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How to Make a Living on the Road

travel-work

From Columbus to Lewis & Clark to Kerouac, every great traveler has had at least one thing in common: an entrepreneurial spirit.

A new generation of mobile individuals has risen, the revolution is over, and for the rest of America, that means fulfilling a lifestyle where every new day is to be spent at your leisure is a real possibility. We spoke with a dozen full-time travelers, from self-proclaimed nomadic geeks building iPhone apps to blue collar migrant construction workers ready and willing to work. Liberal college students to a Christian family of 14, some were barely of the legal drinking age while others are nearing a traditional retirement, but already seven years into their new “vacation lifestyle”. That term should not be taken lightly, though, because more than any other common thread, these wandering workers share one thing in common: they are ready and willing to create their own work.


The Internet is in need of a Noah in this particular arena, there is a worldwide flood of information on how to live and work from the road, however much of it has been procured by travel writers who are not also full-timers, while other very insightful articles tend to only apply to their particular author’s experience. Here we attempt to provide a solid, systematic outline of exactly what steps nearly everyone we spoke with followed. There will be bullet points, there will be diagrams, but we’ll be sure to throw in some real life tales as well. Grab a coffee, kick back, and have the atlas ready, as we’re fairly certain that by the time you’ve gleaned every last syllable available here, you’ll be itching to start picking out the spots on the map you want to head to first.


Prelude to a Lack of Fear

Graph of full-time travelers' incomes: 50% made less than $30k, 35% made $30-50k, 10% made $75-100k, and 5% made $100k

Our goal is to provide concrete examples of how to prepare for living on the road, and then actually making the transition. We’ll show you figures, give you ideas for actual income sources, and debunk some often shared rumors. What we can’t do though is give you the nerve to follow through with your own particular plan. Committing to realizing a dream is an unattainable act for many of us because of the very nature of dreams: they are easier to sleep through than to write down when you wake up. We have a little good news though: in our own experience, and with nearly everyone we spoke with, where the largest fear was not “how can I make a living while traveling” as much as it was “what will my friends and family think”, the response was nearly universal support from their friends and family when they finally let the cat out of the suitcase.


Step 1. Get Over It

We have a tendency to think that though others are capable of accomplishments, for us it just wouldn’t work. “If only I were young again,” “Well I have three kids,” and “I need to rely on a steady paycheck” are some of the most common walls we build up around our amazing human brains. We as humans—armed with the same grey matter that tamed wild horses, built ships to cross the Atlantic and shuttles to the moon—have yet to find a limitation to what our imaginations can, when combined with able and willing bodies, accomplish. Indeed, the only rival to the freedoms we can create with our minds are those very walls we build up around them in desperation for a sense of comfort. But comfort can change, and as much as your home and 9 to 5 income provide you with a sense of security now, the feeling of being responsible for your own fate, of being flexible with your monthly bills, and of the waking up to the snow capped peaks of the Rocky Mountains as your own personal real life painting through a window…well, you will find comfort in this if it’s truly your passion to pursue.


This lifestyle is not just for hippies. It’s not exclusive to vagabonds, and you don’t suddenly become a hobo because you no longer have a home with a fixed location—though the term hobos actually does literally mean “traveling worker”. You instead follow in a centuries old tradition of traveling while finding work, which when combined with our modern technology, opens those doors up to more than just bards, migrant farmers and Italian explorers.

Today, some full-timers call RVs there home while others find hostels, couchsurfing opportunities or even rent apartments for a few months at a time. After a while, most learn to appreciate slow travel, where you take all the time you need in a location to both experience it more like a local than a tourist and make plenty of time for work, too.


“If only I were young again.”

Who's Traveling? A graph showing 23% travel solo, 26% do so as two or more adults at a time, while 49% of full-timers are families with children

“We had always wanted to take an extended road trip, but just never knew how to get started.” René Agredano and Jim Nelson began their traveling lifestyle—as they call it, Live. Work. Dream.—in their late 30′s. Long gone were the days when perhaps they could have thrown on a couple of backpacks and hiked around the West Coast before beginning their careers; the two had already established a successful printing business in Humboldt County, California. They had plenty of friends, family, community. Like so many of us though, they were constantly holding onto a little fire inside of their bellies, one that wanted to come rushing out of those homely human hearths and spread wildfire across the country.

“What ifs?” made themselves more heard than “why nots?”, and as René puts it, “Taking time off just seemed impossible. Before we knew it, ten years had gone by and were in our late 30s, wondering ‘What happened?’”


Of course, being in your late 30s is far from being old, but it’s not exactly in the spectrum of “plenty of time to start over”, either. Anyone who’s ever blown out 30 candles in one go knows that there is a sense of aging that comes with the date, even while our venerable elders make us clear and aware of just how very young we are. Jim and René could have continued bringing in a weekly paycheck from their own profitable printing shop. They could’ve waited another 25 years and probably would have had enough money by that time to retire into an RV and begin traveling around the country, seeing the places they’d always wanted to see, doing some of the things they’d always wanted to do, but at 65, well, the saying “If only I were young again,” begins to start ringing a little more true.

For them, a catastrophic event amplified the magnitude of that too oft ignored axiom, “Life is short.” Their German Shepherd, Jerry, was diagnosed with canine osteosarcoma, terminal bone cancer.

a dog missing one leg is soaking wet with a stick in his mouth, presumably produced from the lake in the background
Jerry: René and Jim's inspiration to hit the road.

“When doctors told us he had just months to live,” René doesn’t seem morose when she tells of the situation, rather the opposite, grateful for the quality of time it did provide them, “and the only way to give him a good quality of life during that time, was to amputate his leg, we were stunned. Suddenly, working so hard just for more money didn’t seem like it was worth the stress if it meant that we wouldn’t get to spend the last few precious months with Jerry.” It took them seven to get on the road, and though Jerry had only been given four months to live initially, they spent the next year and a half with him as copilot. The two began a website, a kind of online support group, for other humans who’s dogs have lost a leg.

“I never realized how the death of an animal companion could bring a person to their knees with pure grief,” René wrote on her blog one year after Jerry passed. To think the very same dog was also the driving force behind this couple’s migratory lifestyle—five years later, they’re still exploring the country, living in their 24′ Fifth Wheel and making a living from the road, with no plans to stop anytime soon—is a nudge in the right direction to anyone looking at the difficulties their own particular situation might pose on pursuing the rolling hills and winding highways lifestyle. The only thing certain about the future is that you have the ability to manipulate your own.


Jim Nelson and René Agredano sitting on the red rocks of Utah's National Parks.
Jim and René of Live.Work.Dream

“But I have kids.”

Congratulations! For families traveling with children, there is no doubt about it that the experience is very different from those folks who travel solo or with adults only. Of course, the exact same thing is true of your life at 555 Fixed Address, Yourtown, America. The moment you first decided—or for many of us, made the “miraculous mistake” of—having babies, your life changed forever. The path you follow with those little ones, however, did not. It’s still as open as ever, and all you’ve got to do is walk it. The more little feet pattering behind you, the better.

a chart showing 66% of full-time traveling families have 1-2 kids while 34% have 3 or more children living with them


Meet Dana Ticknor, who along with her husband Vaughn, travel full-time in their 40′ toy hauler, with their 10 kids! “10 of our 12 children,” she would correct me. “Our oldest two children are grown, and have their own places.”

