≡ Menu
Vagabond Journey

How to Enjoy Traveling Long Term

SOSUA, Dominican Republic- Projects and traveling should be synonymous. To do something when traveling that you can build upon with each day that passes — a mission, a purpose, a project — is the first and last steps, in my opinion, to building a full life on the road.

Floating around the world without a tether, occupation, or commitment sounds romantic — and it is for a month or two — but even the greatest of romances often turn stale with age.

SOSUA, Dominican Republic– Projects and traveling should be synonymous. To do something when traveling that you can build upon with each day that passes — a mission, a purpose, a project — is the first and last steps, in my opinion, to building a full life on the road.

Floating around the world without a tether, occupation, or commitment sounds romantic — and it is for a month or two — but even the greatest of romances often turn stale with age.

It is my impression that humans were made to work, that our minds are structured to invite challenges, solve problems, collect, create, and build. My mother told me this when I was growing up, and refused to get a job until the age of 19.

I have always hated work, but I never minded The Work — the projects and little obsessions that can stimulate and command the attention of a man throughout his days. I never wanted to go to work because I was always much too busy doing my own projects to even consider toiling for someone else — I was much too busy for that. Then I realized that if I did not blend my projects with making money that I would need to go home. I was in Connecticut for some odd reason. I got a job.

I helped unload this boat that was full of concrete out of the need for something to do

It is too easy to let your mind go limp and weak when traveling, it is sometimes difficult to find substance behind simply moving from place to place without reason for long durations of time. To travel without a project is to leave out a basic piece of that a human requires to produce happiness.

I look around at the expats in Sosua, Dominican Republic. They are mainly retired, divorced men from the USA, Canada, and Europe. They sit around on the beach, swim in pools, sit in front of the hotel and chat, they drink a lot of beer, get drunk each night, screw “girlfriends.” They are living the dream, they are in paradise, they seem bored to me.

And boredom is little if not a starving for purpose, a show of need for a project.

I read once that alcoholics are often drawn towards the practice out of an urge to enhance the excitement of life, to elevate the pale of ordinary existence, to strive for the extraordinary. I am not sure, I have never had a pathological taste for liquor, but I think a large portion of alcoholism is a result of boredom. Most alcoholics that I have meet seem to have little else to do.

Working on an archaeology project

I am rarely bored because I have filled my life with projects, I always have something to do. I am a person that enjoys the act of doing, of creating, of building, of focusing. I am a pathological concentrator, the rest of the world is a mere background when I am working on a project. I crave this type of concentration. I am an obsessive character that thrives on working on something for the simple joy of being occupied.

If I do a quick survey of the truly non-depressed people that I have known, I think this quality is held in common. In my opinion, boredom is the great purveyor of depression. Only a truly bored person has time to sit around thinking about how much life sucks.

“People need to be productive!” I remember the scolding words of my mother.

But it was a long road before I learned how to blend being productive with traveling. It took many countries and a few continents of travel before I discovered the importance of The Project.

This discovery is what made me a traveler.


I was recently asked in an interview by my friend Dave from The Longest Way Home about the worst day of my traveling life.

I had to think hard about this, I nearly quoted a guy from Cameroon who once turned to me and seriously asked:

“It is true that people have bad days?”

When I answered that it was so, he thought for a moment and then replied:

“I have never had a bad day.”

A bad day of travel is better than the best day of not traveling — as far as I am concerned. My perception on judging bad days is flawed, as I know that even the worse day of traveling is better for me than having a home, a telephone, social obligations, plans, a schedule that must blend flush with other people’s schedules, an alarm clock ringing each morning — I am living the way that I want to, and simply knowing this has the effect of smoothing out many roads that would otherwise be full of bumps and scree.

But I did not want to provide my friend with this stale answer.

So I thought about it. And I realized that I did have a very bad day once. It was the day that I realized that traveling the world could become boring.

The year was 2002, I was in Patagonia. It was my first go at solo long term travel, but my third time in South America. I think I went three months without having a real conversation. My traveling routine then consisted of walking around for around 10 hours a day, eating bread and cheese sandwiches, and writing in a notebook and reading Chatwin by night.

In essence, I had just spent four months doing about nothing. I had no projects, nothing to do each day but walk around, I was building nothing, accomplishing even less, did not work, did not study — I had the entire world before me but no purpose to give it passion.

I realized that I was bored. This was devastating news to a 21 year old kid who had staked out his life for travel. How could I spend a lifetime doing nothing? I needed something, I needed to revived my childhood love of projects but did not yet know how.

“Working makes people happy,” I was haunted by my mother’s words: could she be right?

I was on the verge of discovering that my travels needed to amount to something more than blowing into towns and blowing back out again like the wind — leaving little trace, collecting even less. I got fed up and went home. I left Patagonia.

