Globetrotting Entrepreneur Glen Wakeman: What It Really Takes to Work Abroad


The often-romanticized life of the long-term traveler is something we’ve all dreamed about while sitting in the confines of a monotonous day job. Perhaps your social media feed is populating with friends’ photos from exotic locales, or it could be that a recent vacation left you wanting more. Or maybe you’re just tired of your immediate surroundings. Whatever your desire may be, the allure of traveling the world while still being able to support oneself can seem like the holy grail of a lifestyle. Though this idea may seem far-fetched at first glance, it’s actually quite achievable. Read on for a comprehensive guide to traveling and working abroad, with insights from an expert on the topic, Glen Wakeman.


Who Is Glen Wakeman


Glen is an established globe-trotter who has perfected the art of melding travel and work through, among other things, a twenty-year career at his old job. If you’re looking for insights into how to thrive in your career while seeing the many sights the world has to offer, Glen Wakeman can serve as a valuable resource.


The Benefits of Travel


Before we can dive into the best ways to travel and work abroad, it’s helpful to look at some of the many benefits that travel can offer. Here is Glen on the subject:


“I’ve learned through my travels in Europe, and Asia, and Latin America that there are a lot of different ways to approach things. A lot of different ways to find joy and success in life. And, also, different value systems. All of that translates into a far more complex, rich, and enjoyable perspective on choice and how one leads a company.”


The type of perspective increase that he’s talking about here is a commonly-cited benefit of travel. It goes without saying that the world is a large and diverse place with a myriad of different cultures who approach situations in different ways. The exposure to such a variety of problem-solving methodologies is not only interesting in its own right, it’s something that can help you when you are faced with challenges of your own.


Here are five other ways travel can help improve your life:


  • Relieves stress
    • Studies have shown that the stress-relieving effects of even a short vacation can linger for weeks after a trip.
  • Enhances creativity
    • Creativity can often be stifled by monotony. By breaking out of your daily routine, you may help your brain make creative connections it otherwise would have missed.
  • Improves social skills
    • Being away from your usual group of friends and acquaintances forces you to meet new people. Connecting with strangers exercises your ability to interact socially.
  • Aids language learning
    • There’s no more effective way to learn a language than through immersion. A trip to a country that speaks another language can save you countless hours of study at home.
  • Strengthens tolerance for uncertainty
    • While traveling, you’ll inevitably find yourself in situations that don’t go as planned. By working your way through these types of experiences, you improve your ability to do so again in the future.


Working While Traveling


For many people, living abroad for a long stretch of time means they need to figure out how to make money while they travel. Of course, working internationally helps support one’s travel aspirations, but many find that there are other tangible benefits to working abroad that compare favorably to working in one’s country of residence.


One major benefit of this pursuit is the ability to learn of a country’s culture through the way in which it conducts business. While many travelers only ever see a country through the lens of a tourist, those who work in the country gain an extra perspective on life in the workplace. Once again, Glen Wakeman has insights to provide in this area.


At a certain point in his career, Glen Wakeman found himself working in Brazil. During that time, he noticed that his management style was not as effective as he’d come to expect from past work experiences. Suspecting that the situation may have been a result of cultural differences, Glen sought advice from someone he trusted.


“I understood that things weren’t working well, I was self-aware. So, I did, I think, the wise thing by seeking advice from someone that could bridge the cultures for me. They explained to me, when you come into the office say hello to everybody. Don’t just immediately dig into the numbers, which would be more of a US-style of doing business. Instead, actually engage with the people as people. Understand them and their lives. Then from there, go and conduct business. That was a really powerful learning circumstance for me.”


By experiencing this aspect of Brazilian culture firsthand, Glen was exposed to something that many other travelers to the country are not. While it is certainly not necessary to work in a country to appreciate its charms, many find that the unique perspective of the workplace provides an opportunity to glimpse a part of society that remains veiled to many travelers.


Jobs You Can Find Abroad


Okay, so you’d like to work abroad, either for some extra traveling funds, increased perspective on a country’s culture, or some combination of these and other reasons. But the question remains, how do you find work in other countries?


Admittedly, it can be more difficult to find work in other countries than domestically. Although, it is getting easier by the day as the world becomes increasingly interconnected. As Glen says:


“The wonderful thing about technology is you’re liberated. You have freedom of geography. Every place in the world can offer you Wi-Fi. So, you can bring your work with you, be it on a laptop, or tablet, or whatever.”


The types of jobs Glen is referring to here are often called remote positions. The sky is the limit on the kinds of work you can find on the internet, but we’ve compiled a few of the more popular positions that will allow you to work from any location, be it a beach in Tahiti or a mountain in Nepal.


  • Virtual Assistant
  • Transcriber
    • Watch videos and transcribe the audio into written text.
  • Writer
    • Create blog posts, articles, website copy, and other written pieces for people and companies looking for content.
  • Language Tutor
    • Connect with language learners online to help them practice speaking your native language.
  • Graphic Designer
    • Create graphical content to be used by real-world or web-based organizations.
  • Social Media Manager
    • Run the social media accounts of influencers and/or companies as you help them build their brand and grow their following.


Along with the above remote-style jobs, the enterprising traveler can find a number of positions based in the country in which they are traveling to. While these positions are certainly more beneficial in obtaining the aforementioned cultural perspective, they also may require more work in terms of obtaining permission to work in the form of special visas or other allowances. Here are a few job options that can serve as a jumping-off point for those looking to work abroad.


