5 Simple Steps to Taking Your Freelance Career on the Road as a Full-time Traveler


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Getting paid what we’re worth, setting our own hours, working in our underwear: these are the icings on the freelance cake. But there’s something else that working for ourselves can provide us, something even grander than controlling our own financial fate.

Absolute mobility.

Full-time traveling is one of those big dreams many of us have tucked away in the mustier shelves of our mind, a goal perhaps attainable one day, but not yet, not now. Perhaps on some future date when we’ve accomplished this or figured out that, when we’re older, wiser, more retired…and less physically able to do it all.

I’m here to present to you the five simple steps in transitioning from your current title as Freelancer to your new one as World Traveler. Five years ago I made the transition myself, and have been living full-time on the road, with my family, ever since. It’s not as difficult as you might think. While I do like to envision myself a great web designer and pretty decent freelancer, I am in no way superior than you or anyone else in this world. The only difference is, I’ve taken the leap of faith (in myself), necessary.

First, the Great News

The hardest part about transitioning to a life on the open road is figuring out how you’ll make a living while you do so. If you’re already a freelancer, you’ve sorted that part out for yourself, and can safely move on to the Five Simple Steps… Oh, and congratulations by the way. The fact that you were brave and dedicated enough to ditch your 9 to 5 to pursue your own career path shows that you’ve got exactly what it takes to be a world class traveler and an all around wonderful individual.

Dispelling the Misconceptions

In the course of running Wand’rly Magazine, I’ve spoken with and interviewed hundreds of freelancers and entrepreneurs about how they make a living on the road. The two biggest qualms I’ve heard from those who would like to make a transition from fixed location living to absolute mobility typically have to do with their current search engine placement for their particular location and that their clients need to meet with them.

I struggled with both when I was first scheming up my four wheels on two lanes lifestyle. I can tell you now, after five years on the road, neither has been an issue.

Your Location and Search Engine Placement

Do me a quick favor, pop open a new tab in your browser and do a search for pittsburgh web designer. I’m not always the first result, but regardless of when you read this article, it’s safe to say that you’ll have seen my website by the time you hit number two. I’m not here to tell you how a one man band like myself managed to outrank even the big boy agencies in the home of the greatest football team on Earth, but suffice to say I don’t live in Pittsburgh, anymore, and I have no immediate plans to return there. The point is, I have great search engine placement in a particular city.

There is no deception at hand here. I’m a nomad, but the last place I lived was in Pittsburgh. I spent years blogging about the city, developing relationship with non-profits, businesses and individuals en masse, and donating my life to being part of my neighborhood. In short, I earned my position as a web designer there and if you’ve done the same, bravo. Nothing is preventing you from retaining that status. Just because you decide to make the world your home doesn’t mean you need to stop caring for, or blogging about or focusing your business on, your hometown.

Meeting with Clients in an Internet World

I met with clients on a regular basis during my time in Pittsburgh. I always found it to be a bit of a time waster as most of what we accomplished during our face to face meetings could have as easily been reconciled with a few emails, a phone call at most. Near the end of my tenure as a fixed locationite I began charging clients for preliminary face to face meetings, and certainly for every “Let’s get together and hash this one out” kind of excuse to get out of their office and have me buy them a coffee.

The real truth? I’ve only lost two jobs in five years specifically from not being in the physical location. One of those potential clients was gung ho about supporting truly local business (which I had to commend) and the other simply wanted someone they could call into the office to do everything from hash out design ideas to help fix their printer.

Needless to say, I’ve had hundreds of jobs and nearly as many clients over the years. None of them have received a sub-par deliverable nor have I ever sat back and thought, “Gee willikers, I’d love to get into a good, long meeting today.”

The Five Simple Steps to Transform a Freelancer into a World Traveler

Okay, I’ve gone on enough about why you should pursue your traveling desires as well as why you shouldn’t feel like it’s impossible. Without further adue, let’s proceed to the actual five steps so you can wrap this one up, get started on your game plan, and be living somewhere new tomorrow as often as you’d like.

Step 1: Organize Your Accomodations

Even travelers need a place to live. Many of us travel full-time in RVs (or a Volkswagen Bus), taking our homes with us wherever we go. This is my particularly favorite method of travel because it gives my family a sense of home, without requiring us to be stuck in one particular corner of the country.

There are more adventurous–and dare I say more illustrious–travelers who forego the whole idea of bringing their home with them. Entrepreneur Colin Wright lives in a new country every four months, renting some type of accommodation simply for the time period he’ll be there. Freelance writer Nora Dunn often has a home base for a year or so, say in Australia, and travels the larger surrounding regions. I know people who manage to stay in 5-star hotels for most of their traveling careers and others who tough it out in tents. None of them are millionaires, they just have different preferences, desires and abilities to work the system travel industry.

The best way to figure out what’s right for you is to take a few preliminary test runs. Go on a roadtrip for a week. Take a vacation to a single location. Go camping. Which of those did you enjoy the most? If it was the roadtrip, you might want to consider an RV. If it was camping…well, you get the picture.

And don’t worry, you’ll always be able to change up your style (after all, you’ll be pretty good at molding your life into what you want it to be by now). Most of us start off on whirlwind daily traveling adventures and find that we like slow travel, where you can truly experience a place from a perspective not so touristy, the most.

Step 2: Rediscover the Internet

You know the web right? It’s that place where you can stream video, download movies and albums and hop into Google Hangouts and it’s always just there, ever presently WiFi in your home.

Well you’ll need to rethink how the Internet works for you now, and what you can expect from it while traveling. While high speed access is nearly ubiquitous in the United States, finding an open WiFi network is not always that easy. Many campgrounds, most hotels, coffee shops and libraries offer free WiFi, but it’s not always reliable.

