The Secret of Travelling Trinis … 10 jobs to enable your travel dreams

It’s Tuesday and you’re bored at home or you’re fed up with traffic on the highway  or you’re just thinking about changing scenes because you’re tired of the same liming spots with the same conversations. What better way to shake things up, than by changing everything and just leaving Trinidad for some adventures across the globe – to be that Travelling Trini. Regardless of what happened, you’ve realized that you want to travel,  you don’t have a million dollars (USD, not TTD … since TTD ent really worth two shits!) and you have to earn money while you do it. But Rishi, I don’t have money or a sugar daddy to pay for everything for me, so “How ah going to just leave Trinidad jus’ so?” … well intrepid readers, here is something that you might not have thought about – you could just work on the road!

In spite of the recession and all this economic doom and gloom, there are a ton of jobs you could be doing and getting your travel on. You don’t even need to have superstar qualifications, MENSA like IQ or a 44DD chest size – although having the latter does help with finding a “dotish” sugar daddy who will pay your way (nothing like working on your back … the hours are short, the labour is little and there are health benefits). In fact, there are many of these jobs that do require extensive travel or even relocation overseas – and what’s better than someone paying for all your expenses to move abroad and have new adventures?

Now before you start packing your bags, do realize that some travel jobs pay better than others … for instance, being an international spy like James Bond pays very well, but you need to also be James Bond … last time I checked, he was also not a real person, and chances are that, if you looked like Daniel Craig, well you would have some nice sugar momma paying your bills. So in that vein, I’m going to outline a couple jobs that only require someone who can speak English and put on socks and shoes – showering is optional, but it does help.

  1. English Teacher:
    Nothing says unqualified, searching wanderer like English Teacher. Nothing also says confused waste of space who graduated with an Arts degree like English Teacher but that is a completely different article. I’ve never taught English before … although I’ve been told that the Trini accent is a sexy accent, which should help things on the social side, but pity the poor Koreans/Japanese that you’re going to be teaching. English teaching jobs are easy to find in many parts of the world and all that’s required is a random university degree and/or ESL certification. The Japan Exchange and Teaching (JET) Program is one of the best English teaching gigs, but there are countless other opportunities in every corner of the world.
    You will have to put some research into lifestyle and cost of living in the country, you’re going to be teaching in. Japan and Korea pay well, but it’s also expensive to live there, Thailand and Vietnam are also popular options, since there is a better lifestyle and lower cost of living. Latin America is always great, but you’ll need Spanish a lot more over there. If you’re looking for information, then check out Dave’s ESL Cafe.
  2. Join the Army … yes Trinidad has an army!
    Even the TT regiment has specialized positions that require training and course that require travel. If you’re lucky to hold a green card, then you can join the US Army – they have a lot more travel opportunities, and I’m not including Afghanistan on that list.
  3. DiplomatYou can join the TT Foreign Service. Speaking some foreign languages will definitely help, but pretty much if you can surf the Internet, hold good conversation and push tons of paper, then you my friend are a highly qualified candidate. There are some downsides likes being all along and not being able to find doubles and saheenas on demand, you might even have physical danger … did you see Argo? Moving around every couple years might also not be the best thing for your relationships (but think about how much “Outside man/woman” you could have!). This being said, on the bright side, you’re going to be living in a style and comfort that you would have not gotten, if you were an English teacher. Here are a couple links to life as a diplomat … Diplomat/Foreign Service Officer/Specialist, Being a DiplomatLife of a Diplomat
  4. Tour guide
    This is an obvious one – but it would have required you to have left the comfort of Port of Spain and already be living that country, which is not really the situation you’re in, if you’re reading this article. Right? One option for wannabe tour guides is to seek out a tour company in the area and apply for work. While in many cases it may be necessary that you’re fluent in the local language, speaking English can definitely be an advantage, as many of your clients will likely speak it as well. Another option is to work as a freelance guide, particularly if you have a niche or specialty area, such as local cuisine or outdoor activities.
  5. Work for the United Nations
    My dad worked for the UN. He went all over the world to such far flung places like Serbia and Kosovo. It’s hard work and you’re going to be in some rough places, but think about all the awesome adventures you’re going to have. You might even get to ride in a tank and hold weapons – it’s one of my Dad’s favorite stories. Now you’re going to ask, “How did he get the job?” … well he went through an agency. One agency like that in Trinidad is Eve Anderson and Associates … here’s the link – I’ll take the commission in Angostura 1919 please.
  6. Cruise Ships
    You don’t have to be a sailor to work on a cruise ship. The only qualification for some of the jobs is that you just have to “Not get seasick” … yep that’s it! Cruise ships offer tons of on-the-water travel job options – the more qualified you are, the better job you’re going to get, but I met many Trinis who were working on the cruise ships. Your sexy accent will help get better tips and swag with the men/ladies. If you’re a dancer and can “bruk out” … even better. Seriously!
  7. Au pair
    An au pair is essentially a nanny or babysitter that may also do light housework.