The Ticknor Tribe, as they refer to themselves, range from seven months to eighteen years old. They’ll have been on the road for three years in July.

“To be honest,” Dana tells me from an RV Park in Montana, where they’re currently serving as campground hosts, “we never even gave fulltiming a thought. If someone would have told us 3 years ago that we would be living in our RV with our (at the time) 11 kids, and traveling the country, we would have thought they were crazy.”

The impressively large family had sold their home to buy another, first searching for the right land where Vaughn, a builder by trade, could create their masterpiece home in Montana’s backcountry.


9 children pose for a picture with their mother, holding their youngest sibling in her arms
Jacob, Molly, Eli, Savanna, Bethany, Dana with Caleb, Thomas, Daniel, Joel and Emma of the Ticknor Tribe.

“We didn’t find the land that we wanted right away,” she says, “and winter was quickly approaching. We had learned 10 years earlier that landlords don’t rent to families with many kids, so this time we didn’t even try—we decided to pack our kids into our 15 passenger van, toss a few clothes into our 30′ bunkhouse travel trailer, and take an all-winter vacation. Two weeks after we left town, we had a family pow-wow and the decision to postpone a house, indefinitely, was unanimous. We’ve been gypsies ever since.”

a chart showing the number of hours full-time travelers work on average, 27% work less than 10, 53% work 10-35, while 20% work 36 or more.


“I need to rely on a steady paycheck.”

There is a great misconception about being employed. Think for a moment about a dam. It seems quite important; a massive wall meant to retain water which then becomes a lake. Rich people find the lake beautiful, and so purchase homes on its banks and float boats through its waters. A town grows down river where people in the service industry can live more affordably, making a living selling beers and shrimp cocktails to the rich folks who live back up at the lake, the very same which now provides the townspeople with water. At first, it would seem that everyone and thing is living in harmony: the lake needs the dam to keep it from just being a river, and the rich need the lake because it provides them with their much required recreation. The rich also need the townspeople to provide the services they require to pursue said recreation, who in turn need them to make a living here by the lake the dam built. At first glance, it even seems like the dam is the most important player in the whole game. Remove the dam, goodbye lake, and simultaneously, goodbye reason for the rich to live here and the town goes underwater.


With this thought process, the dam should feel pretty secure about its position in life. It is literally the wall holding up the entire ecosystem. The only problem is, if the dam proves too troublesome or expensive, or if it just gets old beyond repair, well, a dam is replaceable. More so, the rich can always choose to just find a new manmade lake to call their home, this time with updated lighting fixtures and gates to keep the townspeople away. Like the bartenders, mechanics and limo drivers in town, the dam and everything below the highest point in town—the hill where the rich folks lived—is interchangeable with other, similar parts. The dam will only remain for as long as the cost to maintain it doesn’t exceed the desire to own it, as has been proven by millions of Made in China stickers and Indian telemarketers interrupting us at the dinner hour. No one will be looking at the dam for all of its beauty and history.

As an employee, you are the dam. Cheaper labor overseas, robotic factory lines, smarter bits of software and a bad hair day for your boss are but a few of the multitude of reasons why your paycheck is anything but secure. When you become your own source of income though, when you as a human become an entrepreneurial enterprise all unto yourself, then you are no longer at the mercy of your employer. Only the employed can be laid off or fired. As the maker of your own means, you have ultimate control over what you do, how you do it, and how much money, within reason, you can make while doing it. There is no unemployment, there is just work harder when it’s necessary, take it easy when times are fat. Build dams, don’t be one.


“When you live from an attitude of abundance, instead of scarcity, it’s amazing to realize just how many opportunities are out there if you’re open to them.” The words are those of Cherie Ve Ard, a software engineer and willing-to-try-anything adventurer who travels with Chris Dunphy in a vintage 1961 35′ GM bus conversion.

Cherie, who also manages and designs software for a family business, as well as being part of the couple’s joint venture Two Steps Beyond, expands on the idea. “Living on the road gives you tremendously more agility to choose your income levels and expenses. Don’t have work coming in this month? Unlike having a mortgage or rent payment that you must make, you can choose to stay still and find a cheap camping opportunity, house-sitting, workamping or other opportunities.”


Two massive flat panel monitors are secured to a desk in their impressive “old-school” bus via a custom fabricated device that Chris designed. Their mobile office and home on the road is reminiscent of Neo from the Matrix’s room: a little tight, improvised and full of modified tech which allows them to stay nearly ever-connected to the very Internet which they typically get their lifeblood from. On a particular day in Austin when I stopped by their spot at the Pecan Grove RV Park, as some friends began to wander in from the Texas sun and I squeezed back out to make room for them all, I found myself particularly jealous of their particular find. At $8000, their home is classier than anything our prefab generation could affix to some suburb in Cincinnati, cooler than any teenagers room Hollywood has managed to dream up yet and the lack of a 30-year mortgage—the couple bought the rig outright—allows them to pump your typical homeowner’s worth of interest rates into their diesel tank.

“I don’t feel particularly different,” Chris continues. “I’ve seen enough layoffs to know that traditional jobs are never as secure as they appear, and there is a lot of freedom that comes from being able to control your expenses and even locale.”


a couple sits outside of a silver and blue-striped vintage bus at an RV park in the woods
Cherie Ve Ard and Chris Dunphy of Technomadia.

Step 2. Preplan, A Little

It’s rare that you hear advice touting the benefits of doing less planning, less research. This is one of those cases.

When I was a young boy, growing up on a farm in rural Pennsylvania with a few of my cousins who lived a few acres over, we were hardy little kids accustomed to climbing to the tippy tops of trees, walking across ice covered ponds and the idea of wearing a helmet while riding your bicycle was as foreign as the concept of traffic. One of our favorite pursuits was jumping. We jumped our bikes off of ramps, catapulted our bodies over electric fences, and 5rddove from cliff sides into lakes. Even more frequently though, we would sit at the edge of some new high precipice, the door of a hayloft, a second story porch, the roof of a shed. We understood that we had limits, and we were keen to test them. If your feet didn’t sting when you landed, it was too low a distance to be proud of. If your knees hurt afterward, that’s about as high as you needed to go. The lesson learned above all others though was that fear has a way of fermenting in your mind, the longer you sit and think something over, the more likely you are to allow all of the things that could go wrong—though in my experience jumping out of trees and off of buildings they never actually did—pile up in the back of your head until you’re paralyzed by your worst enemy, your own imagination in fear mode.


That’ll just leave you climbing back down a ladder while the rest of your friends are half a mile down the road on their bikes, off to some next great adventure that you’ve already proven yourself, at least for the day, unworthy of participation.