The best way to ensure that you’ll be able to stay connected for both work and play is to take the web into your own hands. There are a few options for staying connected while being a technomad.

  • Cellular Connections. You get your Internet, either by tethering your phone or using an aircard, from one of the cell providers. Verizon is the most reliable, AT&T next and really both Sprint and T-Mobile will leave you disconnected anytime you’re 30 or 40 miles away from a major metropolitan area.
  • Satellite. HughesNet is the popular one here. Your connection really only depends on your line of site to the southern sky. The more expensive method, but typically more reliable as well.

For a complete rundown on how you can set yourself up for premium success, check out this post from Technomadia that details all of the many ways you ensure you’ll never be without a connection.

Step 3: Set Yourself Up for a Digital Lifestyle

Your next task will be to transition your home office to your new mobile lifestyle. For many of us, that means downsizing from a desktop to a MacBook Pro. For still others, they take it even further and work primarily from an iPad. Maybe your external backup drive gets replaced by a robust Dropbox account. These are all of the fun little decisions and experiments that make up the months leading up to and the first few months of the transition into your new lifestyle.

Sure, ditching your dual screens for a 15″ laptop screen doesn’t sound like a dream to everyone. While you’re thinking about how that’s going to be a major lifechanger for you, though, think about waking up in a tiki hut in Bali or hiking the Grand Canyon today, the Rocky Mountains tomorrow or the fact that rent for a month in many RV parks is around $300. I think the dual screens will learn to live without us.

Even more important than understanding how your office will change though, is understanding how your work schedule will need to adapt around your travel schedule.

We all, as freelancers, need to be on top of our work. Keeping clients happy, meeting deadlines, invoicing, etc. etc. and so on. Once you give yourself the freedom to go anywhere, do anything, well, seeing the world can put a big damper on sitting in a van and typing away lines of code or doing yet another Photoshop adjustment. I highly recommend you give yourself a couple of weeks at least, if your budget can spare it, to just travel. Enjoy your new life, get settled into your new home on the road, figure out how the sewage pipe works on your RV or get lost in a new city. For me, in five years, the appeal of travel has never worn off. The initial feeling like I just had to do everything immediately upon visiting a new place, however, definitely has. So go out, take some time, revel in your new abandon. Don’t worry, though, you’ll slip into your groove and soon realize that the best way to explore new places is to do so slowly and at a pace where you can feel comfortable that you’re seeing the sites but geting your work done as well.

Step 4: Inform Existing Clients of Your New Hours and Availability

Now that you’ve seen just how traveling will affect your work schedule and availability, it’s time to discuss this with clients. Note though that many of the people I spoke with don’t ever tell their clients, or wait until it naturally comes up. There’s nothing that says you need to go out and broadcast to the world that you’re a digital nomad who is calling Alaska his home for the Summer and will be somewhere off the coast of Australia come spring.

You should, however, begin setting new expectations. If there’s a great cultural celebration going on all day why should you be sitting in front of your desk waiting for emails to come in when that same work could be done just as easily, just as well, later this evening? Be sure to make your clients aware that you’re not always going to be available at the drop of a hat, and of course try to plan in advance with people if you’ll be away from your connection for awhile, say, gone for a week hiking to the pyramids of Peru.

Step 5: See the World

Okay, you’ve made your plans for shelter, Internet access and your mobile office. You’ve figured out where you want to go and told your clients when you’ll be “back”. What else is left to do? Surely you’ve forgotten something!

Well, assuming you’ve packed your toothbrush, you’re all set! Bon voyage, happy trails and don’t drink the water!

Nathan Swartz has been a freelance web designer since 2001 and a full-time traveler since 2007. He’s been featured on FreelanceSwitch, Webmonkey and Wired Magazine. He’s currently part of a Kickstarter campaign at Wandrly.me/kickstarter and, if you’re into the nomadic freelance idea yourself, would love your support.

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5 Responses to “5 Simple Steps to Taking Your Freelance Career on the Road as a Full-time Traveler”

  • Shahzad Saeed

    You are number 3 at Google India 😉

  • Joanne Munro

    This article fills me with such inspiration and excitement I could burst! I have 2 careers, I’m a Virtual Assistant (the clue is in the name so it shouldn’t be too hard to take it on the road – in fact I’ve already worked from Vegas, France and Rome) and my other line of work is as a CV writer – which I guess I could do over Skype.

    Your article has given me the push to have a little go at being a digital nomad myself. I’m first going to try it for a couple of weeks then maybe a month at a later date. I live on the south coast of England so I can do Europe by short-hop flights or overnight train (saving on accommodation) and I’ve recently discovered the Airbnb website which means you don’t even need an RV as you can stay very cheaply in apartments all over the world.

    I’m lucky that I have no children as well so can just get up and go…

    Thank you for the push!

  • James M.

    In this day and age, especially because of the internet, this is a really plausible option for those whose feet itch for new places.

    I envy your freedom Nathan. But don’t you think things could become a little complicated when you have children who will have to go to school someday. Of course, there’s something called home schooling, but it definitely is different when kids can anchor long enough to make friends with kids their own age.

    In another lifetime perhaps, I may just try this kind of free lifestyle though. 🙂

  • Ehsan Ullah

    Great efforts made in this article Nathan. I must say that having internet connection and staying connected everywhere is important than packing your toothbrush lol.

    You’ve done a great job by placing your name on search engines with your hometown.

  • George@seekdefo.com

    In one word “great”. It simply fills my heart with hope that one can travel all over the world without being bound to a job a fixed location the monotony of daily life as is said in the alchemist “when each day is like the other day”. Living a life where every day is different seeing the sunset and sunrise of different places, meeting so many people and the ability to add all those experiences into writing. Amazing post.

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