Welcome to the first edition of our Traveler Interview series! For this one, we reached out to someone who’s been a huge inspiration to thousands out there in the digital and travel universe, including us: Wandering Earl.

He’s been at it for fifteen years, blogging for five, and getting himself into all sorts of great experiences that help everyone realize that anyone can travel, and that a life of doing so can be a reality.

From working on cruise ships, to volunteering, being put in dangerous situations, working on cruise ships, teaching English, running a tour company, and, of course, being a full-time blogger, he’s got the experience and the know-how to lend an endless array of advice to all you folks out there who want to do your own thing.

And with that, let’s get started.

1. How long ago did you begin traveling, and what made you start?

I started back in 1999 when I took a three-month trip to Southeast Asia as a university graduation gift to myself. My plan was to spend the $1500 I had to my name, and then return home after the three months to begin my career. But, somehow, that never happened. About ten days into that trip, while celebrating the Millennium at Angkor Wat in Cambodia, I decided that I wanted to try to figure out a way to turn travel into an actual, sustainable lifestyle. So, I didn’t get on my return flight and I took it all one step at a time…fifteen years later, the journey still continues.

2. Do you consider yourself a traveler, an expat, an explorer, or something else, and why?

I’ve never been a big fan of categories because using a particular word always comes with such general stereotypes and associations. I’m just me, living my simple life, which happens to involve a good amount of travel.

3. Where are you from, where are you now, and where are you going next?

I’m originally from a town outside of Boston in the U.S. At the moment, I’m visiting family in Florida, and over the next few months, I’ll be in Romania, Turkey, India, Morocco, and if all goes well, Japan, too.

4. How do you find living expenses to be, compared to your home country?

For the past three years, my base was in Bucharest, Romania, where you can live well for less than $1000 USD per month. This would include renting an apartment, using taxis and public transportation, eating out a decent amount, going out at night, etc. You have everything you need or would have in North America and Western Europe at a fraction of the cost, which is why many people who work online are heading to Romania to live for a while.

5. Where was your first big travel stop? How and why did you choose that to be the first one? How long did you stay?

My first trip was to Southeast Asia as mentioned above, specifically to Thailand, Cambodia, Vietnam, and Laos. I chose this region because I had spent a year studying abroad in Melbourne, Australia, while at university, and during that time, I learned a great deal about these countries simply due to Australia’s proximity to the region.

Before this experience, I really knew nothing about SE Asia; but the more I learned, the more curious I became. So, I knew that as soon as I would have a chance to travel after graduating university, this was the part of the world I wanted to visit. On Christmas Day, 1999, I followed through with that plan when I flew from the U.S. to Bangkok. And of course, I spent far more than the three months I originally planned to stay.

Krak de Chevalier, Syria by Wandering Earl

6. What’s the average amount of time you spend in one place?

It really depends for me, since I will visit some countries specifically to travel, and other countries to concentrate on work, and not move around too much. As a result, I could stay anywhere from one week to three months in one place. In general, I prefer slow travel, so I do like to stick around each destination for as long as I can. Sometimes that’s possible; but other times, due to many reasons, it has to be a shorter trip.

7. Are you a planner, or do you tend to fly by the seat of your pants?

Definitely not a planner. Apart from learning how to get from the airport into the city center and perhaps booking my first few nights of accommodation, I barely plan anything at all. I prefer to just arrive and see how the adventure unfolds, without having many expectations.

8. What do you do for a living, and is travel an integral part of it?

I’m a travel blogger, and I also work on several other online projects and companies. Travel is definitely a major part of it all, as without constant travel, my blog probably wouldn’t exist and my other projects, such as leading tours, writing eBooks, creating a travel start-up (Plansify.com), etc., also would not hold much weight if I wasn’t actually living the lifestyle that these projects are based upon.