Humans have been making a living through travel well before our modern WiFi cellular digital century. It is not a radical new concept, given the grand scheme of the history of man, the fact that so many of us live such stationary lives is actually a new idea. As recently as the 1920s, it was common for everyone from traveling salesmen to carnival workers to migrant farmers to drift through, do a little work, and then be on their way. Passers through, drifters, foreigners. These are the types of people living lives we want to write books about, we go to watch play their lives out in the movies. Aside from the occasional few depressing flicks where Leo Dicaprio or Ryan Gosling show us just how depressing getting old with their wives and watching their dreams turn into mortgage payments, no one goes to the movies to watch people live in the suburbs.


My goal here isn’t to bash stick-dwellers though, but rather to show anyone who might be interested in the alternative American dream of living and working from the road just how very possible it is. There are actually two steps to preplanning: thinking about making your lifestyle desires a reality, and then actually working towards making them happen.

It’s that first part, the thinking it over, wondering how it’ll work, reading about other people on the Internet who are doing it, that’s the bit you want to skim over as quickly as possible. If you’ve read this far, chances are you’re already committed to the idea, you already really want it, and you just need to move on to the actual process. One could argue that there are a bunch of additional steps involved now, where you sell all of your stuff, your house, cancel your cable bill, etc. but those are outside of the realm of this particular exploration. We’re focusing on how to specifically make a living while traveling, so let’s get back to doing just that.


Step 3: Take Control of Your Finances

Chris Dunphy, still in Austin a few weeks longer than originally “planned”, was in an ideal situation when he ditched his Prius for a Jeep and a 16′ T@b Clamshell trailer.

“Fortunately, I was debt free, had a nice severance package, and ample savings accumulated–so I was able to concentrate on getting on the road, trusting that I’d be able to figure out the ‘generate an income’ thing later.” Like his now fellow traveler Cherie, he had lived a life largely free of amassed debt through a combination of personal philosophy and decent salaries working in the mobile industry in the early 2000s, when iPods were still an exciting new idea, and the notion that a cell phone might someday have an operating system, not just a contacts list and a send button, wasn’t much more than a seed slowly growing in some future Steve Jobs enviers. This combination of hard work and the all too rare these days wherewithal to remove themselves from the ever growing trend of spending more than you earn set them both up perfectly for their individual departure dates. “I’ve been on the road now since April 1st, 2006,” he continues, “with no end in sight.”


Consolidating debt into a big fat $0 is not always possible for everyone, though. Many of us have mortgages on houses that aren’t worth what we were convinced to buy them for back when real estate was a “sure thing”. Not all of us find we were intelligent enough not to rack up debt in our younger years or to make our income stretch appropriately, or even to have the luxury of not living from paycheck to paycheck.

Personally, I was a freelance web designer with a ten year old son, a healthy rent payment in Pittsburgh, Pennsylvania, and my fair share of credit card debt. I made the individual choice to save money to buy an RV and get onto the road before I paid my debt down. This may have been a little risky, but my desire to hit the pavement with all four wheels rolling as quickly as possible trumped my desire to have a big fat safety net in case the highway proved a little bumpier than I pictured it every night before falling asleep. The decision proved to be the right one for my situation: once you get on the road, your expenses can dramatically decrease. Your rent becomes completely malleable, you can spend $300 / month on a spot in an RV park or, with the right setup, absolutely nothing by boondocking in free camping spots which, while sometimes tricky to locate, are ready and willing to be found with just a little online research. A cable, landline, internet and cell phone bill was reduced to an iPhone plan with AT&T and a Sprint Aircard to get online. I’d paid off my approximately $5000 in credit card debt simply by having the ability to control my monthly expenses rather than being confined to year long leases.


“We honestly did think that eventually, we would buy a home, start another business, take on debt to grow our business,” admits René Agredano, currently workamping alongside her husband Jim at a dude ranch and resort on the western slopes of Colorado’s Rockies. “…and get back to ‘reality’ once we were comfortable we had weighed all of our options while being out there exploring the country.” Instead they’ve been steadily on the road without much of any real thought given to selling of their mobility and trading in their now comfortably earned freedom for a more traditional business. Where a few dozen grand in loans could have gotten them started on building their own animal sanctuary or getting a small farm going—both previous “brilliant ideas” of theirs, as René puts it—they now run multiple businesses from their fifth wheel and get to do what they love, and try what they thought they’d love, without the commitment of getting stuck doing something that wasn’t exactly as suited to their actual personalities as it may have sounded when dreaming up future business cards.

I asked them about some of their online businesses and the various temporary jobs they’ve tried out over the years, and René couldn’t have been more forthcoming as to just how beneficial some of their mistakes have been.


“We started workamping at businesses that would give us insight on whether or not we were cut out to do that kind of work.” Workamping is a pretty broad term but generally involves RVers obtaining a free spot, and sometimes a small paycheck, in exchange for doing a few hours of work for the park’s owners. “Since we had always had a dream of running an animal sanctuary, we volunteered at one in New Bern, North Carolina. That’s when we learned that animal rescue is a noble cause, but we’re too wimpy for the day-to-day aspect. Animal rescue is hard, thankless work and it takes a very special person to do it on a full-time basis. We really admire the folks who can do this.”

a dog missing one leg is soaking wet with a stick in his mouth, presumably produced from the lake in the background
Jerry, René and Jim's inspiration to hit the road.

Instead of investing in a business they had neither the stomach nor long-term desire to be a part of, they instead began the online support network, Tripawds, for sick dogs and their people.


Step 4: Generate Income

Note that this step is not called “Get a Job” or “Make Your Money”, because, as you’re about to see, there are a plethora of ways to earn yourself the cash you’ll need for gas, beer and pizza in every state in the Continental US. These include everything from having or learning a very specialized skill, such as software development, to backbreaking work on ranches to sitting back and letting some of that cash just work its way in (eventually!).

“Later,” Jim continues my earlier conversation with René, taking a much appreciated—on my part—break from his current 50 hours per week position busting his ass on the 1800 acre ranch they’re calling home for the summer, “we worked on an organic farm during a winter in Vero Beach, Florida, since buying a small farm was another one of our brilliant ideas. René always loved gardening, and thought this would be ideal for us. But we learned that farmers are tied to their land and a ton of farm animals 24/7, 365 days a year. We knew it wasn’t something we wanted to endure.”


So what are we talking about here? A failed attempt at starting a business? Hardly, more like a trial and error approach, with nothing more than a life experience under their belt as a “loss”. This is a perfect example of why living on the road is not only rewarding for all of the Yellowstones, Pacific Oceans and San Franciscos you get to call your backyard for a few days or weeks at a time, but because you are given every opportunity you can take advantage of to find what it is that exactly will make you happy while at the same time bringing in the ever necessary dollar. You begin to look at a paycheck as significantly more than simply the number of digits and their assigned value. You begin to understand that fulfillment in your job is worth significantly more than a growing bank account, and only then can you really begin to appreciate that the dollar amount of your salary is relevant only to how you want to spend your newfound ample free time. Not to mention how hours spent working on a business or project you love often demean the very definition of the word “work”, at least as far as the “mental or physical effort” and “labor” aspects apply. You can do what you love, and don’t believe anyone who tells you that “Even doing something you love eventually gets old.” That saying often comes along with this one: “Like any job, you get used to it, get sick of it after awhile.” Spoken truly like someone who doesn’t understand that a “job” is but one of many activities you can do in your life’s career. Living on the road gives you the ability to switch up your job very regularly, and makes travel your career.


