Tips for Independent Travel Business

BY Wade Shepard TIMENovember 14, 2014 PRINT

Original article on

A few months ago I began a series on independent travel businesses, and I went around and interviewed travelers who earn their own keep through running subsistence level micro-businesses. For this series, I interviewed traveling musicians, a tattoo artist, a mobile baker, an SEO consultant, a wandering shoe maker, a freelance writer, a vagabond massage therapist, a perpetually traveling jeweler, a troupe of fire dancers, and a sailor who sells hand made soaps in the street.

Through conducting these interviews and peering into how other travelers are making a living, a collection of attributes rosed to the surface that most of these businesses had in common. From this, I was able to come up with a recipe for what makes a successful independent travel business.

How to be successful with an independent travel business

Believe in Yourself to the Point of Disillusionment

Few successful ingenuitive people way by doing what other people felt made sense, they did not follow the laid out road before them. In terms of running an independent travel business, this means not letting a lack of examples to emulate hold you back. Truly live your own fantasy, step out into the world and do what you imagine yourself doing.

There is only one way to test if an idea is good or not: try it. If you get the notion to sell something in the street in a certain place, try it. If you think you can make a living yodeling in metro stops then yodel away. If you have an assumption that people may want to buy your art, eat your cookies, or listen to your music then put it all out there. If there is a potential that you can make a living off of an idea, then there should be nothing that stops you from trying. Sometimes, you will find that there is a reason that other people are not already doing what you propose, other times you will strike up a way to earn your keep on the road.

The laid out road of travel says that you should seek formal employment, work, then travel when your job is over. Few people attempt to make money daily on the road. For many, the idea of working and traveling are mutually exclusive; for most, the discipline to work for independently is not strong enough. Running a successful independent travel business means working daily, it means staying in when others are out playing, it means transitioning the idea of travel from a recreation activity to a full fledged lifestyle.

A Business That Will Work in Your Location and With Your Present Means

If you are living in a rain forest hostel and do not have access to an oven then trying to start up a baking business is probably not going to work. An independent travel business must suit the environment where you are traveling as well as your available means. Location is a paramount consideration when figuring out a way to make money on the road, and many travelers who run independent travel businesses make their money in areas where other tourists frequent. You can try to sell macrame butterflies in the hills of Laos, but I am unsure how many sales you are actually going to make.

Some considerations to reconcile about finding a location for an independent travel business

  • Is there a customer base/ audience for what you are selling or providing?> If nobody wants your stuff, there is no point in trying to sell it to them.
  • Is it legal, or at least acceptable, to run your business where you intend to set up? In some places the streets are a free for all for the independent economy, in others there is no such thing.
  • Is there a lot of competition with people involved in similar ventures? If you are selling macrame butterflies it might not make any sense to sit in a row of twenty other macrame butterfly sellers. Either make something different to sell or split to another location.
  • How long do you want to be in the places you would need to be in order to do a particular business? How long is it going to take you to establish your micro-business in a particular place? Do you really want/ are set up to stay there that long?
  • Do you have what you need to run your business where you are, do you have access to a proper set up? Do you have access to everything you need to run your business, or are there some essential elements missing?
  • Can you afford to run your business where you intend to set up? In point, trying to make up a $40 per night dorm bed bill by dancing in the streets may be a potentially frustrating venture.

There are vastly more parameters for running an independent travel business that involves the selling of items and services in person than those that are internet based. For an internet based business, the only real parameter you have is internet access, and, fortunately for us, each day brings more places from which we can work. But for the traveling artisans, musicians, and street vendors location is of paramount importance.

In Central America and Mexico there is a circuit that the traveling musicians and artisans tend to follow. They go between the towns that are known for being good for their particular business in a very predictable route. Find the circuit for your particular occupation, and engineer ways to make the most of it.

Do Something You Are Good at and Like Doing

It is silly to try to be a traveling artist if you suck at art. Not everyone needs to fund their travels making macrame butterflies. If you can’t play an instrument, do you really think you can learn how to do so well before you go broke? Find something that you like to do and are good at and then come up with ways to make money from it.

Tenacity to Take This Idea and Make It Reality

Almost every traveler that I interviewed for this series were very tenacious individuals. Most of them were not people who were born to work for themselves, seriously not people to take orders from another. Many of these characters choose to live poor and make only a fraction of what they otherwise could just for the pleasure of being their own boss. This determination lead many of them to make something out of nothing in their micro-businesses.


Rebbecca, the freelance writer who I interviewed for this series, is a gregarious person. She engages friends and potential friends with open arms, she is a good talker, her travel business thrives. While, on the other hand, many other travelers are not this successful. I saw a girl (European?) in the street the other day selling tweed sandals that she was making. She was wearing a rotten face. It was so rotten, in fact, that I walked by her as quick as I could, I did not even want to speak with her long enough for an interview, save buying her hippy sandals.

In many aspects, gregariousness = success in travel. If you go out in the world, speak with people, ask questions, and show an interest in people doors will open before you. Captain Jim is a fantastic talker, and he sells ten times more merchandise per night than any of the hippies acting coolly aloof behind their jewelry stalls. Gregariousness is essential for making the most of an independent travel business that requires face to face communication.

Have Confidence

If you are not a naturally confident person, pretend you are. A course in acting should be part of any traveler’s preparation. Even if you are a quivering little peon, when running an independent travel business acting like the alpha male will only work to your benefit. People with confidence draws other people in, confidence is something that people are attracted to — like fish to a lure. Reel them in, go into your business with your head up.

There was not one traveler that I interviewed for this series who was not overwhelmingly, observably confident. It takes balls to go out in a foreign country and try to make a living, it is something that requires confidence, it is something that creates confidence.

Enjoyable Success

In point, success means nothing if it is not fun — if you don’t enjoy your independent travel business, no matter how much money you make it will not be worth it. Many readers have suggested excellent ways for me to make a lot of money when traveling, I know of dozens of strategies that would bring me in many times the amount of money that I make working on, but I know that I would not enjoy them as much.

The game here is not just to make money, but to enjoy making money. Both criteria need to be satisfied equally here for an independent travel business to be called a success.

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Copyright © 2014 by Vagabond Journey Travel. This article was written by Wade Shepard and originally published on

Wade Shepard
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