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Travelling the world for work, is it the dream?

September 19, 2020

The Great Working Dream: worker by day, traveller by night, flying around the world for meetings, meals with clients and the occasional full working day from the hotel. One week Dubai, the next Japan. Suited up from 9 to 5 and a bathing suit for after hours. Is this all we have made it up to be? Or are we intentionally turning a blind eye on the darkest bits of living half of your life on airplane food? 


I set out to Instagram to find out whether it was just me who has wondered for a lifetime if this really is the dream or if I’m being too naive imagining living life out of a suitcase. Aka, a magical Mary Poppins suitcase that fits my entire closet. Now that’s the dream…


The winning side was surprisingly powerful, on a poll made on my Instagram Stories, more than 80% of people agreed with me, and I will let you know that doesn’t happen often. At least 4 out of 5 people believe in dreams, soaring high above the sky and working remotely from a beach in Bali. So, I dug deeper. How blindsided are we by the magic of it all?


Dina Silva (@dinasilva.ig), former Regional Director of the Four Seasons Hotels & Resorts, for the past 2 years, agreed to speak with me, so that together we could rip apart this fantasy and understand what truly lies beneath the surface.


Dina is no stranger to travel, being Canadian-born with Portuguese parents, her working life started out in Toronto, but soon flew her to Lisbon, Portugal. Maputo, Mozambique was her home for three years but work later took her to the Middle East, where she has spent the past two years living in Dubai. Most of her life she has worked in finance, but like many of us she is multi passionate and embraces projects in areas as diverse as wellness, art and sustainability.


Here’s the deal, sit down for this, Dina’s job was to go from luxury hotel to luxury hotel around part of the globe, checking the hotel’s standards…


*Dramatic pause*


Technically, she was a regional director for Europe, Middle East and Africa. “The main part of my job was to travel to the various hotels we had in those regions, which was about 39. So, I had to travel, not to all 39 in one year, but we would do about 15 per year. My responsibility was to ensure the company’s operational and financial standards were effectively being [met] by the property. On average I was at each property from 5 to 8 working days”


See what I mean? How dreamy does this sound?


But my true question is, is it all a bed of roses, or can we get caught up in the thorns?

Four Seasons Bali | Picture Credit: @dinasilva.ig


“First and foremost it depends on you, and what sort of things do you value in terms of your lifestyle. For me, not having any family commitments, it was very easy to travel on a regular basis”, Dina explains. She recounts that in total she would spend about 10 staggered days a month at home in Dubai. “It became very difficult for me to be involved in any community work. I like to do a lot of volunteer work, I’ve always done that throughout the years and it just made it very difficult for me to create a settled routine in my home base. That for me was the biggest con.” One of her biggest issues was, as well, maintaining a healthy lifestyle in terms of sleeping and exercise, as there was barely any routine. “After the first 6 or 7 months of travelling like this, I quickly realised it was becoming difficult to maintain healthy habits.”


Another big issue was food. *loud cinematic horror scream*


“If you have a great gastronomic experience when you travel, then the trip was good, if you don’t, then the trip was ‘mehhhh’” - I will quote this for the rest of my life.


“In my case, I was staying at the hotel and my work day would begin early morning and end well into the late evening. You can’t say 9 to 5 anymore, it’s more like 9 to 9 or 9 to midnight. You ended up eating quite a bit, because you are automatically forced to have 3 three big meals. You would normally start off with a meeting in the morning with breakfast, later have lunch with your colleagues and inevitably, in the evening, they would organise some sort of business affair around dinner, which I felt obliged to attend. Because I am a foodie, my colleagues would take me for dinner outside the hotel so I could have a taste of local fare and some experiences were very surprising…like I will never forget eating fried bugs in Mexico City. So, there was a lot of eating, not necessarily good eating and that didn’t contribute to a very healthy lifestyle either.”


Sad disappointed face emoji…


However there are still pros, which are, as Dina suggests, very easy. “The cultural experience is hands down the best. I love to travel, I have no problem getting on a plane and dealing with airports. The whole administrative part of it wasn’t a problem. I didn’t really get jet lagged at all. Being able to experience and seeing a city, getting a taste for the local flare, the people, the art, the sights, that was all definitely very enriching.”

Moscow | Picture Credit: @dinasilva.ig


However, and I stress this as a big however, YOU HAVE TO PLAN IN ADVANCE. No free spirited travel here, plans, organisation and reservations will have to become your mantra. “The first couple of trips I did, I didn't actually build in time in my schedule to be able to go to certain places, so the trip just became all business, and I quickly realised my time wasn’t mine anymore. I got smarter by the third trip and I would plan to arrive earlier or I would plan to leave a bit later. Also, ahead of time I would research the city, figure out what I wanted to see or where I wanted to eat and I would try to slot those in, so that I could do the city my way. However, I was able to do this because I had the liberty to do my own schedule, but sometimes you may not have that, depending on what stage of your career you’re in.”


After reflecting on my life expectations, I asked Dina what did she miss the most about home.


“Probably my bed… *laughs*… I have a very comfortable bed, and although I was sleeping in very comfortable beds too, there’s nothing like your own sheets”.


On the flip side, when leaving, apart from the cultural experience, what she looked forward to the most was connecting with new people. “You do really have an extended network of people you connect with automatically, that you meet in all of these different cities, it’s wonderful to carry on these connections long after the job is finished.”


Nevertheless, this is an exhausting lifestyle that may not be easy to endure by everyone for a long period of time. “I think there’s a few factors that go into it. The type of lifestyle you want to have, whether you are or want to settle down and how much control you have over your schedule. For me, the lifestyle wasn’t so much the problem, settling down wasn’t an issue either, it was the schedule. I started to feel burnt out after about 13 months of non-stop travel, it just started to feel really taxing, because of the flying, meetings, reports, deadlines and then not being able to exercise regularly quickly turns into an unhealthy cycle. My take-away is that if you have the ability to freelance or control the pace at which you travel and work, then you could probably do it for longer, but my limit ended up being about two years.”

Istambul, Turkey | Picture Credit: @dinasilva.ig


After having been all over the globe, Dina says she would still like to live in Dubai a bit longer, as she was travelling all the time, there was hardly any time to take in the city and its surroundings properly.


Next on her bucket list, India is taking the crown, but it is soon followed by Japan and Greece.


Essentially, there are no right answers here. The dream is built by each one of us, being fed by dreamy instagram posts and tales of a perfect job no one dares to admit they don’t have. What matters for each one is what factors in The Great Working Dream. Whether we need to be close to our loved ones, whether flying is not our thing or even if having a healthy lifestyle is our main priority, THE dream may not be much more than that, a dream. Still, as a personal opinion I don’t see its viability in the long run, however I’m dying to try it for a while. See you soon, somewhere else.


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