So how about some concrete examples?

I hear you, enough of me rambling on trying to convince you of why you should live the lifestyle. I know, I get carried away. Let’s finally get down to the real deal, the “How” in this “How to”. But first, a little more rambling.

You have some talents. It’s amazing what people are able to do when they’re doing what they love. People make a living posting on Facebook. Blogging used to be a word primarily used to make fun of Internet geeks, now nearly everyone I’ve interviewed takes advantage of it to either indirectly make cash by growing their business, or by actually making a living doing it (though I’ll be honest, it’s actually tough work.) Someone invented crocks, and they’re probably rich now from those fashion disasters. For every person who both wants to knit sweaters of Thanksgiving cornucopias and has the determination to market themselves, there are at least a thousand aunts and grandmas out there who are just dying for an update to their wardrobe this November. Yes, I sound sarcastic, but this is all completely true. The primary difference between people who are doing what they love to do and those who are stuck in jobs they hate in towns they’re bored of is the same difference found when comparing a photo of Brad Pitt without a shirt on and my ever more considerable beer gut: actually doing something about it.


Determine What You’re Good at, and Do That

a chart showing how long people have been on the road: 8% for less than a year, 58% for 1-3 years, 34% for 3-7 years

It doesn’t even have to be something you love. You can use what you’re good at to get you closer to what you love. Sure, most of us would like to be famous rock stars or writers or actors or famous for whatever it is that Snooki is famous for. Unfortunately, the world will always need more gas station attendants than it will Presidents, so begin looking at your life as a whole, rather than your job as your definition. If you’re a great people person but only an okay artist, well by all means, get a job running a social media business for galleries, painters and musicians and in between replying to tweets and liking things on Facebook, paint until you’ve figured out how to allow that to take over your Internetly duties. Einstein was a janitor. Columbus swabbed decks. Snooki wanted to be a vet. We don’t remember any of them for those positions though, they were catalysts, steps up on a way to doing something they actually loved.


Okay for Real Now, Actual Examples

It’s up to you to decide what avenue your personal road will become, but here are a variety of ways to actually make money on the road, with notes on which ones you can expect to get rich on, and which ones you can expect to get one helluva farmer’s tan while trimming your waist into shape for next to nothing in actual monetary compensation.

chart showing full-time travelers types of work: 72% work online, 11% in person


The Digital World

We’ll begin here, as making a living online has opened up so many possibilities. If you’re really determined to make this living on the road thing work, and you value the free time you’ll inevitably want to spend exploring the places you visit, you shouldn’t have to look any further than this list, with a dash of the principles of your own talents and desires as explained above, to find work that can at least keep you sustainable.


Antiquing
Forget the musty old three story building full of everything you can imagine except the particular type of bracelet I’m looking to get my mom for Christmas, and think Ebay. Ever watch American Pickers? What do those guys do? They travel all around and find cool stuff to sell people. Do just that, understand the ups and downs of Ebay, and you’ve got an income source.
Likely Annual Income: $24,000 @ 20 hrs/week
Prerequisites: Knowing the difference between an original Star Wars action figure and Jar Jar Binks.
Overhead: Initial cost of items purchased, likely some type of trailer dedicated to storing antiques until they sell, shipping.
Travel Compatibility: High, though dealing in things like baseball cards will be easier than armoires.
Year Round Reliability: Antiquing is usually more of a summertime activity, particularly if you forgo selling on Ebay.
Web Designer
You sit in front of a computer and create website interfaces, write lines of code, and shape the face of the Internet.
Likely Annual Income: $55,000 @ 30 hrs/week
Prerequisites: Solid understanding of art principles, color theory and design. Working knowledge of things like CSS, HTML, Javascript and PHP. General knowledge of how the web works.
Overhead: A Macbook Pro and reliable internet connection, plus some software.
Travel Compatibility: Perfect, you can work from anywhere you get an Internet connection.
Year Round Reliability: Companies need new websites and improvements to their sites made all year long.

Web Developer
You sit in front of a computer and build websites, but instead of focusing on design and pretty things, you are more involved in the “how” things work rather than “why” they work that way.
Likely Annual Income: $84,000 @ 30 hrs/week
Prerequisites: In depth knowledge of programming languages like PHP and database work like MySQL.
Overhead: Laptop computer, a steady connection to the Internet and some software.
Travel Compatibility: Perfect, wherever you can get online, you can work.
Year Round Reliability: The Internet doesn’t take a vacation, work is available all year round.
Software Engineer
You create software for Windows or Macs or, your best bet at the moment, iPhones and iPads. While there are some freelance software engineers, most work for one or more companies creating their applications rather than creating and making a profit selling the freelancer’s own software.
Likely Annual Income: $52,000 @ 30 hrs/week
Prerequisites: Serious knowledge with programming languages like Objective-C. Some design expertise may be required as well.
Overhead: A few licenses that can run $99 or more a year, a laptop and likely always the latest iDevices.
Travel Compatibility: Perfect, complete location independence.
Year Round Reliability: Very good, just as a web developer knows, companies want apps created all the year long.

Social Media Manager
You literally Tweet and Like things for a living. Companies pay you to interact with their customers via social networks, and you work to leverage those outlets to get the company more customers.
Likely Annual Income: $30,000 @ 15 hrs/week
Prerequisites: Wicked good knowledge of what drives Facebook & Twitter. Otherwise, a mobile phone could be all you need as far as equipment.
Overhead: Limited to as little as your phone but likely a laptop as well.
Travel Compatibility: Great for mostly online companies, but if you start getting restaurants and other fixed location clients, they’ll want you to be aware of actual events happening at the location.
Year Round Reliability: If you’re good at actually creating results, it’s all year round, with spikes around holidays or particular events and downtime at other moments.
Writer
You turn letters into words, words into sentences, and so on. While you may dream of writing novels, technical and travel writers are more common than novelists. There are a plethora of resources online for finding work, but there is definitely competition.
Likely Annual Income: $40,000 @ 30 hrs/week
Prerequisites: Grammar, punctuation, ability to get your email noticed over 100 others in an editor’s inbox.
Overhead: A laptop.
Travel Compatibility: Excellent, you can write from wherever you can write, so location should not be an issue. If you’re a travel writer, it’s essential!
Year Round Reliability: There is always work for a writer, regardless of season.

