One Year at Automattic

Today marks one year on since I officially started working at Automattic, and it’s something of a tradition for Automatticians (or a12s as we affectionately refer to each other) to write up an anniversary post. I say ‘officially’, as technically it’s been well over a year. Each employee goes through a trial period as a contractor first, which was then extended further in my case by the relatively long notice period required in the UK. For the purposes of this commemorative post though, we’ll just go with it being a year.

Initially I wasn’t sure I would write anything at all. Why should anybody else care about my work anniversary? The more I thought about it though, the more I realised just how much had changed in the past 12 months, and how crazy it was that I even got the job in the first place. As more than one wise colleague told me back when I was hired: the first 6 months are a bit like ‘walking on air’, and it isn’t till you’ve been around for a bit longer that you settle into things properly. It makes sense to pause and take stock, rather than continue to let things hurtle by.

A lot has happened in the past year.

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The most visible thing (and annoying to everybody else who knows me probably) has been the amount of travel that I’ve been able to do. This is partly for work, and partly because of work; a result of the flexible schedules that we are incredibly lucky to enjoy.


I’ve been to San Francisco: the spiritual home for a lot of the online platforms we use today. The trip was both to meet colleagues, and also to check out the unbelievably cool HQ in person. I hadn’t seen my fiancee Grace in over a year, and Ingrid suggested I fly via Denver so we could be reunited for a week or so beforehand. Where else would do something like that?



I’ve also spent time in Hawaii with the forums squad…

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Drank rum and swam with turtles in Barbados




Explored temples and had rooftop BBQs in Mexico

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Met up with friends in LA, drank whisky and headed to the beach during a 9 hour layover

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Was reunited with the city of Chicago for a tech conference


Got the chance to live in Greece for a bit



and visit my family in Amsterdam


As well as that, I got to spend time showing Grace Scotland. This included discovering parts that even I hadn’t been to before… like Islay, the home of whisky.

Lagavulin - Islay


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Oban, Iona, and Staffa

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And we spent a lot of time south of the border in England as well… going away with friends to cottages in the Lake District to eat cheese and drink wine.

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or to take last minute trips to Liverpool to sort out the whole fankle that is the UK immigration process.

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I even had the chance to play host in my home city of Glasgow, combining work with pleasure (though the two seem hard to distinguish nowadays).

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Whilst the travel itself is amazing (and trust me, I know how lucky I am), it’s really the freedom that makes it possible in the first place that’s the most liberating part.

Without having to worry about budgeting my annual leave throughout the year, I can take time to go and visit friends or family – no matter where they are in the world. I can visit places that I would never have wanted to sacrifice my time off for before, because now I can always chuck my laptop in my bag and find a pub with WiFi to work from. This is especially true when it comes to discovering and re-discovering parts of my own country.

Then there’s personal life. I got engaged to a beautiful American girl almost two years ago, and it’s been a long and difficult process to finally get to be together. As you might imagine, moving away from her homeland to a strange place was difficult enough, but it would have been 100 times worse if we weren’t able to spend the amount of time together that we have, thanks to working remotely. We’ve been in the best possible position that we could have hoped for, thanks to getting a job with Automattic.

It’s not just the ‘where’ though, but the when as well.

Rather than meet the challenge of a small company spread out across the globe with more tightly controlled appointments, the opposite is true. There are no restrictions on the times I work at all, with the exception of a weekly team chat for an hour at a time… and even that’s up for negotiation.

My own schedule is… almost non-existent. Rather than squashing my time into a set frame five days a week, I spread out my hours and adapt to what feels right. Instead of forcing myself to sleep at 4am and having to get up three hours later to get ready to catch a bus, I wake when it feels natural. The removal of the pressure to be somewhere at a certain time (not to mention being presentable) has meant that for the first time in my life I actually sleep about 8 hours a night, rather than the 4 I always used to.

One of the consequences is that weekends are becoming less defined as time goes on. It’s common to not just forget what day it is, but also to lose connection with the feeling that that day should have. There’s no downer on a Monday, or excitement on a Friday, for example. Going back to work isn’t a chore, and Monday isn’t even really the start of a week any longer. Working when you are most productive means you might work 13 hours on a Thursday, 4 on a Friday, 5 on a Saturday, and 7 on a Sunday, so the whole structure of life begins to lose the meaning that it was previously infused with.

