Why Barbados? The Importance of Remote Worker Meetups

One of the defining things about working at Automattic for a lot of people is the meetups. We fairly regularly meet up in different parts of the world to get to know colleagues, work on projects, etc. The location can be anywhere from Cardiff to Hawaii, and one of the latest trips I went on saw us travel to Barbados. This naturally has led to a whole host of questions, not least the staff of the hotel who bemusedly asked: “you came to work on the BEACH?”

Below I respond to the usual queries that people have, which will hopefully mean they make a bit more sense.


Why do you need to meet up anyway? I thought you’re meant to work on the Internet

Working at ‘home’ (or on a train, at your friend’s house, a coffee shop, the pub, in a hotel, on a boat…), and the flexibility that it brings is amazing. The autonomy that we have allowing us to  work our own hours, wherever we want, means that we can set up your schedule to fit your life, rather than the other way around. I personally work better in a number of shorter periods of time spread out across the whole day, so that’s usually what I do.

Communicating online, and working remotely is something that a lot of us have gotten used to from a young age. For me, it was spending time on IRC and forums when I should have been out drinking in the park, or whatever else Glaswegian teenagers are meant to be up to. As a result, it feels natural to develop friendships online. However, even for hardcore Internet geeks, meeting in person is important. Some of my oldest friends are those that I originally met online. The key distinction between them and others who I eventually lost contact with is that we ended up hanging out in real life too. Digital bonds can be strong and effective, but to really understand someone you need to spend some time together in person.

No matter how adept you are at online communication, the quirks of text-based speak (as opposed to voice, rather than mobile shorthand) mean that you can often be at risk of taking certain things that are said the wrong way, or not quite getting the intended meaning. I think sometimes people who are so used to communicating via digital mediums end up forgetting to inject their words with semantic meaning, so it can wind up even more difficult to read into.

The bottom line is: it’s important to meet people in person, especially if you are working with them daily. You get to know individual traits and idiosyncrasies, so that you understand how they come across online better. It means you have a better connection for when they next need to ping you to ask for help with something on Skype, and it’s not just an avatar staring back at you. This gives a whole different, and positive frame of reference, which makes working together a whole lot better (and more productive). The coolest thing for me is that moment when I can hear a person’s voice in my head whilst reading what they’ve typed out – that’s when you know it’s working.

You’re just away on a jolly!

On meetups, we always have defined projects that we will spend time on – ones that are easier to co-ordinate in person. That said, the point is not just about completing tasks. Infact, arguably the most important thing is getting to spend time with colleagues that you never usually get the chance to see, as I’ve explained above. It’s the longer term benefits from this that have the bigger impact than the short term gains from project work. If it was at anywhere else, it would probably fall under the aims of the dreaded, mandatory ‘company retreat’, with words like ‘team building’ and ‘co-worker bonding’ getting banded about. That’s pretty much exactly what the point is, except this time it’s done right. We actually want to spend time together, because we never get the chance to.

On top of that, I always used to wonder why businesses would spend so much money flying their sales people out to places like Australia and Chicago, to require them to return after just a day or two. To me, surely it made more sense to make the most of the expenditure on those flights in terms of personal development. If people are exposed to the cultures and places they visit, and able to enjoy them more, then they arguably become more happy in their jobs, and their knowledge about how to work with them grows. To me, it makes perfect sense to spend time in different places – your workforce becomes smarter, and more culturally aware – something which is an invaluable asset when working with customers from all over the globe.

So why don’t you work together all the time then?

Firstly, working together all of the time simply isn’t possible for a distributed company like Automattic. Employees live all over the world, where they choose, and so to bring everybody to one (or even multiple) places in a permanent fashion doesn’t make practical or financial sense. This isn’t even to mention the fact that doing so would go firmly against the independent culture that is so deeply ingrained in everything that we do.

Secondly, whilst seeing each other is awesome at meetups, it’s a fallacy to assume that it would be better to do that all the time. I love meeting up with other people, but I work far better when I’m in my wee cupboard office at home (or in bed, to be fair). At the end of a meetup I’m usually knackered, as it’s a pretty intense period of time to spend being social constantly when you’re not necessarily a naturally extroverted person.

Working remotely and meeting up every so often gives the best of both worlds: the independence and freedom to work where, when, and how works best for you, but also at the same time getting the chance to develop deeper bonds with people. Spending short bursts in person actually helps groups become closer, rather than elongated periods where they have to be.

Why do you need to go to Barbados though?! Can’t you go somewhere less exotic?

This is probably the one that most perplexes people. The fact that we met up in Barbados might seem ridiculous on the face of it, because of the distance from where I am, the weather, rum cocktails… everything. However, it makes more sense than might appear on the surface, for some of the following reasons:

1. Distance. Anywhere we pick will be far away from somebody. On our Barbados meetup, the majority of people were from North and South America, which meant that Barbados was actually one of the most central locations we could have found. Ironically, I had less flight connections going here than I would have flying to many cities in the USA, and the travel time was about the same as that to Chicago. I know where I’d rather be going, given the option.

2. Red tape. Bringing together a bunch of people from different countries means you need to think about visas, and border clearance. Whilst I’ve had a hard time at the American border a couple of times, that’s nothing compared to the hassle that some of our crew would have had to endure. (ever seen a Sri Lankan passport?) Barbados meant that all of our passports were accepted without a visa being required, and getting through customs was a breeze.

3. Language and Currency. In Barbados, everybody speaks English, and the currency is legally tied to the US Dollar at a ratio of 2:1. That means that people could use their own currency or credit cards, and there was no hassles when we were trying to organise things with the hotels or restaurants (not due to a language barrier anyway). Whilst you might want to avoid precisely those things when going on holiday yourself, they make life a whole lot easier for a week long meetup.

4. Cost. The price for the hotel, food, and everything else can wind up being a whole lot cheaper than you’ll find in either the US or the UK. The only thing to contend with then is travel costs, but these actually worked out comparable as well, given the location of Barbados, and the frequency of the flights.

The question really is – why on earth not go to Barbados? The food is good, the weather is great, the people are friendly, the beach is right next to the hotel…

Unless, of course, you have to have a terrible time for it to be considered work.