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July 17, 2013 / A Mindful Traveler

An Interview with Wandering Earl

Wandering Earl

A nomad since before the turn of the milennium,  Derek “Wandering Earl” Baron is quite simply a legend within both the blogging and digital nomad communities.  If you’re unfamiliar with his story, I recommend taking a moment to read it in his words.  His most recent post, likening life to hiking in Romania, where he’s currently based, offers another window into his philosophy, as well as his interest in mindfulness.  He’s well known for answering every question about travel he receives and was kind enough to answer mine about his life, travels, and interest in vipassana meditation.

Many people are aware of the inspiring storyof how you realized you wanted to be a permanent traveler, but at what point did you realize you’d succeeded in sustainably “living a life of travel”?
I would say the first time I made that realization was when I was working on board cruise ships back in 2006. Up until that point I had really been trying to piece things together and I really had no foundation that I could rely on to create the lifestyle I wanted. But suddenly, I realized that working on board cruise ships offered me an opportunity to really save money for as much traveling as I wanted to do in between contracts. In addition, I had landed a good position (Tour Manager) that also provided me with valuable work and life experiences while allowing me to network with people from all over the world. And this is when it all came together…  I was making contacts, saving money and no longer struggling to find a way to pay for my next round of travels. I also realized that I could work on ships for as long as I wanted or I could take some of the money I was saving and use that as a cushion to create a new work/income opportunity that I could do while traveling. From this point on I was no longer worried as I knew that turning travel into a lifestyle was more than possible.
How has technology changed your ability to travel, particularly to travel with less? 
It has given me quicker access to information which in turn has allowed me to learn a little about, and then make the decision to travel to, many more places than before, when technology didn’t play such a big role in my travels/life. As for traveling with less, in terms of possessions, I no longer needed guidebooks and in terms of money, I could now take advantage of websites such as Couchsurfing or contact bloggers to get some recommendations on ways to save money in a particular destination or meet up with locals through various websites, allowing me to enjoy unique experiences with actual people instead of spending tons of money on just visiting the “sights”.
As a follow-up, how has technology changed your interactions with and expectations of the people you meet, both locals and fellow travelers?  I’m particularly interested to hear your thoughts about the digital nomads who have followed in your footsteps.
I don’t think it has really changed my interactions much at all. At the end of the day, it certainly allows me to meet more people but when it comes time to interact, we sit down and learn about each other just as we would have done before technology. Sure, some people might read as much as possible about a destination and its people before they travel there and as a result, go in with certain expectations but I actually don’t do much preparation at all when visiting a new place. I prefer to just show up and see how it goes for the most part. With meeting other travelers/digital nomads, technology has given many of us a common ground that in a way creates an automatic bond before we even meet each other. And these days it is quite possible to have “close” friends that you interact with online but whom you’ve never even met. As for other digital nomads, with my own goals and work I need to do, I actually don’t spend too much time interacting with them. It’s nothing against anyone, I just prefer to do my own thing.
How did you come to meditation and what is your daily mindfulness practice like?
After I graduated from university back in 1999, I had a conversation with a cousin of mine who lives north of San Francisco and he recommended that I try a Vipassana meditation retreat at some point. And so I did, and it had a major, and extremely positive, impact on my life. Since that time, I’ve been to another 10-day retreat and I practice meditation as often as I can, something that I believe has really allowed me to be infinitely more present during my travel experiences and as a result, to notice, appreciate and learn from every little detail of the places I visit and the people I meet along the way.
You’ve written that a ten day vipassana retreat gave you what you call “an unexpected lesson” in not being judgmental.  Frankly, I think you’re being modest since your travel philosophy  embraces reducing misunderstandings.  Could you say a little bit about the connections you see between what you’ve learned from travel and meditation.  As a long-term traveler, what particular benefits do you see in doing a longer meditation retreat?
First, that initial meditation retreat I participated in was before I started traveling and so, at that time, I hadn’t quite developed my travel philosophy. But in the end, it didn’t take long to realize that nothing is ever as it seems and that we must absolutely experience the world for ourselves in order to learn what life is like in other parts. Even then, there is no way I would claim to be an expert on any destination or about any people or any situation in the world. I had my experience, I processed that experience and I reached my own conclusions. But there are hundreds of different ways to experience the same place and as a result, hundreds of different conclusions to be reached. So in the end, being judgmental or even thinking that we know the truth about something that we really know very little about, is quite a dangerous activity since there really is no possible way for us to be certain about anything. In terms of the benefits of a long-term meditation retreat, to be honest, I just want to do that for the personal challenge because even with such a retreat there is no way for me to know the benefits until I do it and going in with expectations would be against the idea of Vipassana anyway!
Great point!  Finally, your Wandering Earl Tours seem to have taken off nicely.  In addition to recently visiting Yemen, I notice you’re planning a Wandering Earl Tour to Iraqi Kurdistan.  Could you tell our readers a bit about how you’ve found travel to these places that typically are seen as dangerous has helped deepen understanding. 
This is not an easy question to answer because one’s experiences depend on so many factors. For example, if you don’t have much travel experience, I wouldn’t recommend going to Yemen or Iraqi Kurdistan on your own. But if you have some travel experience and are used to being in a destination where little English is spoken, where there is almost no tourism infrastructure or information, where things don’t work exactly as you hope, where the atmosphere might be a little more conservative than you’re used to, etc., then such destinations might be for you. I personally found Iraqi Kurdistan to be a very welcoming, safe destination, with a long list of interesting locations to visit. It was quite easy for me to travel around and I found it to be very relaxed and friendly everywhere I went. And I know many other travelers who have now gone and had very similar experiences. As for it being dangerous, it’s all about information. If anyone took the time to learn that Iraqi Kurdistan is a semi-autonomous region of Iraq, complete with it’s own border, and that there have been very few incidents of violence in this region since the war in Iraq began, they would probably have a different view. Instead, most people look at a map, see that Iraqi Kurdistan is in Iraq and immediately believe that it must be extremely dangerous as a result.
Shave in India


Leave a Comment
  1. Erin Elizabeth / Jul 17 2013 1:48 pm

    Just wanted to share my hilarious blog with a fellow traveler. Hope you enjoy it as much as I have enjoyed yours.

  2. Kristin Addis / Jul 22 2013 9:03 am

    I didn’t know he had done a ten-day retreat as well. Earl is definitely my chief travel guru. Great interview!

  3. A Mindful Traveler / Jul 22 2013 1:39 pm

    Thank you so much for your kind words Kristin!

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