  • Bartender/Server
    • Not only is food service a career with opportunities across the globe, it also has the potential to be lucrative depending on the tips you can earn.
  • Au Pair
    • Another term for a live-in nanny. If you’re good with kids, these jobs can be well paying and usually come with room and board included.
  • Tour Guide
    • As a traveler, you have a unique perspective on what may be of interest to those visiting from your home country. By working with a local tour company, you can use that perspective to entertain and inform tourists who are looking to take in the sights.
  • Translator
    • If you’re bilingual, this can be a very lucrative trade. You can work in live translation or translating written text. Either way, it can be a great side job to earn extra cash.
  • Hostel Staffer
    • Many hostels will allow travelers to stay for free in exchange for services such as working reception, cleaning, or acting as a point of contact. Free housing goes a long way towards supporting a growing travel habit.
  • Seasonal Jobs
    • Many international destinations thrive on seasonal tourism that temporarily causes a surge in workforce demand. By arriving in-country before the high tourism season begins, you may be able to find a job tied to that country’s specific needs.


Logistical Considerations


Some people who embark on extended travel for the first time find that they encounter difficulties for which they are unprepared. While unforeseen circumstances are certainly part of the charm of seeing the world, it’s always best to get ahead of planning logistics so that you’re ready for a variety of eventualities. In this section, we’ll discuss some tips and trick for what to consider in advance of any large trip.


One of the big things that comes to mind when preparing to travel is what to pack. Though this can be highly dependent on the location to which you are traveling, below you’ll find some things to keep in mind when deciding what to bring. If you come across any areas you are unsure of, make sure to research them before you leave for your trip.


  • Weather
    • This may seem like an obvious one, but it can actually be tricky. Parts of the world that may be known for specific weather conditions can actually have a significant amount of variation over the course of the year. Check seasonal weather patterns and forecasts for an idea of the weather at the time of your trip.
  • Infrastructure
    • Some parts of the world lack infrastructure that you may take for granted in your home country. For instance, a lack of clean drinking water may lead you to bring a water filter. Lack of reliable electricity might necessitate a solar charger. Make sure you’re well aware of the infrastructure at your destination before you travel.
  • Transportation
    • Will you be walking a lot, or will you be taking taxis everywhere? Do you need a map (be it physical or on your phone)? Do you get motion sickness on long bus or boat rides? The answers to these types of questions might change the things you choose to pack. Know in advance how you’ll be getting around.
  • Currency
    • ATMs may be uncommon in the country to which you’re traveling. The same goes for credit cards. Many locations may require that you bring cash as a form of payment. Being able to pay for goods and services is an important part of getting around.
  • Health
    • Do you need travelers insurance? Are you able to purchase needed medication in-country, or do you need to bring it? Are there any additional health items you may need during your travels? Health concerns while traveling can range from inconvenient to downright disastrous. Make sure you’re prepared.




One area that you might also be concerned about is learning the language of your destination country. It’s certainly useful to learn key phrases, and most people will appreciate any effort you make toward communicating in their language. You may also be surprised at how much you can communicate even if you don’t know the language of the place you’re in. Glen has this to say on the subject:


“I found that, in my travels, people are incredibly forgiving and tolerant if you’re polite. You don’t need to master languages or understand nuance and culture if your basic approach to the society is to just try and be polite. Golden rule type of stuff. You’ll find that societies, in general, are really welcoming.”


Where to Travel


The question of where to travel is primarily one of personal preference. You probably already have areas of the world you’ve always wanted to explore. To that we say, go for it! All travel experiences are, however, not created equal when it comes to ease of getting around and general exploration. Those who are new to traveling may prefer areas that are more accustomed to tourism, and therefore have more resources available to the neophyte explorer. When planning a trip, the internet is a great resource for determining how popular a particular location is. Glen’s recommendation here is to start with what you know.


“If I had never traveled I’d probably start with places that seemed familiar to me. I would always read about the places so I knew what to expect. Then I would go explore. But I think the ability to use technology as a tool to liberate oneself, makes it very feasible in the 21st century.”


If you’re a US traveler looking for specific recommendations, you may find starting off with a trip to Canada or Mexico is a great way to get started. Many Americans find European countries to be easier to travel to as well, since they’re used to accommodating travelers from all over the world. Parts of Southeast Asia are also known for their friendliness to tourists. In fact, Glen’s favorite country to visit is in that region of the world.


“My favorite place to travel was Thailand, precisely because it was so different from where I grew up. I’m from a little manufacturing town in Connecticut. I found Thailand to be exotic. Thailand means land of smiles. They’re some of the kindest and most diplomatic people on the planet. It’s very diverse. It’s geographically beautiful. It has its challenges, but I really enjoyed my time there because I saw it as not just exotic but as wonderful.”


Just Do It


When considering an extended trip abroad, it’s easy to think of reasons to opt out. Many people feel their responsibilities at home preclude them from being able to travel. Others worry it may be too expensive. Still, others may have some fear of venturing into the unknown. If you find yourself hesitating to commit to a travel plan, our advice is to reexamine the benefits of travel and think of all the good a trip can do you. Here are some parting words from Glen Wakeman to further extrapolate on how travel can help improve your life.


“I think that the fact that I’ve had to explore, live, and succeed in different societies created an ability for me to have more nuanced understandings of things. Definitely more patience. And, therefore, helped make me a better executive, employee, and person.”


Remember Glen’s words the next time you find yourself longing to take off and explore the world. The benefits are immense, and the obstacles can be overcome through planning and persistence. Refer back to this article if you need a refresher on the reasons to get going and the ways you can do it. After all, if our lives are a collection of experiences, then we’d do well to make sure our experiences are worth collecting.

More about travel genius Glen Wakeman at


  1. It is for sure that traveling the world brings new experiences and joy. I really admire the way he chooses to live and work. Being able to learn new cultures, new languages, new people and see the world from different perspectives makes you value more what you have, and change something on better.  The world is offering many possibilities to us, we just need to grab the right one. 


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