Though I soon found myself traveling again — to Ireland, to work. I added a new pattern to my travels — they were no longer just for recreation. I began studying. I began choosing topics of interest, going on location, and learning as much about it as I could. This lead me to my international university studies, and out of this the idea of the traveling project was born.

I now had missions behind my travels. I began traveling places to meet people, to study something, to work, and to write about it. I bit into traveling, I stuffed my mouth full of the world, and realized that I was previously just skimming the surface of the art of traveling where I could have dived to the bottom of the jug.

Traveler studying in Thailand

I began Vagabond Journey.com out of one of my university projects, and this has been the deep dark hole of a project that I have been diving into ever since. Without Vagabond Journey.com there is a good chance that I would not still be traveling. I briefly discussed the possibility of closing shop on the website with my wife a couple of days ago. It was not a serious conversation, I just wanted to see what she would say.

Publishing this site takes a lot of time — I work a full time job like everybody else. I wanted to see if my wife would rejoice if I packed it in and spent my all-day-longs with her and Petra.

She looked at me sharply and quickly stated, “There would be no reason for us to travel anymore if you did that. Just going from place to place gets boring.”

My wife is into the project too.

Chaya’s assessment was acute, it was accurate, she is a person who understands long term travel: traveling around the world for years on end without purpose is a curse — listlessness is the hallmark of a displaced person, Cain’s punishment was to drift about the earth aimlessly. Long term travel without a purpose, a mission, a project can quickly feel like exile. It gets real repetitive just going around the world buying things and having the same inane conversations each day. It is my impression that travelers need projects.

Please believe me, if you are an aspiring traveler with limited monetary resources the routine of travel can get pretty boring pretty quick. Just how many times can you get on a bus, get off a bus, walk to a hotel, stash your bag, walk around, eat in a restaurant, go back to the hotel, leave again, drink a beer at a bar, get asked where you are from, go back to the hotel, go to sleep, wake up, get on a bus, go to another town . . .

A month of this is exciting, two months is to get a thorough routine down pact, anymore and I begin to feel sallow, frail, and weak in the body and in the head. In Patagonia I was feigning for stimulation, I needed to put my idle hands to use, I needed a project. But I did not know this at the time — I thought there was something wrong with me — and I went home.

The less the likelihood of coming out of the other side of a project, the bigger the mountain, the less chance you have of bringing a project to completion the better. I can never complete Vagabond Journey.com. It is too endless, the plot is the entire globe and everything in it. I can take up an interest in virtually anything and it will fit into the theme of this project.

This website has been the fuel, the impetus behind my travels for the past three years. Before this I mixed university projects with archaeology fieldwork. Each day I wake up with a project I have something to do. Each day I can build a little upon that which I did the day before. Each day there is something to accomplish.

Working as a gardener

Every night I go to bed I think for a moment about what I did during the day, I count the pages that I published, I think of travelogue entries that I completed, the travel questions I answered, and I take a quick look at where I stand. This feels good.

I am happy with my days because I work, because I found something to do while traveling. I don’t just make this website because I travel, but I also travel because I make this website. The two endeavors go hand in hand, they are now inseparable, they run flush together: they are the same project.

A working definition of a project

A project is a deep dark bottomless hole that men and women jump down into for the purpose of providing themselves with challenges, stimulation, a purpose, a modus-operadi, a jest at productivity. Projects provide a sense of accomplishment, they can tangibly show the time of your life that you put into them. A project is a monument to yourself: I put X amount of my life’s duration into this thing and here it is. Projects are monuments to your life.

I think of the guy who is building a mountain out of hay bails in the southwest of the USA. He says that he is doing if for God, and it is my impression that he is on to something. The actualization of time spent is often an actualization of life itself.

There are many projects that I think would mold themselves very well with traveling. There is writing, website construction, working jobs, teaching English, taking classes, learning a trade, being taught how to dance, studying a foreign language, practicing an art, self-conditioning your body, climbing mountains, becoming a dive master, volunteering on farms, trading work in hostels for free accommodation, collecting stories, collecting things, studying abroad, investigating history, learning about culture.

The possibilities are endless.

I am often asked by readers what they need to do to prepare for traveling, and, beyond the basics, the best advice I can give them is to find a mission, find something that you are passionate about, something that you are interested in, and discover a way to weave it into your travels, find a project.

Filed under: Perpetual Travel, Travel Philosophy, Travel Tips

About the Author:

Wade Shepard is the founder and editor of Vagabond Journey. He has been traveling the world since 1999, through 87 countries. He is the author of the book, Ghost Cities of China, and contributes to Forbes, The Diplomat, the South China Morning Post, and other publications. has written 3348 posts on Vagabond Journey. Contact the author.

Support Wade Shepard’s writing on this blog (please help):

Wade Shepard is currently in: Prague, Czech RepublicMap