Working Overseas | Interview with Wandering Earl

Wandering Earl (AKA Derek ‘Earl’ Baron) was one of the first travel blogs I discovered when I was researching creating my own site. I almost instantly became hooked by his writing style that combines an uncanny storytelling ability , humour and travel savvy that might be lacking from somebody with less than 12 years worth of experience overseas. I’m thrilled that he’s taken time out of his busy schedule to engage in a topic based interview discussing his experiences overseas, and more specifically, the almost seamless transitions he’s made from one career to another. It would be impossible to cover everything he’s done since December 25, 1999, but the following paragraph from his ‘about’ section on his blog offers a bit of a glimpse:

The adventure has involved over 70+ countries (view the list here) on 6 continents, work as a Tour Manager on board cruise ships, two years in India, experiments with meditation, muse-creation, mountain-climbing and movie acting, volunteer work, an inappropriate amount of time on tropical islands and eating inappropriate amounts of street food, a two-day kidnapping, being placed on the US ‘terror watch list’, teaching English in Asia and a fruitless search for a pair of sandals with sufficient arch-support for my flat feet, among others.”


1) When you first took the plunge and journeyed abroad on December 25, 1999 how long did you originally expect to be gone for?

My plan was to backpack around Southeast Asia for 3 months and then return home to find a job to settle into. It never occurred to me at the time that I would be away for any longer than that period of time which is why I bought a round-trip flight ticket from the US to Bangkok and back.


2) You’ve been travelling/working/living abroad in some capacity for 12 consecutive years! What keeps you motivated to continue on with this sort of lifestyle?

It’s the education. I really don’t care much for major tourist sites or popular destinations as my travel addiction is fuelled by the everyday interactions that I have with people that I would never have come into contact with had I not decided to travel. And it is these interactions that provide me with a first-hand education about this world that I simply cannot receive through any other method. So as long as there are more countries and more cultures for me to discover and learn from, the motivation to continue travelling will remain as strong as ever.


3) You certainly have a fascinating resume – one that covers a lot of diverse jobs and working conditions overseas. In hindsight, what is one job that you’ve done that you’d least likely want to ever do again?

There is not a single job I’ve done that I wouldn’t do again. Each of the positions I’ve held, whether it be teaching English, working on board cruise ships or earning money online, have all played an important role in my life. I enjoyed each of these jobs at the time I held them and if I had to, I would go back to any of them without hesitation. The way I look at it is that if I can find and obtain employment in a position that helps me to achieve my travel goals, then I have no right to complain at all!


4) Is there any advice you could give for somebody who is currently sitting on the fence unable to decide whether they can take the risk of leaving home to explore the world by travelling or working overseas.

Don’t delay. Stay focused and find a way to make your travel dreams a reality. Follow travel bloggers, email them, ask them questions, learn from the experiences of others and you’ll discover endless ideas that will help you get started. And all you need is enough confidence in yourself to take that first step, because once you do start traveling, an entire world of incredible opportunities will appear before you, most of which you never even knew existed. There is no way of knowing where you’re life will end up once you begin your adventure, but you need to take that first step to find out!

Also, don’t let finances affect your decision too much. While you will need a little money to get started, I think many people are quite surprised to discover that traveling doesn’t have to be expensive at all. There are so many regions of the world where $500 is more than enough money for one incredible month of travel! For example, places such as India, Southeast Asia and Central America are all destinations where even the most budget-conscious of travelers can travel in comfort.

And the one thing I always remind people who are trying to decide whether or not to travel is that you will almost never meet anyone who regrets having made the decision to get out there and explore the world. It may be challenging and daunting to get started but the rewards of travel are so unfathomably great that it’s almost a guarantee that your experiences will have an incredibly positive effect on your life.

5) You have extensive experience working overseas as an English teacher and on board a cruise ship. If you had to compare each job versus one another what are a few pros and cons of each?

When it comes to teaching English, the pros include being able to actually live overseas and immerse yourself in a new culture as well as there being opportunities for foreigners to teach English in dozens of countries around the world. On the other hand, the cons are that you are generally required to sign up for a one-year contract and apart from vacation time, you won’t be doing much traveling outside of the town or city where you live/teach.

With cruise ship employment, the pros are that you are able to earn and save a great deal of money in a short period of time while traveling around the world and meeting and connecting with people from dozens of different countries. However, the travel aspect really only involves having a few hours of free time while the ship is in port, so it is more of a taste of travel. Also, working on ships requires you to work a 4-6 month contract and for many positions, you have to share a cabin with someone else.

With all of that said, I have still yet to find any other form of employment that offers the same earning, networking, socializing and work experience potential that cruise ship positions offer. It is by far the best method I know of to help aspiring travelers start saving money while traveling at the same time and as a result, gain the freedom needed to chase after one’s goals in life.


