So You Want to Travel the World? Here’s Where to Actually Start

Photo Credit: Jean Carlo Emer

People frequently ask me how to travel the world. Friends, in particular, who are interested in traveling the world will approach me curious about how to best do it. There are a lot of logistics to consider. In this article, I will focus on one of the first and most central questions someone thinking about traveling the world tends to have: “I want to travel the world, but I don’t know where to start. What would it look like to take some first steps towards traveling without upending my life as it is right now?”

For anyone considering traveling the world, my first recommendation is to test it out in phases. Take a month or two long trip to see whether you like traveling. Go somewhere you’d find interesting. Then take a five or six month-long trip. And if you still enjoy traveling after that, then and only then try traveling as a full-time lifestyle.

Don’t sell everything and go. It is smart to test the waters while still retaining some ability to go back and resume a normal life if you conclude you do not like it. For example, if you can, during the first month trip, keep your apartment or home back home and your job, so that if you learn that you do not enjoy it, you still have a life to go back to. You can increasingly disconnect from your home environment little by little after each trip. World travelers commonly sell or otherwise give away most of their possessions, traveling with only a few bags. This makes sense for years-long trips, but it may be best to test the waters with trips of increasing lengths before taking such a life altering action.

Traveling long-term is the type of activity where you have to do it in order to learn whether it works for you. (And to be clear, it doesn’t work everyone; despite being many people’s dream, I think the traveling lifestyle doesn’t work for most people.) Most people’s experience with travel are short vacations for at most a few weeks, which can be a lot of fun but are totally different from long-term travel.

In life, we accrue a lot of different types of experiences, which we can use to get a sense of what to expect when we have an upcoming experience. For example, if I decide to take a course at a university, I have attended courses before. School is something I have done for many years of my life, several decades even. Even if this class may be unique in all sorts of ways, I have some reference point for what class is like and how to get by in that environment. That is not the case with long-term travel. Short-term vacations are very different and do not make a good reference point. Thus, we need to learn about what the experience is like. Testing it with a few shorter trips of a few months is the most effective way to do that.

Each person has a slightly different set of logistical questions to sort through when figuring out to go on these shorter trips. Usually, I recommend you pick a country or region of the world they you always been interested in visiting. For some friends I have spoken with they had always wanted to visit the Caribbean; others Asia; others South America. Wherever that is for you, use that.

The more complicated question is how to maintain enough ties with your previous life that you can return to it with minimal stress if you learn you do not like traveling. The most common work ways to maintain a connection to work that I have seen are to:

  1. Negotiate to work remotely for a month or two while traveling
  2. Opt to take a month or couple-month long break from work, where if needed, they can return to their job.
  3. Others are already in between jobs and decided to travel for a few months to unwind from the stress of whatever they just went through and rediscover themselves.

For your home, most people who rent will keep their apartments, if they can afford to continue paying their rent while away. Obviously anyone on a mortgage will likely still have to pay their monthly dues while away. Many have family they can move back in with if need be to return home in a pinch. These will not work for everyone, but they are the most common strategies I have seen.

You can both determine whether they rhythm of traveling works for you, in many cases figuring out the exact style or approaches that work best for you. It’s a practice run. Everyone has key personal questions they have to work through if they decided to travel permanently, such as how to juggle work while traveling or how to navigate relationships with loved ones back home. On a couple month-long trip, you will naturally encounter these issues and learn about how you deal with them, and you will have to determine the techniques that work best for you to deal with them. Most world travelers realize that they are capable of dealing with it and have developed the skills to do so that they can use on a longer trip. If your issues prove insurmountable during those months of travel, you just learned that travel is not for you. Worst case scenario, you just return back home with what will still likely be some kind of life-changing experience.