Living the Dream – Work Anywhere in the World

December 12, 2016
Peta working remotely

My career goal in the past 3 years has been to have a fulfilling career that will enable me to work anywhere.

I had an operations position in a small startup. As with most startups, this meant I did a little of everything – marketing, HR, financials, logistics, admin.

I had spent a few weeks here and there proving that working from a remote location was possible – there had been a few weeks on Vancouver Island on the West Coast of Canada and a few weeks in the UK where everything had gone very smoothly, bar the occasional phone call where it had been a little challenging to find a quiet corner amongst 10 of my closest family members!

Work Anywhere - Victoria, BC

Last year I really got a chance to put it to the test with a 7-week sailing trip to the Caribbean. I maxed out my vacation time and spread that vacation time evenly over the 7 weeks, which took the pressure off needing to be available at a specific time. Going into it I really wasn’t sure what the wifi (or even the power) situation would be like. We were generally planning to be anchored rather than docked which would make it unlikely that we would ever have wifi while onboard.

Work Anywhere - Beach Bar

My favourite beach bar – unfortunately there was only one power outlet nowhere near a table which resulted in an operations manager, an author, a graphic designer and an artist all crouching over one very overloaded multi-adapter!

I’m Canadian and had a US roam-like-home plan meaning that I should have been able to use my data when we were near enough to US islands. Unfortunately, that was only going to be for a week or so on this trip. I had mixed results for the rest of the trip. There was only one location where we managed to anchor close enough to an island to get wifi on the boat (Saba – the small one off Virgin Gorda, not the more-challenging Saba Island where the only anchorage is next to towering cliffs with no hope of wifi!)

Unfortunately, the wifi and power might not be at the beach bar on your favourite beach. They may be in the hottest, humid Laundromat.

Work anywhere - laundromat

That was an unpleasant 6 hours

Although I definitely did some research before leaving on my sailing adventures there were certainly some things I hadn’t thought about such as how important a good quality dry bag is if you’re going to be schlepping your laptop to and from shore in a small dingy!

Here are my top 7 things you should consider before you decide to work anywhere (be it on the road or on the ocean):

Invest in a laptop

…with an excellent battery if you’re going to be traveling anywhere that power might be a concern. I had a newish MacBook that served me very well, but I was on the boat with Dani, a graphic designer, and Nikki, an author, who both had a number of power issues throughout the trip. Bear in mind that even though you may be traveling to locations with power, prolonged power outages can be extremely common depending on the country or region you are visiting.


…as much as possible before you go. Even if you want to wing-it as much as possible, take a look at places you THINK you might go. Looking at expat websites, blogs from students abroad or sites such as Nomad List can be extremely helpful when trying to find good wifi locations to hang out and work. When my business partner, Sue, worked in Costa Rica at the beginning of this year, although her research showed that she would have wifi in almost all the areas she planned to visit, she discovered that often wasn’t the case, or that the internet was extremely unreliable. She ended up with a $400 cellphone bill to cover the data she needed to use while she was there.

Consider culture

Don’t assume all coffee shops will be happy to let you hang out with a coffee and work indefinitely. In the Caribbean I encountered places that wouldn’t give out their wifi password until you had ordered food and others that clearly didn’t want people on laptops.

Check access to your platforms

For example, Google doesn’t currently work in China so if you’re planning a trip, don’t transition all of your files and emails over to Google a couple of month before leaving like my friend, Barry did recently (He proceeded to spend a very long month with his only access to email being via his assistant reading them and then sending him a synopsis via WhatsApp. He would then send a voice note for his assistant to transcribe and send via his email – it was doable but certainly not ideal!)

Be Realistic

Before you commit to certain number of hours and particular hours you will be online, think carefully about what is realistic for the place you are going and the goals you have for while you are there.  Aim to under-promise and over-deliver.

Don’t leave yourself stranded

Before you leave, compile a list of work to be done and documents that you can work on when wifi is not available. This can be challenging depending on your job, but there are usually some things you can still do offline. A backup of ye-olde-printed-documents can be useful if being without wifi AND power is a possibility for some of your trip.

Be patient

When traveling, wifi can be very slow. In the Caribbean, this was not so much of a problem for me, but for Dani, this meant sending design files back and forth to clients was a challenge. On one particular occasion she had to sit on the steps of a bar almost all night long!

Work-Vacation Balance

Before you go, think about your goals, think about what you want to see and consider your personality.  Do you need some time away from everything? If so, make sure you carve out some of your time away as a proper vacation without feeling compelled to do some work each day. If you just want a change of scene you can spread your work more evenly.  While Sue was in Costa Rica she found that alternating a day of adventure with a day of work meant she was a lot more able to stay focused on her working days. While I was sailing I planned to be in locations likely to have the most reliable wifi on a Monday. I would work for as long as possible on those Mondays and then spread the rest of my work across the workweek leaving my weekends work-free.

Don’t come back from your “work anywhere” trip and realize that all you really know about a place was learnt in a handful of places that had great wifi. Wherever you go and whatever your goals, don’t forget to enjoy where you are and relish in the freedom you’ve managed to achieve!

Written by Peta Williams in an Ikea restaurant overlooking the beautiful North Shore mountains in Vancouver BC whilst eating a 99c breakfast.

Work Anywhere - Ikea Richmond

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