Life Coach
You help other people to set goals for themselves, and then coach them through the steps needed to make those goals come true. You’re like a therapist who urges people to get off the couch and do something about their situation.
Likely Annual Income: $45,000 @ 20 hrs/week
Prerequisites: People person skills, outgoing, seeming to have a grasp on your own life’s issues.
Overhead: Very little other than what you create.
Travel Compatibility: While some life coaches are able to work with their clients over the phone, most meet them in person and some even have offices where their clients come to them.
Year Round Reliability: People have problems to sort out and goals they want to achieve all year long.
Accountant
You assist people in keeping their affairs in order, and for a few months a year bury yourself in others’ tax forms.
Likely Annual Income: $40,000 @ 30 hrs/week
Prerequisites: Great with numbers and forms, likely a degree or at least experience in accounting and tax preparation.
Overhead: Possibly a school loan you would have had anyway, as well as licenses, fees and software.
Travel Compatibility: The heaviest portion of the tax season is only for a few months a year, so even if clients want to see you in person, you’re largely free after April 15th. Establish yourself in one particular location where clients can meet with you during those months and explore the world the rest.
Year Round Reliability: The first few months of the year will be the most profitable, but a good accountant can work all year long.

Offline Work – for those who don’t want to work on or can’t stand the Internet
Craftsman
You create high end work, such as remodeling someone’s home or RV, framing pictures, or building someone a gazebo in their garden.
Likely Annual Income: $27,000 @ 40 hrs/week
Prerequisites: Ability to work with your hands to create something beautiful. Mechanical inclinations.
Overhead: There is quite a bit. Tools and the materials for what you are working on, plus you will likely need a license for larger projects.
Travel Compatibility: Fair, depending on what you do and how you market yourself. Some projects will require you to remain in one location for longer periods.
Year Round Reliability: Less work available in the winter months, summer and fall are peak seasons.
Migrant Farmer
You work on a farm milking cows, fixing tractors, mending fences and bailing hay, as well as any and every other random job one might imagine a farm requires.
Likely Annual Income: $12,000 @ 50 hrs/week
Prerequisites: Strong back, lack of hay fever, ability to work with smelly animals and do dirty work over long, long hours.
Overhead: Very little, most farms will supply you with what you need.
Travel Compatibility: Limited. Though the title contains the word migrant, you’ll likely work one or two longterm jobs per workable season.
Year Round Reliability: There is work available year round around the country, but the majority of work is available from mid-Summer to Fall.

Hotel Worker
You clean rooms, primarily, though there may also be kitchen or front desk type work involved.
Likely Annual Income: $18,000 @ 40 hrs/week
Prerequisites: Affinity for housekeeping.
Overhead: Little to none.
Travel Compatibility: Not great, depending on how often you would like to find a completely new job, as this is definitely one of the most location-based positions on this list. However, you can find work seasonally in places that are more popular at certain times a year (think working Lake Tahoe in the Winter and Myrtle Beach in the Summer.)
Year Round Reliability: text
Painter / Gardener / Handyman
You paint people’s houses, mow their lawns and fix their leaky pipes.
Likely Annual Income: $18,000 @ 40 hrs/week
Prerequisites: Steady hand, strong back, general knowledge of how things around a house work.
Overhead: Paint, brushes, tarps, etc. String trimmer, riding and push lawnmower. Tools, tools, tools.
Travel Compatibility: Again, this is dependent on how well you can market yourself in a new location. Much of this work is seasonal, though, so expect to work more in the warmer months and have more opportunity to travel in the Winter.
Year Round Reliability: Wavering, more work in the Spring, Summer and Fall.

Seaman
You work on boats seasonally, from swabbing decks to making food to cleaning rooms to removing barnacles.
Likely Annual Income: $16,000 @ 50 hrs/week
Prerequisites: Sea legs, knowing your port from your starboard, knot tying.
Overhead: Little.
Travel Compatibility: Fairly good particularly if you work in the Caribbean, but opportunities everywhere from the Great Lakes to Alaska.
Year Round Reliability: Pretty great as you can find work in the Caribbean in the colder months.
Amusement Park Worker
You sell popcorn and cotton candy to kids, clean toilets, slap wristbands on families coming through the gate, and clean more toilets.
Likely Annual Income: $5000 @ 35 hrs/week
Prerequisites: Pushing a button on a ferris wheel to make it go around and around, general mechanical know how, housekeeping and service industry experience.
Overhead: Minimal. You won’t have to buy a Mickey Mouse suit but you may be required to purchase specific clothing.
Travel Compatibility: You’ll be stationary while you’re working, but given the seasonal nature you can get around.
Year Round Reliability: Poor, most amusement parks are open only in the summer months, though there’s always Florida and Southern California.

Summer Camp Worker
You help guide kids into leading healthy, respectable young lives during the day, and party with your fellow camp counselors in the evening. Expect to be involved in lots of canoeing, hiking and capture the flag.
Likely Annual Income: $4000 @ 35 hrs/week
Prerequisites: Good with kids, outdoor skills, fit physique.
Overhead: Very little.
Travel Compatibility: You can get work at multiple camps every summer as most gigs are only for a week to a month. Plenty of (unemployed) time during the rest of the year to spend that cash, though…
Year Round Reliability: Not great. Even in warmer climates, kids are in school from September through May, so this is really just one job you could do for the summer months.
Photographer
You try and take photographs that are better than 99% of what’s on Instagram, for magazines, journalists or companies, primarily. You attempt to sell some of your own work on sites like iStock Photo or via your website
Likely Annual Income: $35,000 @ 40 hrs/week
Prerequisites: Ability to work a camera, Photoshop knowledge, understanding composition, comfortable getting up in people’s faces.
Overhead: Camera equipment can be costly, a laptop, Photoshop. Much more if you decide to go with film vs. digital.
Travel Compatibility: Very good, particularly if you’re a landscape photographer, but depending on the kind of work you bring in, you may be required to go to particular places vs. having complete freedom to travel wherever you want to go.
Year Round Reliability: A photograph of snow can be just as gorgeous as one of summer flowers.

Musician / Busker
You either play paid gigs at bars or festivals, or you create your own shows by setting up on street corners.
Likely Annual Income: $26,000 @ 30 hrs/week
Prerequisites: An ear for music. Songwriting or good taste in covers.
Overhead: Your instrument, amps, microphones, etc. Strings, picks and drum sticks. Possibly tattoos.
Travel Compatibility: What’s the definition of “Going on Tour” again?
Year Round Reliability: There is definitely more opportunity to play music in the summer, and busking in Winter can be tough work, but there’s year round potential.
Au Pair / Nanny
You take care of other people’s kids, clean the house, make them lunches, escort them to the park and try not to teach them to swear.
Likely Annual Income: $6,200
Prerequisites: Good with kids, having at least a few motherly bones in your body.
Overhead: Very little and you’re usually compensated for anything you have to spend extra (like ice cream cones).
Travel Compatibility: As this position is much more likely to be found in Europe, you could take advantage of that and travel quite a bit. In the US, Nannies are expected to be long term.
Year Round Reliability: Great…if you want to travel less in the US than you do in other countries.