This doesn’t work for everybody, but it does for me.

For the past year, it’s felt like I’ve really lived, rather than just living to work.

Then there’s the actual work itself.


Every day I work with software that both myself and a large chunk of the web rely on for our websites. My team in particular fight to defend freedom of speech; protecting our users from censorship, and highlighting when companies try and abuse their position on the web. It’s something I’m very proud to be a part of.

To top it all off, I can count some incredibly smart and hard-working people both as co-workers and friends.


Something that has really hit home over the past year is that if you want to achieve something, you’re the one who has to make it happen. More than a platitude: you can’t sit around and expect things to drop into your lap, or put decisions off until you are 100% ready; you have to just go for it.

Here’s to many more years. If you’re like minded, there’s all sorts of cool open positions with Automattic here.

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.

Thoughts on (Flexible) Working From Home

It’s been a few weeks since I started working from home for Automattic, engineering happiness for users of

Having moved from an (almost) standard 8.30-5pm, office-based working day, the switch has proven to be an interesting experience.

Even with my youth squandered in online tech communities that operate in very similar ways to Automattic, it’s definitely a mindset shift to go from that sort of world being just something that you do, to something that actually pays the bills. Work is meant to force you into set patterns begrudgingly… right? I didn’t expect there to be too much of an overhaul, but a job with complete flexibility has definitely brought with it some interesting quirks.

happy monday - working from home

Here are some of my observations:

You don’t get distracted

One of the usual reasons that people give for ‘not being able’ to work from home is that they get distracted and can’t concentrate on what they’re meant to be doing. As far as I’m concerned, that’s nonsense. Sure, it may well depend on the person, but if you are independent and self-motivated, you shouldn’t find it a problem to set out an area and dedicate the time you need. If a Gen Y-er can do it – with our alleged ridiculously short attention spans – then so can you.

Going to the bank isn’t the headache it used to be

Ahh… the dreaded trip to the bank/post office/travel agent/loanshark. It was always such a torture to have to undertake any sort of task that fell during the working day. This equally applies to the receiving of parcels. Sure, you can get small things delivered to work, but what happens when you order something big? Carting it back from the office is never a fun task… even if you are lucky enough to have access to a car. Working from home sweeps all of these troubles away in one fell swoop.

Your Neighbours Will Love You!

If you play your cards right, that is. So long as they’ve met you (and you’ve not been weird about it), you can easily become a local everyday hero. Just make it clear that you’re usually around during the day if they have parcels getting delivered, or need an eye kept out for something. Even if they never actually ask you to do anything, you’ve won major brownie points – especially handy when you throw that 7am-finish party with all of your dubious mates.


Lunch is better

The first week I worked from home, I ate nothing but bacon sandwiches – purely because I can. That can’t continue for long though, or I’ll balloon to some ridiculous size. In general though, it means you have access to your own kitchen, rather than an awful, over-priced canteen (or a microwave, if you’re lucky). I was never any good at avoiding squashing my sandwiches anyway, so this is a winner. The only real dilemma is… what to have? So much choice!

You get to mock those who have to commute

I’ve luckily managed to avoid travelling every day during the onset of the Scottish winter this year, which is undoubtedly one of the greatest perks about being based from wherever you choose.

It’s pretty soul-destroying to wake up early, in the dark, to make your way into work, only to return home at night, in the dark. What has never made any sense to me though, is the preposterous notion that people should fight their way for hours through gridlocked motorways in the rain, sleet, and snow, to get to an office to do a job that they could arguably do just as well from home. I’d even go so far as to argue that it’s negligent for employers to expect people to physically come in to work on days where the police are ‘advising motorists not to travel’.

That said, I think there are those who genuinely love this sort of daily battle, as if there is some sort of valour to be had in succeeding in such a pointless trip. Those, my friends, are those whom we should mock relentlessly.

Electricity bills

Uhhhm, Leave this one with me.