6) You’ve written a popular ebook entitled: How to Get a Job on a Cruise Ship. What are a few areas you specifically cover in the book that makes it such a valuable resource for those seeking employment in this area for the first time?

The idea of this eBook was to instantly eliminate the need to embark on a frustrating search for information on how to apply to cruise lines. It is extremely difficult to find such information online and so, using my own personal experience and industry contacts, I’ve created a resource that instantly provides every piece of information one needs to apply and get hired.

The material covers which cruise lines are best to work for, how to properly format a resume and cover letter specifically for the cruise industry, interview questions and tips, detailed advice to guide you through the entire application process, job descriptions for dozens of positions along with approximate salaries and the specific contact details for every department of 18 major cruise lines and over 25 concessionaire companies. In addition, every order comes with unlimited email assistance which means that I will personally, and thoroughly, answer any questions regarding the application process. This gives customers a direct link to someone who knows exactly what the cruise lines are looking for in potential crew members.

7) In recent years you’ve transitioned from various kinds of employment to having your own online business. What motivated you to make this shift and what have been some of the benefits of being self-employed while living a location independent lifestyle?

There just came a time when I realized that I needed to have a little more freedom in my life in order to pursue and achieve some of my other life goals. And so I began to do a little research about alternative methods of earning income. When I discovered that people were starting to earn money through a variety of online endeavours, I decided to give it a try myself and I spent a full year on my laptop trying to get started. That was three years ago and I’ve been working online ever since.

The benefits of such work are endless as I can now work from anywhere in the world as long as I can find an internet connection. Also, I obviously have no boss to report to and my income is generally related to the amount of work I choose to do. So in the end, I’m in complete control of where I live, where I travel, how much I work and ultimately, how much I earn. And for someone who is addicted to world travel, this is as perfect a setup as I could imagine!


8 ) In the past you’ve alternated between working and travelling abroad with distinct shifts from one to the other. What is it like now where you are working and travelling at the same time? Do you find yourself having to make compromises at times with regards to what you can/can’t do in order to fulfil necessary duties to maintain your online income?

Actually, at this stage, I still try to separate my work and travel as much as possible. I’ve been able to create a system that allows me to spend 2-3 months living in one place (my most recent location was Mexico) where I spend my time fully dedicated to working on my online projects. Then, after a few months, once I’ve caught up with work, I’m able to take off and travel somewhere new for 2-3 months without having to spend much time on my laptop.

It was about a year ago when I realized the need for such a change as prior to this, I often found myself frustrated at having to spend hours and hours on my laptop when all I wanted to do was get outside and explore the destination I was visiting. I quickly realized that working online and traveling at the same time really is an impossible task if you’re constantly moving around.

In the end, my theory was that instead of having to make compromises, I would rather split my time so that I can be fully dedicated to either travel or to my work without having to mix the two too much. So far it’s working well!


9) You’ve travelled to over 70 countries. I hate to put you on the spot but if you had to choose the one country that’s left the biggest impression upon you, which one would it be?

India. This one country has made such an impression on me that I’ve now visited 8 times and spent over 2 years in total traveling, living and volunteering throughout that land. I simply have yet to find another country that offers such an intense and life-changing education. Barely a minute passes without seeing, hearing, tasting or smelling something that you have never before experienced and the result is a constant need to re-evaluate everything you’ve learned about life up until that point. And because I travel to learn, India has proven to be my ultimate classroom.

10) What’s the biggest shift or change in the way you travel over the past 12 years from when you first began up until now?

When I first began traveling, I found myself more interested in checking countries off of a list and filling up my passport with stamps than I was in seeking out the most rewarding experiences possible. And so I would bounce around from town to town and city to city, rarely ever staying more than two or three days in one location. My goal was not necessarily to gain as extensive an education as possible at the time but instead, to just travel for the sake of travel.

Then, as the years passed, I slowly began to realize that my travels were not as valuable if I didn’t travel with a specific goal in mind. So with each new adventure, I began traveling more slowly and with more of a purpose. Sometimes I would visit a country to learn the language or to meditate or to live comfortably while catching up on work or to learn how to surf or to celebrate a specific festival. And the result was an increased satisfaction, not only with each of my specific adventures, but with my overall decision to live a life that involves such constant travel.

These days, I travel very slowly, almost always spending at least a week in every town, city or village I visit. It’s actually not uncommon for me to spend a month in one place, not only to immerse myself as much as possible in the local culture, but also to ensure that I spend time trying to achieve the goals that I have set for myself for that particular trip.

Basically, I no longer care about the number of stamps in my passport as I now care much more about the handshakes and conversations and smiles that I exchange with new people every single day that I’m on the road.


