How to Keep Your Freelancing on Track While on the Road

If you’re like me, you don’t want to separate work and travel. As a freelancer, you don’t really have to either. As long as you can find an Internet connection, you can get your work done.

Recently, I took a trip and was also able to get some work done from my tablet. While the trip wasn’t a permanent switch to a location independent life, I learned quite a lot. In this post, I’ll share what I learned about working “on the road.”

Planning is Essential

The most important part of traveling and doing freelance work is the planning. Proper planning will help you to ensure that you have everything you need to get your work done. Here are some planning steps that I took:

  • Be sure to bring the right equipment. For taking short trips with a relaxed workload, bringing a tablet may work fine. For longer trips, you may wish to bring more of a workhorse such as a netbook or even a laptop computer.
  • Learn where the WiFi hotspots are. Knowing where to stop to find an Internet connection can be a huge timesaver. Deb Ng’s Kommein blog has a great list of places that offer free WiFi.
  • Notify key clients. If you’ll be unavailable for an extended period of time (such as when you are driving or flying), you can notify key clients of your travel plans. You may wish to give them an alternate way to contact you.
  • Make sure that you can access your workfiles. Tools like Dropbox and Google Docs allow you to access files online from nearly anywhere.
  • Don’t expect to work full-time during a vacation. If your trip is intended to be a vacation, for goodness sake, take at least some time off and relax. Getting the opportunity to relax is important for keeping your creativity fresh.
  • Discuss working with those who will travel with you. This is particularly important if you are traveling or visiting folks who don’t really know much about freelancing. Explain when you’ll be working and when you’ll be visiting.

Once you’ve done a little planning, you’re almost ready to travel. However, there are some additional factors that you should be aware of.

Beware of the Following

If you are a traveling freelancer, you do need to be careful. Be aware that, even with the best plans, things may not go exactly as you intended. Here are some obstacles that you may face:

  • Internet “hot” spots that aren’t so hot. Just because a place is supposed to have wireless Internet available, doesn’t mean it will be available when you get there. The connection may be down or they may have even discontinued the service.
  • Scope creep may ruin your vacation. If you schedule your time too tightly and your project requires more work than you realized, you may find yourself tied to your computer while everyone else is having fun.
  • Security problems. Not all public WiFi access is equally secure. There are also applications that unscrupulous people can use to spy on your activities and even to steal your personal information. Be sure your system has proper security precautions.
  • Some places are still unconnected. A few years ago, I visited Yellowstone National Park (which is absolutely beautiful, by the way). At the time, I discovered that there are many places in the park where you just can’t get a cell phone signal.

Naturally, you should never ever try to drive and access your computer equipment at the same time. Likewise, don’t leave your computer equipment unattended–even for a few minutes.

Also, don’t log into a secure site on a public computer and leave the site open. You don’t want to take the risk that someone else can access your information. Even a social media site like Facebook should be closed as soon as you are done using it.

Other Thoughts on Traveling and Working

Since the main purpose of my recent trip was other than working, I did scale my workload back. Working while traveling on this occasion was a convenience, not a permanent lifestyle change (yet) for me. Having a lighter load definitely took a lot of the pressure off of me.

I was pleasantly surprised at the number of connectivity options that a traveling freelancer now has available. Working in public spaces is becoming increasingly common. So, you don’t need to worry about lugging your tablet or laptop into a restaurant, hotel lounge, or other public space. Chances are, you won’t be the only one.

Likewise, hotels and other facilities are becoming used to hearing the question, “do you offer an Internet connection?” If you aren’t sure if there is a connection where you are going, don’t be afraid to ask.

Your Thoughts

It’s a great time to be freelancing! The expansion of Internet connectivity means that most freelancers will have many choices about where they perform work tasks. For some, this will mean fully embracing a location independent lifestyle. For others, it will mean that taking a trip no longer means taking a break from freelancing.

What tips can you add for combining traveling and working?

Image by Nicholas_T


  1. says

    Excellent points. I keep a Verizon MiFi on me virtually every time I leave the house, so I’m not subject to the whims of a particular hotspot. Granted, I’ll hop on wifi when I’m able (increased speed and no data costs), but I use the portable hotspot quite a bit.

    Beyond that, I’ve built my personal system to be easily accessible from any computer. As with you, Dropbox is a big part of that. All of my files are in there (~30GB), and I’ve shifted most of my software to “portable” versions that are stored in Dropbox so that the settings travel with me. This is particularly great for programs like FileZilla where I’m always adding new client FTP info to it — every computer stays in sync!

    Throughout the day, I move around between my desktop, laptop and notebook (plus Xoom and phone), and every one of them have every bit of data I might need. Other tools that help with this are things like Gmail, Google Docs, Evernote and Nozbe.

