Our next guest for Free Spirits Friday is none other than Derek from Wandering Earl. Wait, what? Shouldn’t it be Wandering Derek then? Well, according to the man himself, Wandering Derek just didn’t have a nice ring to it. So he went with his middle name for his travel blog.

The man behind Wandering Earl has visited over 100 countries, he’s been kidnapped, he’s acted in a Bollywood movie, he’s worked on cruise ships and he’s taught English in Thailand. Most impressive of all: ever since Christmas Day 1999, Earl has been travelling non-stop. That’s right.

I think it’s safe to say that this guy has a lot of expertise on living a travel lifestyle and working as a digital nomad. This is the story of Wandering Earl.

Introduce yourself to us and talk us through how you became a nomadic world traveller.

Back in 1999, after graduating from university, I decided to take a 3 month trip to Southeast Asia before starting my career as a sports agent. I took off on Christmas Day and flew to Bangkok. I then celebrated the Millennium in Cambodia. And that night, I decided that 3 months wasn’t going to be enough at all. I had to find a way to travel for a much longer period of time. Of course, I imagined that a ‘longer period of time’ might mean 1 or maybe 2 years if I was lucky. After all, I only had $1500 to my name at the time. However, here we are and that trip has still yet to end. Since 1999, I’ve been on the road non-stop, traveling to over 105 countries. I’ve been figuring it all out as I went along. Since 2009 I’ve been blogging and in 2012 I started my own tour company, Wandering Earl Tours. I manage both of these from my laptop wherever I happen to be traveling. So, travel has honestly become my life now that it’s been almost 20 years, so much more than what I had originally envisioned!

How come you never came back home from your post-graduation trip to Southeast Asia?

Two things made it impossible to go back – people and education. The simple fact that I was meeting so many new people that I otherwise would never have come across in my life, hearing their stories, learning from their experiences and creating incredibly strong bonds was probably enough to keep me going. But when I thought about the overall education I was receiving from every place I visited, every meal I ate, every village I passed through and every interaction I had, I absolutely could not imagine life without these two things. And that was it. Right there at Angkor Wat, I was celebrating the Millennium and pondering what I had already been through in such a short period of time. And I realized that I had to keep traveling as long as I could. I didn’t have a plan, I didn’t know anyone who was out there traveling the world. I didn’t know where this would all lead. But I didn’t care. I felt it deep inside that this was a decision I needed to make.

How did you afford to travel after your initial budget had been run down?

This was a little tricky at first as my money was dwindling quickly. I only had $1500 when I set out. And now that I planned to travel indefinitely, I obviously needed some source of income. It all came down to talking to as many people as I could, both locals and other travelers alike. I was trying to figure out some ideas that could earn me some money. Back then I couldn’t just go online and find endless ideas. It didn’t exist. So, at one point, I met another traveler who told me to go to Chiang Mai, Thailand and teach English. Eventually, that’s what I did. I posted hand-written signs around the Chiang Mai University campus, along with a friend of mine who joined me. The signs said ‘Native English Speakers willing to teach English’. We received about 100 calls within the first week. Before we knew it, we had daily classes lined up where we would sit in the park or in a cafe with a handful of students and teach them English. From there, I met another traveler who mentioned working on board cruise ships. About 1.5 years later, when the money was low again, I took his advice. I ended up getting a job as a Tour Manager on board a cruise ship. This allowed me to save some money, continue traveling and eventually, give me the opportunity to start working online.

What’s the most surprising country you have visited?

Probably Syria. I visited Syria about a year before the current fighting broke out. It turned out to be one of the most rewarding travel experiences of my life. I had no idea what to expect at the time but I certainly didn’t expect such beautiful cities (especially Damascus and Aleppo), such stunning sites (Palmyra, Krak des Chevalier Crusader Castle, Maaloula Monastery), vibrant markets and wonderful food. To top it off, I have never been invited into more homes, to more local events or to more local celebrations than in Syria. Everyone was incredibly welcoming, the entire country felt so safe and nobody tried to rip me off or cause problems. Everywhere I went, I made local friends in a matter of minutes. My original plan was to stay for 2 weeks but I ended up spending 6 weeks inside the country in the end!

