The Professional Hobo

How do I make money on the road?

I make money on the road with writing. I write for both online and print publications, however my “break” into the industry was through the online medium. This is ideal for travel, as I can make a living with an internet connection anywhere in the world. This is called location independent living.

Where to next?

I tend to follow my nose, and have learned that making travel plans too far in advance can mean forsaking a sometimes better opportunity that arises by virtue of simply keeping my eyes and ears open…and traveling.

How did I get into writing? (And in turn, how can you)?

I am asked this question regularly, by people both gifted with words, and not so much. Some people with an entrepreneurial sense see an opportunity to make money from anywhere, but they may not be the world’s greatest writers. Others are dedicated to writing as their craft and want to know how to break into the industry.

Some writers will tell you that you first have to be able to write before making a living at it, while others say that writing is not as complicated as you may think and that success in the industry is far more connected to proper networking and following a formula (usually as set out in a course they are selling) than any intuitive talent.

I believe you need both. I once read about a famous writer addressing a university journalism class about to graduate. He posed a mind-numbing question to the class: “Why do you write?” The students hummed and hawed. The answer “to make money” came up, to which the lecturer responded that the average writer makes $6,000/year, so if anybody in the classroom writes to make money, they had better leave now and find a new career. “For fame” was another response, which was again shot down by a statistic indicating that the vast majority of writers never see their work or personas revered in a fame-supporting way. The guy who said “To tell the truth” was laughed out of the room.

So why do you write? The answer to the question was simple: Because you have to. You simply have to. It is in you to write, and you have no choice but to write. Whether or not you make money with it is almost irrelevant. (Try to tell the power company this when they are billing you though, and you may get a different story). You write. And write. And write.

So while I believe that those dedicated to the idea of writing (rather than being passionate about or prolific with words) can be successful in the industry, I also believe that these people are few and far between in the world of successful writers. If you have the gift of gab though, write all the time, and are ready to break into the industry, then opportunities will open themselves up to you. Read industry newsletters (making sure to read between the lines too), join networking groups, and do lots of research to find the outlets that will suit your style and area of expertise the best. And keep writing. The rest will eventually fall into place.

Here’s a great article/resource to get you started in the world of travel writing.

How much longer will I travel for?

You’ll be the first to know. Your first sign will probably be that this Web Site is either debunked or has been stale for months or years. I believe you can be in one place for a while (as I lived in Australia for a year and a half), and can even return to your home country, and still be traveling. Travel is much more a state of mind, a sense of freedom, and a nature of exploration than it is a definable act. As long as I am still in this world, I am still traveling through it.

How do I decide where to go?

I follow the opportunities. We were on our way to Costa Rica when Kelly (my ex, who traveled with me for the first three years) received a call from his brother in Alberta who was getting married and wanted Kelly in the wedding party. So across Canada we traveled.

Then we were on our way to Costa Rica, when an opportunity to live and work on an ecologically sustainable permaculture educational project in Hawaii nosed its way into our lives. We simply could not turn it down, despite our lack of desire to see Hawaii, which was quite a detour from our travel plans.

After Hawaii, Australia called our names in the form of a sponsored trip with World Nomads. Shortly thereafter a beautiful opportunity to live and work on a fairy-tale-like property near Melbourne lured us in, captivated us, and in turn wooed us into staying in Australia way longer than we had ever expected to stay.

Starting to travel on my own in 2010 was initially a temporary exercise, but turned into a permanent one when Kelly and I went our separate ways. And again it was a fun exercise in planning impromptu travel, and doors continue to open for me…all I have to do is recognize the signs and walk through the doors.

So after having my travel “plans” thrown out the window a handful of times, I now accept that the universe will show me where we are to go next. Everything always falls into place if we allow it to. Hmm….those seem like words to live by – travel-related and otherwise.

How can you do what I’m doing?

This is the biggest question I get. People contact me and say that they love what I do, and ask how they can do it themselves. The question is often as simple as that, rarely with any additional information about the person asking the question.

Before you become the next person in this ever-growing statistic, please think about the nature of your question for just a minute. How exactly am I supposed to answer it?! Not unlike the super-computer in Hitch Hiker’s Guide to the Galaxy, I feel compelled to reply with “42” to this question, as if it is a question about the secret to life, the universe, and everything.

This blog is comprised of lessons learned since I embraced this lifestyle in late 2006 and sold everything I owned. It is an evolving process, as I have made a few mistakes along the way (okay, maybe more than a few), and in turn had my own share of successes. My situation is not what yours will be, nor the next person’s. But there are indeed a few key things anybody can do in embracing the life of a Professional Hobo. I plan to write some targeted e-books to enable more people to achieve this with ease and grace. In the meantime, check out the left-hand sidebar for links to other e-books that I’ve personally found very useful in my own travels. (I get a commission if you click through to them from my site, and there is no price difference for you).

Check out my Travel Tips & Resources page for links to some very useful articles to get you started! 

Do You Want to Write a Guest Post for This Site? 

Please be advised that the only guest posts I accept for this website are for my popular week-in-the-life series, written by fellow long-term and full-time travelers. If you fit the bill and would like to submit a week in your life to me, please contact me and I’ll send you some guidelines.