9. Do you think you made the right choice overall by leaving behind the typical life in your homeland?

Yes, I’m very happy that I made this choice. I wouldn’t have wanted it any other way. As soon as I had the idea, back in 1999, that I wanted to try and turn travel into an actual lifestyle, I knew that this decision was going to be the best decision I had ever made. But at the same time, I also knew that if I ever changed my mind and wanted to try out a more typical life at some point, I could always change. So, I don’t feel as if I left anything behind. I just chose a different path that has taken me on a 15-year adventure so far…where it shall lead me in the future, I have no idea!

10. How do you think your life has changed for better or worse since you left for your adventure?

If my life hadn’t changed for the better as a result of all this traveling, I would have stopped traveling a long time ago! For me, it’s all about meeting people and the education that such cross-cultural interaction provides. It’s really that straightforward. And, it’s that education that has helped me grow as a person, helped me gain a more mature perspective on the world, and has really provided me with the foundation for all of the projects I work on, goals that I want to achieve, and values that I live by.

11. Do you still feel a connection to your old home, or did you really leave it all behind?

I still feel a connection, even after 15 years of travel. Maybe not to Boston or my actual hometown – since most of my family and good friends have moved away – but definitely to the U.S. I think a major part of who we are comes from our youth of course and as a result, the connection that is built during those years, to our friends, to our education, to all of the life-shaping experiences we have, will never vanish. Consequently, that connection to my home country won’t vanish either since that is where I grew up and where my life began to take shape.

12. Do you go back often, and do people come visit you while you’re on the road?

These days, I return to the U.S. about three times per year. In my earlier days of travel, it was more like once per year. At the same time, my family and friends do visit me in various places throughout the year as well. It works out perfectly for them; whenever they have some vacation time, they just ask me where I’ll be and then they tell me they’re coming to visit. They don’t have to plan anything, I take care of that part and I get to spend time with friends and family in different destinations.

13. Is there anything you miss from your home country that you can’t find when you’re traveling? If so, what is it, and how do you manage to get your hands on it while you’re on the road?

Good Mexican food. Outside of Mexico and the U.S., it is hard to find. And there’s really nothing I can do about it, unfortunately, except wait until I travel back home, where the first meal I almost always have involves some enchiladas or chilaquiles or tostadas. Apart from that, not much else. I’m quite an easygoing person, so I don’t really miss too much, and I can adjust quite easily to any situation or destination without really needing something that might not be available.

14. How is the language barrier for you when you go somewhere new, and do you make an effort to learn the local tongue?

I’ll always say that there has never been a situation during my 15 years of travel where I was completely stuck and unable to communicate with someone. Through basic English, a few words of the local language, body movements, and facial expressions, you can always get your point across; and besides, English is spoken in almost every corner of the world these days.

Of course, learning some of the local language definitely helps, and I do always try to learn as much as I can. I think it’s very important to show people that you are genuinely interested in learning about their country and culture, and one of the best ways to show this is by speaking some of their language.

Amed, Bali by Wandering Earl

15. What has been the biggest challenge for you? Bureaucracy? Finding new friends? Something else?

I think the challenges have changed over the years, from missing family and friends at the start, to living out of a backpack and always packing and unpacking and sleeping in new places all the time, which can become quite exhausting; and more recently, to figuring out how to divide my time between work and travel, so that I am able to work efficiently and also make the most out of my travel experiences.

Trying to work while traveling is nearly impossible if you really want to progress with any project, so I now alternate between periods of travel and periods where I stay in one place to really focus on work. Otherwise, it’s quite a mental struggle, because without some stability and routine, it’s easy to become lazy, or sloppy, or just too tired to get any real work done.

16. How hard is it to make friends and have a social life? Do you ever feel alone?

I actually think it takes more of an effort to spend time alone than it does to have a social life while traveling. There are always people to meet – with so many ways to meet both locals and other travelers these days – and as a result, I always find myself having more than enough social opportunities. Rarely do I feel alone, and when I am alone, it’s most likely because I just need some time to myself and I have made the decision to do so.

