the willingness to roll with the unexpected. Knowing how to travel and work can mean the difference between enjoying your trip or needing a vacation from your vacation.

Fail to Prepare, Prepare to Fail

When your goal is to work while traveling you have to think about more than if you brought enough underwear. While you will never be able to prepare for every eventuality, there are plenty of things you can do to avoid some of the traveling pitfalls.

• Schedule a slow work load. You may think you can handle your full work schedule while being away from the office, but let me tell you – you can’t. It’s no fun worrying about deadlines while you’re worrying about trying to catch your next train. So work hard before your trip so you don’t have to work hard on your trip.
• Prep your clients. If you have clients that will have to be in touch with you while you are traveling, let them know that you will be on the move but assure them that you will be taking their work with you. Inform them if you are going to be in a different time zone and replying to their emails at odd hours. You may not have mobile phone access, so let them know that email will be the number one way to get in touch.
• Prep your laptop. If you use a laptop as your main computer, you’re already in a great position to travel as you work. If your are like me and work from a desktop, you’ll want to make sure your laptop has everything you need on it. Sync your email, transfer all the files you think you’ll need (and even a lot of those you don’t), toss any critical files into Dropbox, and make sure you have all the software you are going to use installed and ready to go. As a added bonus, drop your bookmarks into Dropbox or use an online bookmark service. There’s nothing more annoying than hunting for a website you know you have bookmarked on your office computer.
• Travel light. Find yourself a comfortable backpack that can hold all your gear. But before you stuff it full, prioritize your essentials. Do you really need to lug around your DSLR and a 10 pound zoom lens when a quality compact will do? I’ve spent too much time kicking the crap out of an overloaded backpack to want to hump around equipment I end up not using.
• Prepare for the unexpected. I don’t know why it is, but traveling seems to bring all my clients out of the woodworks. No sooner have a left the door than clients I haven’t heard from in almost a year are emailing to talk about their project. Don’t get me wrong, it’s a great problem to have, but be prepared to handle some work you may not have planned on. Transfer even old or delayed projects to your laptop and be prepared to have the FTP login information accessible for all your clients. I like to have a service like KeyPass set up with all my important security information and the encrypted file available on Dropbox if I need it.

Wireless – the Fickle Mistress

In a perfect world you will have fast and reliable internet access for your entire trip. But as I sit here working on this article while taking a train across Canada, I notice my promised wireless access is currently experiencing trouble. What I planned to be six hours of online work has suddenly changed to either offline work or six hours of twiddling my thumbs.

• Plan your online and offline work. There’s plenty of wireless internet out there but always have a backup plan when connections don’t go your way. You may want to research the area and the means of travel you are using to make sure there’s internet readily available.
• Have planned work stops. Plan to devote certain days or parts of days to getting work done. Do your research so that you know you’ll have all the tools and access available to do your job. So even if all your wireless plans fall through, you still be able to get at least some work done.
• Scout ahead before you commit. I always look for an AC plugin and wireless access before I buy my Americano. You may think that every Starbucks is freelancer friendly, but that is not always the case. Scout your planned work area before you commit yourself to buying anything.

Other Traveling Tips

It seems like you always learn something new when you travel. Here’s a few tips that I’ve often found out the hard way.

• Charge your gear at every opportunity. I have two rules when traveling – never pass by an opportunity to go to the bathroom and always charge your electronics when you have a chance. Mobile phones and laptops will always die when you need them the most.
• Prepare yourself mentally to face problems. Nothing will ever go perfectly according to plan. How you respond when things go south is completely up to you. Keep your cool and think things through rather than do what I sometimes do and throw what my wife refers to as my ”daily rant.” I like to pretend that I’m on the Amazing Race and this is just another challenge to overcome.
• Don’t work too hard. Remember you are out there to enjoy life and your surroundings. If you wanted to spend your whole day with your head stuck in a laptop then you could have just stayed home. Plan your work, but also plan to enjoy your travels.

Do you have tried and true travel tips or want to share your stories about taking your work on the road? Let us know in your comments!