Coming of Age in the Virtual World: A How to Travel Full-time Guide for Young People

a man backpacking the world

Photo by Faungg


Your wanderlust is begging to be pacified, but you haven’t been able to turn down the dial since the signals began.

Dreams of traveling by foot, van, motorcycle, bicycle, car, train, bus, or any means possible came knocking at your door and won’t seem to leave you alone. All of a sudden the life you once seemed to love–your home, your loved ones, your job–feels less authentic and makes little sense. I was in that very same head space seven years ago, before I hit the road with a backpack never looking back. Ahead, all you can see is the vast wilderness, untethered adventure, the unknown. You want it so badly you can taste it. But you haven’t the faintest idea how to this dream come true.

Believe it or not, traveling as a way of life has never been so easy. The economy is tenuous. Day jobs are hard to come by. The rat race is growing tighter by the minute, and you better not step out of it or the next go-getter will be at your heels ready to take the crappy job you never wanted in the first place. What’s a boy or girl to do? Ten years ago, this question had an easy answer: stay and suck it up. Sell your soul for the rest of your life to pay the mortgage and lease on a car that you only kind of like, for no good known reason other than “that’s what I’m supposed to do”.

Well, guess what boys and girls? Times, they are a-changin’. You just happen to be alive during one of the greatest eras in history, when everything you need is at the tip of your fingers, literally. That’s right, everything you need is accessible through the web. And there are thousands of niche jobs to accompany the digital age.

The term amongst inner circles of travel-for-a-living folk is “digital nomads”, or a less popular but just as applicable, “virtual gypsy”. The trend began over a decade ago without any label. People left their homes to travel for extended periods of time. The internet–accessible back then in the occasional ahead-of-their-time internet cafes–meant travelers had means of accessing funds, online work, or managing their business remotely. Being a digital nomad then was less popular because it was still difficult. It was more a necessary means to an end. Today, however, you’re coming of age at the peak of the virtual world.

My first encounter with a digital nomad was a gentleman who had been living on the same secluded beach in South Thailand for over ten years…without working. Today, his label would be more likened to “beachside entrepreneur” given his locale. In his prior life, he wrote software for the US government, and then wrote his own coding system, selling it for a fair sum of money. After investing the money, he took off to travel, landed on that beach, and has been living as a retired 30-40-something ever since.

Granted, this scenario is a little far-fetched since not all of us are brilliant coders. Fear not, there are other ways to live your traveling dream!

For me, the path was less straightforward than the gentleman described above, much of it I discovered after the fact. Below is a step-by-step plan to set up your digital nomad lifestyle that you may not need make the same mistakes. Some of the concepts extend beyond digital and are simply supportive of nomadic journeying, but nevertheless gems to keep in mind and may just be the key to changing your life.

Step 1: The Internet

Acquire a smartphone and a small, light computer like a MacBook Air. It’s what I use and love after trying other, less desirable options. There are an increasing number of co-working spaces to support the digital nomad lifestyle then available, to compliment the typically free access you’ll find at coffee shops. WiFi is widespread even in far corners of the world. Or in countries with prolific cellular service, use your international provider for constant connectivity.

Step 2: Destination

Figure out where you want to go! This is the moment you’ve been dreaming of; it’s time to hit the road. Do you have a plan in mind? You may just be a go-with-the-flow traveler, content to take tips from fellow travelers you meet, or you may plan the entire thing out before leaving. None of these details matter. All that is important at this stage is that you have a dedicated starting point, an idea of where you wish to head, and you pack appropriately (bring winter clothes if you plan to trek into snowy mountains, a bathing suit for surfing, and pack lightly if you will be carrying your pack on your back by foot, for example).

Step 3: Work

You’re doing all of this for the travel, but at some point you’ll need to work along the way and it’s time to give some thought to what you’d like to do, and what is plausible. This will require some serious creativity and willingness to step out of the roles society has shaped for you–or you’ve created for yourself–like “nurse”, “lawyer”, “assistant manager”, and so on. Unless you are a doctor and plan to join Doctors Without Borders, it’s time to think outside of the box. Take a deep breath, open your mind, and begin to get excited about creating your brand new life.

If you have decided to move to a new city for a few months, and then another for another few months, this step is important but less crucial since you will have time to build contacts. Keep in mind, though, that travel and time warp co-exist, so those three months will fly by. If you’re someone who wants to move a lot while you travel, now would be a good time to explore what types of jobs are available online. That is assuming, of course, that you plan to work for someone else instead of building your own dream (covered in a little while).