Is visiting every country on earth on your bucket list?

Nope. For me, the main reason I travel is for the interaction with all kinds of people. If I was just looking to check off countries from a list or see the main sights, I would have stopped traveling a long time ago. So, with a focus on interaction, the actual destinations don’t matter as much. Sure, I’d like to see as much of the world as I can. But still, seeing every country on the planet is not a goal.

Do you still stay in $1 dorm rooms? Do you still feel it’s worth compromising on your health and quality of sleep to save some money?

These days I no longer stay in such dorm rooms. But yes, I feel it’s definitely worth it. It’s something that I feel all travelers should experience at some point. Forget about the health and quality of sleep aspects. It’s not going to have much of a long-term effect if you stay in $1 dorm rooms for a year. However, spending so little, sharing a room with strangers, learning to live very simply and not being comfortable all the time – those all provide lessons that will definitely have a long-term (and positive) effect on one’s life. My days of staying in such dorm rooms absolutely helped shape who I am. They taught me a great deal about interacting with people and surviving with much less than I ever thought I could survive with. Of course, you don’t need to sleep in such places for years on end. However, going beyond your comfort zone and trying it out for a while will definitely lead to great, long-lasting benefits.

Do you ever get burnt out on the road, longing to go back home?

First, yes. I do get somewhat burnt out from time to time. But I don’t have any kind of longing feeling to go back to the USA to live a more settled life. Also, since I really don’t have a home to go back to, that’s a bit difficult. My family and old friends are all scattered around the US, my girlfriend is from Romania and some of her family lives in Sweden and we have friends all over the world. So it’s difficult to pick a place to call home. However, when we do get burnt out, which definitely happens with all the moving around, we simply pick a place that we know or think we’ll enjoy and we stay put for a while. Maybe it’s a month like our recent stint in Lisbon. Maybe it’s 2 or 3 months if that’s what we need. It’s definitely important for us to rest and just be in one place whenever travel starts to overwhelm us or maybe we need to concentrate on work more than usual. Our set up allows us to do that. And once we’re ready to get back on the road, off we go. For us, this works perfectly.

How did the idea of starting a touring company occur to you?

In 2012, readers of my blog, Wandering Earl, started asking if they could travel with me. I would get emails such as “Hey Earl, I know you travel to India a lot and I’d love to join you the next time you go!”. So, it got me thinking. If so many people are interested in traveling with me, maybe I could organize a group trip so that everyone can join at once. That’s how it all started. I put together an India itinerary and announced it on my blog and social media. The trip sold out in less than 24 hours. A few months later I added a Mexico trip and then another India adventure and they sold out as well. Before I knew it, I was offering more and more trips every year, to more and more countries around the world.

How do you decide which destinations to cover with Wandering Earl Tours?

When I started, all of the destinations were based on countries that I had been to many times and that I knew extremely well. This included India, Mexico, Romania, Thailand, Cambodia and Turkey. And for the most part, that’s still how I choose the countries for the tours today. However, I also listen to requests from my readers as they are often suggesting certain countries where they would love for me to organize a tour. If it happens to be a country I’m not too familiar with, I simply start getting familiar with it. In the end, whether it’s to a country I’ve been to 30 times or 2 times, it’s the laid-back, small group style of these trips that really appeals to those who join.

What attracts you so much about the nomadic lifestyle that a ‘normal’ life can’t give you?

It’s all about freedom. The freedom to wake up each day and decide where I want to go or what I want to do or how I want to live. I personally love travel so this freedom enables me to be nomadic and travel as I wish, to interact with all kinds of people, to never stop learning, to partake in activities that otherwise would only remain a dream. This kind of control over our lives simply isn’t possible with a more ‘normal’ set up. Once you have a taste of such freedom, it’s very difficult to give up of course.

Thank you so much to Derek for taking the time to answer these questions and to give you all some insight into the world of a digital nomad. You can follow him on his blog Wandering Earl, on Facebook, on Instagram and on Twitter. You can also check out his tour company on Wandering Earl Tours.