Every five years, Automattic encourages its employees to take a three month, paid sabbatical. Different people make use of this in different ways. Some undertake once-in-a-lifetime journeys; others indulge in the realisation of passion projects; while others still ‘just’ relax and unwind. The breadth and diversity of these choices reflect the attributes of the folks themselves, and it’s always really fascinating to hear their stories and experiences when they return. Irrespective of any individual preferences, there’s no doubt that the sabbatical provides an incredible opportunity to pause, reflect, and ultimately explore the value and meaning of a precious commodity: time.
Prior to heading off in 2019 for my first sabbatical, I wrote a post on this very blog, talking about what I hoped to do, or ‘achieve’ (if that is the right word) over that period. As I’ve now been part of the company for over a decade (gasp), I am therefore eligible for my second – and will be taking it later this year.
As I started to think about what I wanted to do this time around, it struck me just how similar the goals and desires I came up with were to those that I had back in 2019. In fact, pretty much every single one of the 10 things that I laid out in my prior list could easily equally apply again now – and probably will actually – to a greater or lesser extent. Some people might find that boring, or even concerning. After all, why on earth would you choose to do or focus on the same things, rather than try something entirely new?
I do understand that inclination – and want to ensure that I allow space to experience and explore novel situations. However, I also want to really deliberately make time for those parts of my life that either bring me comfort, or which I am passionate about. The types of thing which I love doing, but rarely get the chance to sink into in the manner which I would like.
In some ways I think about this like deciding on a restaurant to eat at. Going to a new place can be rewarding, but also potentially disappointing – and sometimes you just want to go to your favourites. The tried-and-tested. The familiar and dependable. Often, you might realise that you haven’t even been there for months anyway. I’m aiming for some balance, with that in mind.
While the sabbatical is still a few months away, I wanted to outline in advance some of the goals, aims, and expectations I have, as they will help shape and guide the decisions and plans that I make. So, here they are:
- Go places. Getting away from Glasgow to explore and experience different parts of the world might be a predictable entry, but one that is also really important. In practice this will mean returning to places I have been before and enjoy – such as spending a few weeks in Tokyo and Seoul – but also discovering others for the first time (such as Prague). I am hopeful that other opportunities will also present themselves along the way, and I’ll be in a position to grab them.
- Enjoy Scotland. Somewhat in contrast to the above, I would like to savour the place that I live. Scotland can be an incredible place in the summer, and I haven’t really been around to make the most of it in years gone by. I’d like to enjoy that – whether it’s taking the dog to the beach, sitting in the park with a book, or taking a trip up North to areas that I’ve never been before.
- See Friends. Rather than sit in the house staring at my laptop, I want to get out and spend time with people – particularly those that I may not have seen for some time, or who live far away. I would rather this be in more interesting or creative ways than just ‘getting drinks’.
- Create. This is an important one. I want to dedicate time, energy, and space to making things – primarily music. Hopefully, this will lead to something I can actually share, such as an album.
- Perform. This is related to the above, but I’ve deliberately split them out, as they are distinct. It’s been a wee while since I last performed live, and I’d like to do that again. However, it has to be the right opportunity. There’s no point in just doing it for the sake of it. Hopefully the universe will present some interesting possibilities.
- Say Yes. One of the memories that sticks out from my last sabbatical was a friend dropping me a message to ask if I’d like to go up in a tiny private plane that he was transporting across the country early the next day. The realisation that there was nothing preventing me from just saying yes!! was incredibly liberating, and it was an amazing experience, that I wouldn’t have had otherwise. In a similar vein, I want to create the space for the serendipitous to happen, and jump on the chances when they come along.
- Tend to the Garden. I am taking some artistic license here, because I don’t mean literally gardening. Instead, I mean reflecting, re-organising, and bringing more of a purpose to parts of my life that have perhaps been neglected. That might mean something like tidying out a cupboard that I’ve been putting off, but could also be more meta-physical.
- Do Something Totally New. This is probably self explanatory, but I’d like to break out of my comfort zone. In some ways it’s linked to ‘say yes’. However, this is more a deliberate reminder to seek out and commit to trying something completely novel. One thing I’ve been considering for a while is training to be a Legal Observer for protests and demonstrations. Perhaps now is the time to do that. Maybe I’ll take an improv class. Who knows.
Most of all, I just want to embrace the freedom of not being bound to a particular schedule, or structure. One of the biggest frustrations I have had over the past couple of years has been the feeling that it is all too easy to get stuck in routine, and I want to make sure that I resist that where possible over these months. That will of course be easier said than done, especially given that my wife will still be working, and I can’t just up and abandon her or the dog – but it is a principle that I am going to strive for.
A concept that I’ve been thinking about a fair bit recently is the idea of being intentional. Approaching situations deliberately, and not just letting them slip by without consideration. Questioning what you want from an interaction or day, and then acting with that in mind. Squeezing the lemon. Whatever I end up doing, I hope I’ll bring that mindset.
I’ll report back afterwards.


























