Automattic Meetup – Denver, November 2022

I have now been working with Automattic – the company behind WordPress.com and Tumblr – for a grand total of nine years. In that time we’ve grown from a scrappy crew of less than 200 people to over 2,000 of us. According to the internal tracker, 94% of Automatticians started after me, which is hard to wrap my head around. Distributed across almost 100 countries, we work ‘remotely’, but get the chance to see each other in person at varying intervals.

Over the years I have been fortunate enough to meet some really fascinating and smart folks, and spend time with them in amazing places all over the globe, including Hawaii, Paris, Whistler, and Serbia…

I have always enjoyed going on these trips, and have many fond memories from them. There’s something pretty incredible about having a network of people around the world that you interact with on a daily basis over the Internet; then suddenly being together in person for a full week: eating; working; drinking; dancing; and sometimes staying up all night talking about the most personally involute of topics. The intensity of those kinds of experiences inevitably means that you can quickly form deep and long-lasting connections.

Despite all of the intrapersonal implications, I’ve never really been one to get particularly emotional about the time shared – at least not to the extent that this would manifest physically. God forbid the idea that I would be the kind of lachrymose individual prone to shed a tear when it comes time to say goodbye. While appreciating all of the innate complexities of these encounters, I am usually good and ready to head home by the end: weary, but satisfied. However, when 400+ of us gathered in Denver recently, that was notably not the case at all.

In many practical ways, this particular meetup was relatively unremarkable. Due to the number of attendees, we were based in a large hotel, with meals, various workshops, and meetings held in their amorphous halls. However, out of all of the trips I have been on as an Automattician, this more than any other stirred up the strongest emotional response. Even well before the final day came around, I could feel an impending sense of sorrow looming at the prospect of having to part ways with this group of erudite but authentically unassuming and fascinating people. When the goodbyes did inevitably come, they were accompanied by sore hearts, swallowed tears, warm words, and lingering, repeated hugs. The sense of sadness was profound and palpable; caught me completely off guard; and is something that I’ve ended up carrying with me all the way back to Glasgow.

Despite having a rather fantastic seat on the plane, I spent the entire homeward journey staring into the darkness; reflecting on why this particular meetup had triggered such an unexpected emotional reaction. Some of these are naturally too personal to share on a public blog, but the list of possibilities seemed endless. In plainly practical terms, perhaps it was the impact of COVID, which had meant many of us hadn’t been in the same room for many years. Maybe it was due to the relatively short duration of this trip (four full days rather than six or seven). The events at Twitter and elsewhere in the tech economy could always have played a part subconsciously… Despite intellectual rationalisations, I’m not convinced that any of these responsible. Perhaps the truth is a much more complicated farrago of circumstances, and it probably doesn’t even really matter if it can be nailed down or not.

Whatever the environmental factors may be, there were a number of occasions in particular that stood out as noteworthy, even at the time. On one of the nights, a group of us were sitting outside the hotel doors, huddled up around one of those permanently burning fire pits. It was freezing cold, and there wasn’t any necessarily any especially deep or interesting conversations going on, yet nobody seemed to want to leave; content, and with a perceptibly genuine desire to just be around each other, without any particular expectations or pressure. It is a moment that was almost poignant purely for how unremarkable it was. That kind of unspoken, shared natural comfort that develops in spaces without a defined ‘purpose’ or scheduled activity feels increasingly special, when really it shouldn’t be at all. There was something about that place, at that time, with those folks that felt particularly significant, for whatever reason.

As a male from the West Coast of Scotland, we have a tendency to do our best to avoid any kind of sentimentality, lest what we feel be trivialised, ridiculed, or outright rejected. We can be some of the warmest, most open hearted people you will ever meet, but also keep our personal thoughts and feelings closely guarded. This isn’t even necessarily out of a particular simplistic conception of what a ‘man’ should be, but rather from a belief that we won’t be understood, and that we should just get on with it and deal with difficulties ourselves. No matter what I might be struggling with in my personal life, the idea of sharing any details of that in work is simply unthinkable, and so any experiences like this which manage to puncture through somehow inevitably set off a string of existential questions.

Why did this experience mean so much to me? How can I maintain these bonds or connections with people while remote? What does this mean for my normal life? Are there things I need to re-examine or change? How do I take the positivity of these moments and apply them outside of these settings? Was it only me that felt this way? Have I given too much away by being vulnerable with my emotions? How do you make any changes without doing that? What if these moments can only ever be moments? Should they be? Am I just sleep deprived? Is this really something I should be writing about? What will people read into all of this? etc…

There aren’t really any good answers to any of these ruminations, and maybe there doesn’t need to be. Undue introspection is something I’ve long since battled with, but I am usually much better at suppressing it than this. Whatever the case may be, the time spent with these folks has been incredibly valuable, and I hope I get to see them again as soon as possible. Even if it has to happen remotely, I hope that we can find a way to nurture and deepen the connectedness that has sparked over the past week. I’m sure we can; it will probably just take a bit of concerted effort.