Tour Guide / Adventure Guide / Walking Tours
You learn everything there is to know about a particular area and drive, peddle or walk them around an area. This could include an historic part of a city or backcountry wilderness.
Likely Annual Income: $27,000 @ 35 hrs/week
Prerequisites: Lots of historical and cultural information about various locations. Comfortable speaking in public and either a good driver or great hiker.
Overhead: Legal forms, a vehicle if you’re not doing walking or hiking tours, emergency kits, sometimes food and spare water for your customers. Time spent researching locations and planning routes. Local and state fees for licenses may be required.
Travel Compatibility: Great. Since there are a plethora of tourist areas in the country, you can change up where you work as time goes on.
Year Round Reliability: Fairly good, as different areas of the country are more prone to tourism at different times of the year (ie, New England in the Fall, the coasts in the Summer, the Smokies in the Spring and the South in the Winter.)
Housesitting
You either live in someone’s house temporarily while they’re on vacation, away on business, etc., or you just stop in and check on things a couple of times a day.
Likely Annual Income: $5200
Prerequisites: Basically, the ability to exist. Possible need to be good with dogs (ie, feed and walk them), and to easily decipher how a strange television remote control works on a regular basis.
Overhead: None really.
Travel Compatibility: Excellent, considering people have houses in every single county of every single state in America. Plus, for travelers who don’t roll with their own RV, it’s a free place to stay as well.
Year Round Reliability: You may find that people looking for a housesitter are doing so at a time when their particular hometown is not “in season.” Lining up steady jobs one after another is tricky.

Teacher / English Tutor
You are either a substitute teacher in areas of the country that don’t require a license to do so, or you specifically tutor people in a language, such as English or Spanish. Some teachers also make money as personal coaches, or lesson planners, for homeschooling parents.
Likely Annual Income: $20,000 @ 20 hrs/week
Prerequisites: Knowledge and prior teaching experience. Possibly a second language.
Overhead: Materials and supplies can be kept at a minimum with the help of email and computers vs. paper and pens.
Travel Compatibility: Finding substitute teaching jobs may require you to establish a physical presence for yourself for much of the year, however summers would be naturally open. Tutoring or creating lesson plans for others is considerably more lenient on location and timeframe needed per job.
Year Round Reliability: Again, it depends on which variety of teaching you take up, but there is typically work year round, even as the summer will be less fruitful.
Campground Host
You park your RV in a particular spot of an RV park, usually at the entrance and rarely in one of the “sweet spots”, and help the other guests who are visiting remember to turn down their generators, collect their camping fees, clean up trash, and generally be a source of information to your fellow campers.
Likely Annual Income: $5000
Prerequisites: Simultaneous ability to chit chat with strangers and later that night tell them to turn their radio down. Patience, willingness to be available just about all day long, and your own RV.
Overhead: Not much aside from the cost of your RV.
Travel Compatibility: You will need to move around at least a few times a year, as you follow the seasons, but since most parks want you to stick around for more an entire season, it could limit you to only a few places a year (which is often what full-timers end up doing anyway).
Year Round Reliability: You’re much more likely to find work in the summer, and will be confined to Florida, Texas, etc. for most of the winter, if you can find a position during the slower months.

Crafter
You make something interesting that can actually turn a profit for the time you put into it, like wooden rings or vintage looking jewelry or punk rock stockings, and sell them online and in various real world markets.
Likely Annual Income: $9000 @ 30 hrs/week
Prerequisites: Being an “arts & crafty” type.
Overhead: Materials that can range from raw metals to fabric to rare finds at thrift stores.
Travel Compatibility: As most crafty items are small and/or light, and require only a small workshop or creative area to produce, quite well.
Year Round Reliability: While Christmas might prove to be a busier season than others, people shop Etsy and go to craft shows all year round.
Masseuse
You rub other people’s backs.
Likely Annual Income: $20,000 @ 15 hrs/week
Prerequisites: Strong hands made of butter, knowledge of the human anatomy.
Overhead: Special table or chair for clients, oils and perhaps other additional supplies used to set you apart. Many areas do require a license of some sort.
Travel Compatibility: Okay, the licensing issue can present real problems with going anywhere, but there are ways to negate that as well.
Year Round Reliability: I like a massage regardless of what day of the year it was. I’d like one right now.

Debunked

The following are commonly “recommended” around the web as great ways to make a living while traveling. We call bullshit, and so did the people we spoke to who’ve tried it.

Traveling Food Cart
You dedicate part of your rig to the needs of a commercial kitchen. While a gorgeous idea in theory, and a previous idea of my own, the issue is getting the necessary permits required to operate within the various laws of every random place you’ll visit. However, if you want to travel a “circuit”, where you go to particular cities or county fairs, etc., well you might just be able to pull this off.
Workamping
Basically a broader term for campground hosts, which we discuss above, nearly everyone we’ve spoken to about workamping has agreed that it pays way too little for way too much expected time, and the free camping spot doesn’t provide enough of a balance to make it all worth it.

Blogger
Not that you can’t make some money blogging, and not that there aren’t professional bloggers, but while almost everyone I spoke with made some type of income from blogging, only one person did so exclusively (and admittedly, even they did some additional travel writing). The primary difference between a writer and a blogger here is that writers typically do some substantial part of their work for other companies, while bloggers, in this case, are just writing their own blog(s).

Other Ways to Generate Income

While the ideas above are actually longer term jobs you can pursue as part of a one or two pronged solution to making enough income to live and work from the road, the following is a list of things you can do to make a little extra cash here and there. You probably won’t make it rich with any of these, though.

  • Donate Plasma Don’t mind exchanging some precious life blood (literally) for $35? Hello free cookies!
  • Online Advertising / Blogging You probably aren’t going to become the next professional blogger, at least not overnight. However, there is money to be made from online advertising, even as much as a few hundred dollars a month after you’ve put in some pretty serious effort to creating a website worth advertising on.
  • Art School Models Take off your clothes in front of a bunch of art students and sit relatively still for an hour while they draw every last one of your curves. If you’re okay being naked—and keep in mind that it isn’t necessarily about having the perfect body from society’s typical viewpoint, curves are great for students learning to draw—you could bring in about $20 – $40 an hour. Not bad money, though you’ll be hard pressed to make a full time gig out of it.
  • Kissing Booth Pucker up and charge a buck! Might want to add a lemonade stand on the side for an extra quarter or two.

Step 5. Hit the Road, Get Used to It, and Be Available!

That last bit there seems to be the most important. It’s easy to get caught up in ditching work for the day to explore the Grand Canyon, but after three weeks of making it down to the Colorado, kayaking, and fighting your way back out and up, you may find your inbox flooded with emails that start out as “I need a project done”, followed by “Are you available?” and finally “Nevermind, don’t bother writing us back.” Nearly everyone I spoke with mentioned how they’ve learned to be responsive to clients and, when they’re away during “normal working hours” for days at a time, to set up simple auto-responders informing their clients of such.

There are bound to be growing pains, and even growing highs, as you hit the road and discover how to run your particular brand of business. This applies to both those folks who are starting a new venture as well as people transitioning from a sedentary freelance lifestyle into a traveling one. Don’t be afraid to mix things up, to experiment, and to try new things.