But, if any traveler ever feels alone while traveling, all you need to do is book a bed or room at the most popular hostel in town, or jump on couchsurfing.org and meet up with some locals for coffee, and before you know it, you’ll be having quite a social life wherever you happen to be.

17. If you could change something about how and when you became a traveler, what would it be?

I would change very little, if anything at all. The only thing I can think of is that, in my earlier years, I wish I had more of a purpose to my travels. At the time, I was simply traveling for the sake of traveling, mainly to just see the sights and meet some new people. But, I wish that I had more specific goals, specific things I really wanted to learn and work on in each destination, instead of just seeing how long I could make my money last and how many cool places I could visit. It’s all a learning process, though, and I still wouldn’t trade those early days for anything else; but, having that purpose would have helped give my travels a better structure to build upon from the start.

18. Do you think it’s easier or harder to become a hardcore world traveler today, versus when you started?

Probably easier, just because you can jump online and in twenty minutes find endless examples of people already living this lifestyle. And in the end, that’s really what you need, because the main reason people don’t go after this kind of life goal is because they are not confident in their ability to make it happen, or they are worried about leaving a more typical lifestyle behind. But, once you see endless examples of others who have made the leap successfully, suddenly your confidence boosts and you find the inspiration to get out there yourself.

Back when I started, there wasn’t much online, so you really had to just take the plunge, quite blindly, if you wanted to travel long-term, and just hope that there were opportunities out there that would help you achieve your goal. I hadn’t known about any long-term travelers at all when I decided to try and become one. It was much more difficult to find real examples.

19. What crazy story can you tell us about a terrible travel experience, and what, if anything, did you learn from it?

For three days, I was kidnapped by a gang of taxi drivers in Dhaka, Bangladesh. It all started when I walked out of the airport after midnight, chose a taxi driver to take me to a specific guesthouse, and then found myself locked in a taxi with five random people. In short, over those three days, they kept me locked up in a couple of different buildings in the slums of Dhaka, and would try to get me to take out money from the ATM machines around the city. Of course, I would just type in the wrong PIN number and tell them my card didn’t work.

They weren’t violent or armed, and definitely weren’t the brightest kidnappers in the world either, so after the first day, I wasn’t too nervous. Luckily, on the third day, they told me to go up to my room and grab my backpack (which they never took from me), because they were going to move me to a different place. On my way downstairs, I noticed a hallway with an emergency exit at the end, and so I just ran to the door, down the outside stairs, and I then took a rickshaw to the guesthouse I originally wanted to go to three days prior.

What did I learn? Always stay calm, even when you find yourself in a tough situation. Getting angry or upset, especially when in a foreign country with an unfamiliar culture, does not help at all. Staying as calm as possible will ensure you maintain a clear head and as a result, make better decisions without putting yourself in a worse situation or at increased risk. With that said, it is important to note that these kind of situations are extremely rare and definitely not something for any traveler to really worry about!

20. What about a good experience you had that makes it all worthwhile?

These kind of experiences happen all the time! There was the random village of Tamga, Kyrgyzstan, that I stumbled upon and which ended up being the highlight of my visit to this country, simply because of the amazing woman who owned the only guesthouse in town. Tamga is the kind of place where, when I walked off the bus in the seemingly deserted center of town, I thought I might stick around for a few hours and move on.

But, after finding the guesthouse, the owner immediately treated me as family, gave me such insight into the local culture, and basically wouldn’t let me leave…and I didn’t want to leave, either. It was crazy how quickly I went from wanting to leave the town to wanting to stay for a long, long time, and how one local interaction can lead to such a change.

There are also road trips around Romania with new friends, being invited to a local wedding in Yemen, hiking around the Karaokaram Mountains in Pakistan, eating lunch with locals in a random Mexican town, spending New Year’s in a different country each year with different people…and on and on and on.