  2. says

    Great tips Mickey! It sounds like you’re set up to be as mobile as possible.

    I wonder if your MiFi would have worked in Yellowstone National Park.

    Sharon, Great minds think alike. I look forward to reading your post.

  3. Scott Rose says

    This article has some wonderful advice, but you skipped over the biggest piece of advice of all: telling all of us that you used an iPad to get all of this done. Not thrilled with you generically calling your iPad a “tablet”, especially considering that the key reason you could get work done on the road is the sheer number of apps for the iPad, the amazing versatility of the iPad, and the rock solid reliability and everlasting battery of the iPad. There aren’t any other copycat tablets that even come close to functioning as well as the iPad, and there are certainly none that I would ever take on the road with me besides the iPad.

  4. says

    Laura — It needs a Verizon signal, so it probably would have had quite a bit of downtime. :)

    Scott — I don’t think it’s that simple. While I agree the iPad is the best choice for most people (75%?), it’s certainly not the best choice for all.

    The top app that most people use on a tablet is email. If you use Gmail or Google Apps, the experience is far better on a Xoom and you can get a lot more done. Granted, if you don’t use a Google-based mail system, the default email app on iPad is better than the default Xoom email app.

    Same for the browser, with desktop-like tabs, syncs to Chrome, and Flash that can be toggled on if you find a site that is silly enough to still require it. The iPad browser is certainly solid, but the Xoom browser bests it in virtually every way.

    Beyond that, the apps almost all flow in favor of the iPad, hence the recommendation that most should get one. However, since I’m a Gmail user, I can get a whole lot more done on a Xoom than I could on an iPad, and there are 200 million more people that would experience the same thing.

  5. says

    Hi Scott,

    Well, if you’ve read the earlier post about my iPad (see the link above), you’d see that I was soundly criticized for not being inclusive of the other tablets–hence the generic use here. I have to say, I haven’t used another tablet so I don’t know how many apps are out there for other devices, although I understand there are quite a few for the android platform.

    Mickey–Yeah, I’ll still think there are places where you just can’t get connectivity. At least for now. :)

  6. says

    really enjoyed Mickey comments then the post itself…Mickey can u tell me how u manage the settings and files all in sync…i wud really love learn that art…coz i try to switch on desktop, netbook, laptop and iphone and desperately want theme in sync

  7. says

    Ensemble, I agree that comments are what makes a post really valuable. I’m always disappointed when we publish a post and no one in the community steps up and says anything. It’s the shared knowledge that makes us strong…

  8. says

    Laura, these are good points you make. In fact, as I write this I am working at Hope Cafe Raleigh, a Christian “hot spot” where the connection is excellent, the food is good and where the fellowship is a blessing. Even though I’m in a public area, I’m managing to get my work done without much distraction.

    I think it is important for writers to have options open to them. The big drawback are those “not so hot” spots where the connections are weak. There is a Panera Bread near to my home and it offers a solid connection, but the environment is too noisy to suit my tastes.

  9. says

    A friend and I started a small programming shop a few months ago. With that, came the goal that we would be able to work from wherever, whenever. This goal came about after a 5-6 month stint in South America to unwind after leaving my last position.

    Since January 1st, I’ve been driving around the United States seeing some wonderfully things and meeting great people. You could think of me as the eternal “on the road” programmer.

    One of the things I’ve found most useful is a good set of in ear headphones. You can play anything from white noise to loud dance music, but when you need the ability to block out the noise in a coffee shop so you can plow through a task, nothing beats. them.

    Also, if you’re going to be on the road for any extended period of time… please please please backup. Bring a separate hard drive AND use an online service. **Which you should be doing anyway, but it’s extra important on the road.

  10. says

    Great tips for any creative professional while on the road!

    I’m always quite surprised when some limit their own ability to travel and work. For me it’s usually a situation of getting up early for a scheduled couple hours of attnetion to projects or writing – and then I can join my travel companions in playing tourist, or perfecting the art of doing nothing at all.

    My design and writing business has been totally portable for over a decade now, in part due to one year of traveling and living in hotels for over 25% of that period of time. In the last couple of years I have worked from an incredible farmhouse outside of Lucca, Italy (which had better WiFi than I have at home), two stays at a beachfront compound on the island of St. Croix (a neighbor’s hilltop home served as the WiFi “internet cafe” and you could get a decent cell phone signal by standing next to a particular palm tree in the yard) and a week-long teaching gig at a design/innovation college in Monterrey, Mexico. In addition, during that time, I’ve worked from a bed and breakfast inns and hotels in Denver (twice); Bismarck, ND; Boise, ID; Austin, TX; Seattle, WA; Boston, MA (twice); Yakima, WA; San Diego, CA; Kona, HI; San Francisco, CA; Chicago, IL; and numerous locations around the state of Oregon.