The Final Step (6). Realize You Don’t Ever Want to Stop

If you can get your rhythm and keep the income flowing, you may very well become one of those people who “don’t see any end in sight.” While many people we spoke with ended up settling down while they were pregnant, many of those hit the road again. Some people find that place they simply love and, often having seen nearly every county in every state, decide to give a more traditional sense of community a go. That’s the beauty of this lifestyle, there is neither a time limit nor do you commit yourself to it for life.

Just in case you haven’t found yourself quite convinced at the plausibility of it all, and let’s face it, if you’ve come this far, you’re as good as on the road, we have a few stories from actual families and individuals who are on the road even as you read this.


The Road Forks

Meet Akila and Patrick, two travelers who, as they put it on their website, “are cooking and eating our way around the world.”

When not writing about their travels and all-around-the-world inspired culinary delights, Akila is a legal aid and Patrick a software architect. Both work remotely, because they are literally traveling the world full time. A few years back, they sold their home in the United States and began moving from country to country, renting as they went.

“All of our clients are US based,” Akila tells me, “I was a lawyer before I started traveling and Patrick is continuing to work for the same company he worked for before we left the U.S.” While she has transitioned her full time position as a lawyer into skills more friendly to living in Italy one month and Bulgaria another, Patrick was able to leverage the value that he’d proven to his company while working as a “regular” employee into a successful remote position.


I asked her about the amount of planning they did before setting off to voyage this spinning round globe. “None,” she states simply, “We didn’t really think that we would be able to make an income while traveling—we have been pleasantly surprised that people like our work enough that they keep wanting to hire us while we travel.”

They’ve lived everywhere from Australia to Canada, Ireland to Japan. Switzerland, South Africa, Croatia, the list is impressive and more so, impressively varied. I asked them about the expenses of all of this nation hopping.

“We could travel much cheaper by staying in Southeast Asia or South America, and we try to balance expensive countries with cheaper countries. For example, in the last six months, we spent one month in Croatia, one month in Bulgaria, and two months in Turkey to offset five earlier months in England, Spain, France, and Italy.”

I know, sounds rough, right? I’m kidding, of course, but when asked about the difficulties of transitioning over the years, her biggest complaint: “When we don’t have fast Internet for a few days, we start to get very nervous.”


Understandable for a couple making their living online. They admit to occasionally working 60-hour work weeks to pick up the slack from periods where they barely work at all, particularly in more expensive locals, such as ancient and ethereal Cappadocia, Turkey, where it makes more sense to get in, do it, and get back to cheaper rent.

“When we have friends or family staying with us or we have limited time in a particularly expensive location, we end up working less than 10 hours/week.”

the expansive landscape of Cappadocia's pigeon valley, peaking mountain, blue sky and a trail through rolling hills
Pigeon Valley in Cappadocia. Photograph by Benh LIEU SONG

Akila has some advice for anyone who’s looking to make a living while traveling. “Make sure that you do exceptional work every single time you get a contracting gig. That’s the only way to survive as a freelancer.”

Though they initially traveled by airplanes and buses, they’ve recently shipped their SUV, and two dogs Chewy and Abby, to Europe where they’re roadtripping their way through life. Currently they’re in Naxos, Greece and looking towards Athens.

Akila and Patrick of the Road Forks standing in front of a building which I assume to be the Taj Mahal...
Akila and Patrick of The Road Forks
Read the full interview with Akila on our blog.

Living Lightly

Matt and Sara Janssen hit the road on their Living Lightly tour, doing demonstrations of the vegetable oil system in their RV at colleges, coops, and festivals for a year.

“I also did a lot of photo shoots for families and couples and Matt did remodeling work.” After the tour, Matt continued in the construction line of work and began doing veggie oil conversions for other people in search of a cheaper way to power their engines.

“In the Summer of 2005,” Sara continues, “we were staying in a hotel for four weeks for business. We had a small suite that had a bedroom and a little kitchen. We realized while we were there that we were extremely happy living in a smaller space. We liked knowing where Bella,” their, at the time, three year old daughter, “was at all times without searching. We liked that cleaning up only took a few minutes instead of an entire afternoon. It just clicked.”


They talked things over, sold their newly-purchased home in Des Moines, Iowa, and seriously downsized. “We spent entire weekends cleaning out our basement, selling things on eBay and Craigslist. Slowly, we came out from under our self-imposed weight of possessions.

“In that time, we also had a strict budget and paid off all of our consumer debt.” It took them a year to pull it all off, “but by the end of that year, we had paid the debt, sold our house, and moved into a smaller apartment.” Then they began reading a book by Shane Claiborne, Irresistible Revolution: Living as an Ordinary Radical. In it, she explains “Shane talks about what life would look like if Christians actually lived out what Jesus taught. He and others live in a community called ‘The Simple Way’…and they ‘attempt to live like Christ and the earliest converts to Christianity, ignoring social status and unencumbered by material comforts’. This book was a major catalyst in our desire to make a change…”


They began reading blogs about simpler, greener living, and came across the social movement known as The Compact, where followers promise not to buy anything new for a year. New is used literally their, you can still purchase previously owned goods and of course necessities like food. On her blog, Walk Slowly Live Wildly, Sara explains the rules she set for herself when attempting the Compact.

I will not buy any NEW items for one year. I will only buy items that I NEED. I will not buy any convenience foods when grocery shopping with the exception of bread and chips. I will strive to eat in season, buying as local as possible. I will bring cloth grocery bags to the store, and I will create a weekly menu/grocery list EVERY week.
I will not go out to eat at a restaurant if I have the option of eating at home.

“We loved the freedom we felt in giving things away,” she says, “helping others, and feeling the wonderful ‘light’ feeling that comes with getting rid of things that you don’t need.”


She reminisces a moment on those days back in middle of the last decade, before they’d even begun their days of nomadism. “The group of friends we had in Des Moines were also instrumental in our journey…so many wonderful, thoughtful families, encouraging each other to make slow changes.”

Still, something didn’t seem right. They decided to give up their jobs, which paid well but weren’t quite as kind on their spirits, and move to Bozeman, Montana in search of a simpler way of life. As she tells it, “It was a great time of reflection, rejuvenation, and searching out what God had for our lives.”


The Janssens in their RVing days, standing in front of their rig
4/5ths of the Happy Janssens

It was a back and forth time. At one point, before moving to Bozeman, they’d purchased a beautiful bright yellow 1977 Volkswagen Bus. “A gorgeous Westy,” as she puts it, referring to the nickname Bus owners apply to those vehicle which have been modified into campers by the Westfalia company. “We had planned on traveling the country in it,” but instead sold it during their downsizing days, “but the traveling lifestyle was still calling to us. We were always talking about how we wished that we would have ‘just done it’.

“We decided to follow our hearts. What is the worst that could happen by pursuing our dreams? Failure? No big deal…at least we can say we tried! And in the end, we’ll have no regrets.”

a yellow 1977 Volkswagen Bus with the Westfalia pop top up, in a grassy field against the blue sky
The Janssens former VW Bus.