Transfagarasan by Wandering Earl

21. Do you have any favorite places that will always bring you back, or that hold special memories for you?

Socotra Island, Yemen. Few people have heard of it, almost nobody has visited, and to me, visiting this island in the Indian Ocean was one of the most special experiences of my traveling years. It’s a destination that needs to be seen to be believed, and is often called ‘the Galapagos on steroids’ for its surreal landscapes and plant life. The local people are also very laid-back and friendly, most of whom never leave their isolated island. Again, it needs to be seen to be believed, and I will never forget the time I spent there.

22. What about places that are nothing but a turn-off, regardless of whether you have visited them before or not?

None really come to mind. My theory is that I travel to meet people, and as a result, there are new people to meet in every country in the world. So, I’d be happy if you dropped me anywhere. With that said, for some reason, China is at the very bottom of my list of places I have a strong desire to visit. Nothing against the country, and I have been once already on a very short visit to Beijing, but it just doesn’t interest me as much as other destinations. Some country has to be at the bottom of the list, I guess.

23. What dos and don’ts can you offer a burgeoning traveler?

In the ‘dos’ category, new travelers should do their best to stay flexible and keep their options open by not trying to plan every detail of their travels in advance. It is important to realize that, as soon as you start traveling, you’re going to meet new people and learn about new destinations and opportunities, and before you know it, you’ll be off in new directions that you never even imagined. But, if you’re not flexible and open to such changes, it will be very difficult to take advantage of everything that travel can offer.

As for ‘don’ts’, I would say not to worry too much. The world is much safer than you probably imagine, and if you use the same common sense you use at home, the chances of anything happening while traveling is equally as low. Again, just search for examples of people who have been traveling for a long time, and I’m certain the chances of them telling you that something really bad has happened to them while on the road are quite slim.

24. Would you recommend people follow your path?

Actually, I would recommend that people create their own path, using other travelers’ paths as inspiration. Following someone else’s path is not a great idea, because we are all different, with different interests, skills, needs, etc.; and so, there is no way that two people will have the same success with the exact same path.

But, the key to creating this lifestyle is remembering that there are infinite ways to make it happen, and that everyone who is traveling long-term has indeed made it happen in their own way. This is great news, of course, because it means that anyone else out there who is interested in such travel has a very good chance of achieving their goal, as long as they are determined enough to take the first step.

25. Do you think you’ll ever stop traveling and settle down somewhere?

I really have no idea. If I were to wake up tomorrow and suddenly reach the conclusion that it’s time to stop traveling, then I’d stop. But, until that happens, if I continue waking up each day still wanting to maintain this traveling lifestyle, then that’s what I’ll continue doing!

26. In a parallel universe, what would be your ideal lifestyle, and why?

Probably something where my work would involve using my hands, such as farming or building things, where I would live more closely to nature and not spend so much time in front of a computer. That’s one of the major downsides to my current work: way too much time on my laptop. I really am trying to restructure my work so that I can spend more time offline these days.

27. If you could be a beverage, what would you be, and why?

Fresh watermelon juice. It’s simple and doesn’t draw much attention, but you can always rely on it to provide you with a cool, refreshing experience.

28. Any last words of wisdom or warning?

If you start to lose confidence in your ability to achieve long-term travel, don’t be afraid to actually contact those who are out there traveling right now. Reach out to them, ask them questions, and before long, you’ll find that their own travel stories, their own advice on how to overcome the challenges, their own tales of how they were once in the exact same situation as you are in, will suddenly help you gain all the confidence you need to get out there on the road yourself.

And, when it comes to achieving long-term travel, what’s far more important than having money or any particular skills is having a combination of determination, a willingness to be creative, and an ability to network with as many people as you possibly can. Also, the fact that almost nobody regrets having traveled, no matter where they went, for how long or even how it turned out, should be enough to convince anyone who wants to travel to at least give it a try.

Socotra Island, Yemen by Wandering Earl

And that’s a wrap! Thanks so much to Wandering Earl for giving us the time and answering our questions. Hopefully, he’s been a source of information and inspiration for you as you follow your own path. You can visit and follow him at the following locations:

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