    • The positives: families that can afford this are typically wealthy, meaning you may experience gourmet meals, private chauffeurs, and free vacations to resorts.
    • The negatives: You will have to work with babies who crap a lot, you might even have to work with adults who crap a lot.
  8. Travel Writer
    Being a travel writer is super easy … it’s like getting an Arts degree. Being a good one and making a living out, is a completely different story – but if you will be sent to review and write about places and hotels. However, if you can write fairly well and are web-savvy, it’s possible to sustain your travels on writing income alone – there are many of travel bloggers, who travel tons and get paid to write about it – but they’re not getting rich doing it.
  9. Work on a yacht.
    How about working on a luxurious yacht? super fancy, rich people need crews to help them get around, and qualified sailors with good people skills can travel the world in style by hanging out in fancy ports and making connections with the global elite. Check out Bowen Marine and hang out at the T&T Yacht club.
  10. Online Poker Player
    You need ZERO business skills or academic qualifications … like none! You don’t even need people skills … in fact, this is a job where people skills are actually a bad thing. Now before you quit your day job, you should read many a forum … like this one. I can personally speak to this one … I actually considered this a couple years ago, while stuck in a casino in Niagara Falls … I then realized that I wasn’t that good – and I still made money, but the lifestyle is actually super stressful and super lonely.
    Online poker is a lot of fun as a hobby, but playing for a living is quite different and is a decision that should be carefully thought out before quitting your day job. There are some great benefits to playing online poker for a living:

    1. You can work your own hours.
    2. You are your own boss.
    3. You can take as much vacation as you like.
    4. You can work wherever you want in the world.
    5. You can work in your underwear 😀
      Obviously, poker has some inherent risks that are part of the job. You will have an unstable income each month with the risk of actually losing money during a month. Even experts can play hundreds of hours and still lose money. To play professionally, you need to be the type of person that can handle these fluctuations. Although they shouldn’t happen too frequently, they will occur, and believe me they are not much fun.

There you have it … a couple suggestion on to become a travelling Trini.

About Rishiray

Rishi Sankar is a Cloud HRMS Project Manager/ Solution Architect. Over the past 15+ years, he has managed to combine his overwhelming wanderlust with a desire to stay employed, resulting in continuing stints with 3 major consulting firms (IBM, Deloitte, Accenture). He documents his adventures around the world on "Ah Trini Travelogue" with pictures and stories from the road/tuk-tuk/camel/rickshaw. You can follow him on Twitter at @rishiray and on Facebook at "Ah Trini Travelogue . He doesn't like Chicken Curry but loves Curry Chicken and is always trying to find the perfect Trinidadian roti on the road. He also doesn't like cheese and kittens ... and definitely not together. E-mail from his blog is appreciated like a 35 yr old Balvenie at

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