You can go hours without saying a single word to anybody

Insert your own joke about how it’s better if I keep my mouth shut here. There’s a lot of commentary about how it can be unproductive to be constantly interrupted in an open plan type office, and it’s definitely true. The flip-side is the total opposite though. Unless you live with other people, you can go entire days without uttering a single word. I’m not entirely sure whether it’s a completely zen-like experience just yet.

Watch this space.

The banter

This is related to the above. Sure, there are a lot of downsides about working in close proximity with over folk – like having people hang over your shoulder, or force you to look at links on the Daily Mail website (shudders – Linda, you know who you are!), but you can’t really beat the days in work when you’re surrounded by people who are working on the same thing, having a laugh together.

You need to make more of an effort to stay in the loop

This could well be partly because I am refusing to pay for a TV licence, and so am missing out on the news at night, (disclaimer: I don’t own a TV, or watch it as it’s broadcast online) but more often than we think (yes, even in the age of so-called ‘new media’), news is spread by word of mouth, through the people we come in contact with every day.

If your community is online rather than round about you, very quickly you might find that you aren’t as up to speed on local happenings as you might have been previously. It takes a real effort to keep up to date; a battle that I am currently losing, it has to be said.

You can find your natural schedule

I’ve never been a fan of mornings. Not that I don’t like the crisp, fresh air; the tweeting of the birds; and all that. I simply don’t function well at that time.

Part of the problem is that due to whatever screwy Circadian rhythm I have, I don’t naturally get tired until around 2-3am. Irrespective of how early I was up at in the morning, the time I went to bed remained the same. Working from home, I’ve shifted to a 10am-6pm day (roughly), which already means if I go to sleep at 3, I’m getting 7 hours sleep, compared to 4. That’s almost double the amount, and has meant I feel 100% better during the day, with no irresistible urge to disco-nap early evening.

Working from bed is the best thing ever

…for a few hours anyway.

Days seem shorter

Even though I am working the same number of hours, and finishing up the same time I would be getting in from work if I was commuting, the days still seem to fly by. Those extra 3 hours spent getting up, getting ready, and travelling to work in the morning have been converted into sleeping hours, which is probably what they should always have been in the first place.

life work balance

Concepts of time become more fluid

Weekend? What’s that? With total flexibility, there comes a blurring of the lines between the ‘working week’. When you are able to choose a schedule that fits around your life, that may not be in traditional daily blocks. Many people will shudder at the thought of the lines between work and personal life ‘blurring’, but that isn’t really what’s happening. Just because work becomes spread more diffusely, doesn’t mean that it takes over; it just allows you to integrate it more closely to what fits best for you. Working two hours in the evening or at the weekend instead of on a Monday morning doesn’t mean you are a slave to the job, it means that you are more in control of how and when you choose to give it your full attention.

When you spend all of your time in the one place, with work spread out more than beforehand, It does mean that weekends never feel quite like they used to.

I don’t actually think that that’s a bad thing, for what it’s worth.

People don’t get it

‘But… How do they know you’re actually working?!’

Engineering Happiness for

happiness engineer
My interpretation of a happiness engineer turned out a bit horror film-esque.

I am more than excited to say that I’ve accepted an offer from Matt Mullenweg – founder of WordPress – to join Automattic as a full time Happiness Engineer, beginning at the end of November.

With just a shade over 200 employees, Automattic’s network gets more monthly unique visitors than,, and It’s not too far behind Facebook either… They support some of the biggest names on the web, like CNN, TechCrunch, and TED, and get about 19% of the world’s web traffic.

‘Based’ in San Francisco, almost everybody works remotely – from locations around the world. I’m the only employee north of Manchester, which is pretty awesome in of itself. From what I’ve seen, they have an amazing culture with some incredibly smart, and talented people. I’m pretty blown away at the chance to be part of it all.

All that said, it’s been great working with Amor Group, – where I started out 9 years ago as a fresh-faced, terrified schoolie. They’ve been good to me over the years, and I’m particularly proud of what we’ve managed to achieve with their digital communications. I wish them all the best as they go forward as part of Lockheed Martin, but it’s time for me to bow out.

I’ll leave you with this, the Automattic creed:

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.