    It has been helpful for me to have a small plastic storage container of office supplies packed to go at a moments notice. Post-It notes, paperclips, pens, notepads, blank cards, envelopes, postage stamps and more are in the box. I also have any cables, converters and connectors I may need while traveling. Often I will even travel with a small portable color printer.

    I don’t necessarily work too much when traveling. However, it is always good to have a connection to the business world via email or the Internet. Once, while staying in a Seattle hotel for a week, I received an email from Fortune magazine that needed a nearly immediate response – which led to me being featured in an article in the publication. Without my “portable office” laptop I would have missed out on an incredible opportunity.

  11. says

    It would seem to many that you should have an adjective associated with the word Freelance to know what you’re talking about. Think about it. how many “different” jobs are there being done by freelancers?

  12. says

    I’m a long-time freelancer, and have traveled a lot already this year. This post has great tips. I have two thoughts: I really, really enjoyed my actual vacations. I prepared everyone and everything well ahead of time and loved being unplugged. That said, during my next conference or working vacation, I must get an iPad with a Bluetooth keyboard (I need the old-school key clicks). I cannot lug this heavy PC on my back anywhere ever again.

  13. says

    There’s some great information in the comments here!

    Matt–noise could definitely be a factor. Especially if you are doing something that requires a great deal of concentration. That’s something to consider when you are choosing a remote spot to work from. I notice that Taylor Smith recommends noise blocking headphones–that might be something worth checking into.

    Taylor, Thanks for sharing your experiences as a mobile freelancer. I agree that backups are crucial.

    Jeff Fisher, Wow! What can I say. It sounds like you’re living the dream that I would one day like to experience with all that travel. :) Because I have school age kids my freelancing on the road is limited to, at most, about a month each year during school breaks.

  14. says

    Hi Laura! Great article – thanks for sharing some good insights. My boyfriend and I are both freelancers and we took two road trips last year for the holidays … I had a great set up with a lap desk, my awesome Inspiron Duo laptop/tablet, our Sprint overdrive (hotspot), and Dropbox – we were all set and were able to have a great balance between work and play. Certainly one of the better parts of working for yourself!

    ~carpe diem~

  15. says

    I hate working on a laptop, because it makes me slouch. I had to travel recently, and so bought a 3G modem, but I misunderstood the contract (I’m in Brazil) which was limited to 6 GB of data transfer. Of course, I didn’t think of that when I installed dropbox on the laptop and it downloaded all my files (9Gb), so after 2 days I had reached my limit!

  16. says

    Paul — That’s a good point to remember! I typically try to get my devices synced up at home (Dropbox, Evernote, software updates) before I take them on the road so I can avoid that issue. With about 30 GB in Dropbox, it could be a big problem. :)

  17. says

    Mickey – what I love about Dropbox is that each time I share a folder, I get rewarded with more storage space … I’m up to 53.5 GB now :) But totally agree that it is a great habit to get everything synced up before you leave.

    Paul – I realized I’m slouching now, sitting at my desktop! Thanks for the reminder – my Grandmother would be proud right now …

    Happy weekend!

  18. says

    Yet another article in the style of “If it’s going to rain, please make sure you buy an umbrella. I hope this is useful for you.”.

    As I said in another post, FreelanceFolder is becoming a collection of extremely-easy-to-write articles that provide no real value other than a lot of keywords.

    I like Freelance Folder. We really need this site. But it needs to go back to quality content. Really.

  19. says

    Thanks for all the comments everyone. Apparently there is quite a bit of interest in traveling and working on the road. I especially appreciate the tips.

    Juan, I’m sorry you didn’t find the article useful. Judging from the comments, however, there were many readers who did get something from the article. Keep in mind that as a member of the community you’re always able to suggest post topics that would be of interest to you or even submit a guest post.

  20. says

    If you are not using webmail (yes, some prefer a “real” email app) make sure that you have an email provider that let you send email through their SMTP server, regardless of which network you’re in.

    This is usually done with authenticating with username and password when sending, but not all providers offer it.

  21. says

    Hi Laura,

    After three years of continuous freelance work, I got the time last week to unplug and take a three-day vacation – for real. I’m glad my clients understood and of course, I left no pending works for anyone to worry about. I love your tips here and even if I’m not really for mixing business with pleasure, I’d say having a plan is better than none. I’m just concerned about public WiFi with all those hacks like last year’s FireSheep… I guess, I’ll have to be very cautious…

  22. says

    Hello Laura,

    Thanks for the good summary. Working on the road a lot, I know how important it is to be well prepared before you leave. I belive however that if you backup properly and do not go to places that are to far remote everything should be fine.

    Can’t wait for my trip to Thailand next week for another beach working vacation ;-)…


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