So they, along with their daughter Bella, hit the road. They traveled the country for four years, with a brief intermission to have their second daughter, Lucy. They all currently live in Longmont, Colorado, along with yet another beautiful little girl, Emma. I asked her what the impetus for their decision to settle down was.

“We had a job opportunity that was too good to pass up, and we also had a lot of friends and family in this area. Longmont is a very family friendly and affordable city…close to the mountains, Denver, and other recreation. We love it!”

I think that strikes on a wonderful point to all of this working, living and traveling. While it may take awhile, years even, for people to gather the nerve and logistics to get onto the road, when you’re ready to come back to the world of the “settled down”, it’s ready and waiting for you.


Life Remotely

Kobus Mans left his native South Africa to work on Norwegian Cruise Lines where destinations like the Mediterranean, Caribbean and Alaska were on his life’s regular rotation.

While sailing around the world on floating cities, Kobus met Jessica McCafree, who had come to work on for the cruise line as a photographer, having already spent plenty of time traveling Europe doing things like photographing archaeological digs in Croatia. Along with Jessica’s brother Jared, a mobile application developer who finished high school in the Netherlands and returned to Holland to study Dutch during his college years, the two—who are now married—set off in October of 2011 from their home in Seattle, Washington for a longterm roadtrip.

To Antarctica.


“I am a freelance graphic designer, specializing in PowerPoint design.” The three rely on International cellular data plans and free WiFi cafes for their connection to all things Internet. “I have several clients back in the Seattle area that contact me for small projects and I have one client where I work as a contract designer with their in house team. I am essentially the overflow designer. Where there is too much work for the team to handle, they push the extra to me.”

Her brother is a software engineer. Her husband is a web designer who does some freelance work, “but most of his income is from teaching.” Jared works part time for Lake Washington Institute of Technology.


“For all of us, this is what we did before we started traveling,” she writes. The three are currently in Colombia, waiting for their vehicle—a 1997 Toyota 4Runner they call Blue, after it’s paint job—to arrive. They had to ship it from Panama as there’s a stretch of the Pan-American Highway that has yet to be completed. She continues, “We had to change the type of projects we could take on and the amount of work we could accept. For example, more than half of my business used to be working backstage at business conferences operating the graphics.” Changing the type of work they would do while on their epic journey through the Americas wasn’t the only transition.

Referring to their first month or so transitioning to working from the road, “It was rough, but not unbearable. The issues that arose were more between us as a travel team than for our bosses and clients. We struggled with finding a balance between working and traveling. Eventually we set designated ‘work days’ which helped us to keep things on schedule. Also, we set strict limits about the number of hours each person could work,” in fact, they thoroughly planned not only their work schedule, but how many days they’d spend where and what everything from food to freeways to fun would cost them. “Putting the entire trip on hold because one person over committed to a project was messing up our travel style. I’m now on a 15 hour work week.”


three young people in a shipping freight yard, there blue 1997 Toyota 4Runner in the background
All three folks from Life Remotely

In fact, Jessica says that they actually saved up enough money prior to leaving to support the entire trip. “We consider the work we are doing now,” she says, “the savings for our next trip.”

The trio are currently waiting with a pair of bolt cutters for the crate their 4Runner is in to meet them in South America. “If all goes well we will continue this adventure to another continent.”


The Professional Hobo

Nora Dunn took a leap of faith.

You could say she was a famous financial planner. When the news needed a talking head to discuss the ever urgent changing atmosphere that is moving money around in a manner that will keep people feeling secure in their wealth, they called on her. She had stood in front of rooms with as many as 3000 other individuals, all focused on her wisdom in the arena. She worked for the largest financial planning company in Canada and ran her own practice, pulling in six figures a year. Then one day she broke the news to her boss. She was giving it all up and heading to Costa Rica.

They asked her to stay, offering her a few months or a year to go sort things out while they took care of things. Her job would be waiting for her when she returned to Toronto. Tempted, she quit anyway, and through a series of events ended up beginning her travels in her home country of Canada.


“Despite ‘planning’ being an integral part of my personality,” Nora, who calls herself the Professional Hobo, tells me, “when I sold everything to travel I had no idea where I would go, what I would do, or how I would make money on the road. All I knew was that I had to travel.”

That was in 2007. Since then she crossed continents by train, survived bush fires in Australia, disappeared in Hawaii, loved and lost, helped cyclone victims in Burma and called oceans her front yard. As she writes on her blog, “I still feel like an infant in some respects, and like a sage prophet in others.”

She says she hit the road in completely uncertainty as to how she would make a living. “I ended up parlaying my financial expertise into the travel realm, and my lifelong knack and passion for writing was a great medium for it all.”


“I had a nest egg from my previous years of saving while running my business, along with some retirement savings socked away for a day when I won’t be able or willing to work. But I haven’t had to dip into either.”

“It was in the first few months of hitting the road that I had [an] epiphany!” She’s speaking of realizing that she could make a living as a writer from anywhere she could get an Internet connection. Two years of nearly full-time work with no income later (she lived off of the money from the sale of her practice back in Canada), she had crafted herself into one of the pioneers of professional blogging.

“This was back in 2006, when location independent careers weren’t the norm, and blogging wasn’t a recognized industry. I think it’s still very much evolving and developing, and it has been exciting to be on the leading edge of it all.”

Though she’s still not making close to six figures—last year, she openly states on her site, she made $21,000, and is on track to double that this year—she hasn’t had to wait until age 65 to live in Australian National Parks, hike the Scottish highlands, walk through castles in France or sail the Caribbean for six weeks.

Nora says she works about 20-30 hours a week, and like nearly everyone else we spoke with, has days in a row she doesn’t work at all and some where she’s at her computer for 10 hours straight. She’s now at a point in her mobile career where she doesn’t need to seek out work anymore, it finds her.


sepia toned photo of Nora Dunn, aka the professional hobo, with blurry pedestrians behind her
Nora Dunn, the Professional Hobo

“My biggest challenge that I constantly face is the feeling of guilt that I harbour for working and not getting out there and discovering all those exciting things outside my window. But then again work is work regardless of where I am in the world. When work is done for the day I close my laptop, look up, and realize I’m in a completely different place in the world. That’s when the fun begins.”

She continues, “This is also why I’m a proponent of slow travel; it gives me a chance to discover a destination slowly and organically—while also staying on top of work—instead of tearing through as a tourist then collapsing somewhere from exhaustion and needing time to recover and catch up. I think it’s all about balance.”


5 O’Clock

We’ve talked about how and why. We’ve listed actual positions people partake in to make mobile living a reality. We’ve shown stories of a variety of types of people doing a variety of work while on the road. We’ve had lots of graphs along the way. Therefore, we’d like to think you’re ready to finally make the next step, the one where you start off on a highway and don’t look back. However, if you still would like more information, feel free to contact us, we’d love to help try and answer any of your questions. Just hit us up on Facebook or Twitter!end of article

Credits

Nathan is the Editor-in-Chief around these parts, and has been traveling by train, bike, VW Bus and Airstream since 2008. He's on Instagram.