Searching online, there are a few key terms to keep in mind: freelance and contracted remote positions. Ideal organizations will not mind where you’re located, just that you get your work done on time.

How in the world do you figure out what to do for money? Now is the time to get creative and adventurous. Discovering hidden talents and boosting self-confidence in relation to unexplored skills can be as liberating and exciting as traveling itself. Most designers, writers, entrepreneurs, and artists have no idea they are talented, until they have no other choice but to give their art a shot. If you have any doubts about my claim, a great book to pick up for anyone is “The Artist’s Way”.

Believe it or not, this is precisely what happened to me. Although I have been writing creatively and academically for years, I always brushed my abilities aside. My sister has been an award winning, published writer since the age of thirteen. Instead of taking into consideration that I may have her same genes, my go-to excuse for avoiding writing was always, “My sister is the writer in our family.”

It’s just easier to hide in the shadow of our true selves. If you have even a tiny bit of money saved up, now is the best time to explore your talents and see what is hiding in your shadow self.

Step 6: Job Resources

Companies post positions routinely on job boards like Craigslist and Monster for freelancers. Then there are popular freelance sites for digital nomads such as,, and All of these websites also offer smartphone apps, so you’re never too far from connecting with clients, or learning about the latest available job in your niche. If this is the first time you are hearing about these resources, you’ll be pleasantly surprised at the broad range of jobs offered; everything from freelance writing, editing, translation, data entry, and web design, to administration and remote sales jobs. How about editing a cookbook or ghost writing a children’s story for someone? Maybe these jobs seem less glamorous than you’d hoped, but it’s an opportunity for remote work that has the potential to cover traveling expenses.

At this point you may be thinking, “I am unskilled and these options won’t work for me.” I hear you.

The next best thing to being a freelancer is to doing what you do naturally; speak and teach others to speak English! While there are endless ESL teaching jobs overseas (English as a Second Language), most readily found on job boards depending on the country you wish to visit, nowadays there even online English Teaching platforms! Fill out an application and get hired with an online ESL service to teach English to their clients. No marketing, only teaching. is one example.

Step 7: More Ways to Make Money while Traveling

A lot of these options will depend on your self-motivation, drive, creativity, entrepreneurial spirit, and openness to uncertainty.

With online crowd funders popping up left and right, there is no shortage of ways to raise funds–for anything. It’s a simple matter of how creative you are willing to get. One of my friends cycles around the world. He funds his trips by raising money via crowdfunder campaigns on Cycling not your thing? If you are a traveler, there is a 95% chance you have an idea of some sort that you would love see become reality. Traveling is the perfect time to make your dream happen. You’ll have time to pour all of your heart and soul into a campaign, gain support, fans, be able to test the viability of your concept, get feedback, and most importantly, secure local media coverage wherever you go.

If you’re crafty, Etsy is the world’s largest online marketplace for handmade goods. You’ve heard of it, and so have all of your friends, family and neighbors. If you make anything at all, consider selling it here. Their Google SEO works for you, though I do recommend joining Community Teams and self-promoting your goods for additional sales. You might even find vintage collectibles from each city you visit to sell.

If you find passion and skill within the world of art, design or fashion, perhaps you take your love on the road with you, literally. In my hometown, Cleveland, Oh, a man sets up his vintage clothing shop in our weekly West 25th Street hipster Saturday market during the summertime. His shop doubles as his home; a dope, silver bullet, old-school VW van. Autumn leaves begin to fall, and he motors his way across America, selling as he goes, until he reaches California where he sets up for the remainder of the winter. Forget pop-up food carts. Craft and clothing pop up shops in the form of a “cart” are the hottest new trend sweeping the globe.

I will share one more way for you to make a living as you travel. One word: Skype. Skype revolutionized global communication and our ability to make a living from anywhere in the world. Have you ever considered becoming a life coach? How about a fitness or nutrition coach? If you already have the training and certifications, now is the time to elevate your business to the virtual landscape. You can offer Skype sessions of any sort from anywhere in the world, as long as there’s a strong Internet connection.

The truth of the matter is, with a tiny bit of brainstorming, a day or two of online adventuring, a lot of courage, and self-drive, you can do anything you set your mind to. It’s up to you to decide how much time you wish to dedicate to work while traveling, how integrated your choice of work has to be with the traveling, and what all you are willing to do to support your travels in the long-run. The longer you travel and the more people you meet on the road, the more ideas you’ll have about alternative lifestyles and means of income.

If this article has helped broaden your mind about life possibilities, career possibilities, and given you courage to take the necessary steps towards travel, then my job is done. I wish for you happy, safe, adventurous, passion-filled, soul-fulfilling travel and work.