I encourage you strongly to follow Earl’s journeys on his travel blog, Wandering Earl and connect with him on facebook and twitter. For more information about his book, ‘How To Get A Job On A Cruise Ship’ click on the banner below.

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  1. says: Mike

    I absolutely love interviews like this and thank you for sharing Derek’s story with us, Samuel! I was most interested in the cruise ship work as that is something I’ve considered after retirement. Not too keen on bunking with another though – just a me thing. I would so enjoy the “off the record” stories about that job! I may look into the eBook too. Thank you for this post! 🙂

  2. Happy to have learned more about Earl. I can 100% agree India is the place to be! I haven’t left in 1.5 years and don’t plan on doing so anytime soon! I think I’m going to have to get knocked up or something so I can find a way to legally stay here forever haha

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  6. says: Arbind Ojha

    I agree with much of your talks and south east asia is having so much to see and lean from there. My great thanks to you for sharing your experience.

  7. says: Josh

    Thanks for posting this interview. I found it really interesting, especially his view on how travel has changed throughout the years. I am one that loves to get stamps on my passport so maybe I should consider better stories and less stamps as he recommended.

  8. says: Cornelius Aesop

    Thanks for this post, I’ve come across this ebook before but never bookmarked it. This time I was sure to do so and will hopefully put this to use, and likely purchase it after I’m finishing land roving around South America.

  9. Great interview with Earl! He’s taken the more unconventional approach to travel with his work on cruise ships. With all his travels, I think his stories from his times on a cruise ship have been the most eye-opening showing how hard the work can be. I enjoy Earl’s travels!

  10. Awesome interview, Samuel. You don’t always read travel interviews with such great questions specifically tailored to the interview subject. Earl makes a great point about how hard it is to write while always moving around. It’s easier to travel for a while, then slow down and write about everything you saw.

    1. Thanks Scott! I think constantly trying to combine both travel and work (full throttle) would burn just about anyone out. As you mentioned, slowing down gives you time to not only relax but to also reflect on everything that you’ve done up until that point.

  11. This was a really great interview – very useful and interesting!

    We actually work and travel at the same time. It is a little stressful, but as long as we travel slowly it mostly seems to work for us. We tend to stay in one place for a month at a time, then go out and explore the area about three days a week and work the other four days (with some flexibility, of course).

    1. Christy, that sounds like an ideal routine. I’m looking forward to hopefully being able to do this in the future myself. It sounds like the work hard / play hard split seems to be common amongst digital nomads and the most ideal way to strike a balance.

  12. says: Leif

    I totally agree with you about India, Earl. I have never found a place as far from western culture as India. My only beef with India is it’s sometimes very funky food and the subsequent squirts that ensue. I bet both you and Samuel can attest to that >< 🙂

    1. says: Earl

      Hey Leif – So far I’ve been lucky with the food in India and have only once been sick as a result. And since I love all types of Indian food, I can help eating everything I see while I’m over there! But you’re right, it is not enjoyable at all when stomach issues arise over there…

  13. says: Erin

    It’s always a pleasure hearing more from Earl – he has such great advice. Working on a cruise ship seems like a great option for someone who doesn’t have the money to travel right now. We have a similar system to Earl where we work on our online business in one place for a few months and then travel around for a few months – you do need that work time.

    1. Erin, the system that both you & Earl are using sounds ideal. I think if you were to constantly be online while traveling it would take its toll. The work hard and then play method sounds great. I’m hoping that within a year or two I can transition from teaching to being a full-time digital nomad. Hearing these kinds of stories gives me confidence even though I’m quite weak in terms of my knowledge/experience in this field.

  14. says: ciki

    Great interview Sam! And coincidentally, Earl is featured as blogger in the spotlight on my blog today as well! haha;)

    Yes I totally agree that in Southeast Asia 500 bucks can go a long way. That’s why it’s so easy to get around and have a comfortable life whilst traveling in our part of the world:) I did learn some new info on Earl, from this interview, and he does look dashing in uniform;) ahem!!

  15. Great interview. I have followed Earl for two years now on twitter, but I have not read much of his blog. This post will motivate me to read more. In fact, I think it is time I subscribe.

  16. says: Margo

    Great interview! Love learning more about my friend, Earl. Someday, after I pay for my daughters’ fancy educations I’m going to leave my perky suburb and surprise the heck out of him by going somewhere other than France or Italy 😉

  17. says: Earl

    I really appreciate you interviewing me Sam! I always enjoy answering such questions as it offers me a chance to not only reflect on my experiences but to ensure that I remain focused on my goals in the future. And this interview certainly helped me accomplish both 🙂

    1. Thanks Earl, you really answered the questions with a lot of detail and gave thoughtful answers. I think your philosophy on travel is something a lot of others could learn from and I can see why you continue to feel inspired to roam around the globe with this kind of attitude.