Meetup Magic

I’ve spent the last week¹ in Tulum, on Mexico’s beautiful Yucatan Peninsula, for an Automattic meetup. And as usual for these kinds of work gatherings, it was magical (and, after many recent departures, a welcome opportunity to feel a closer connection to those of us that remain).

Dan and four other men stand around a firepit, in front of a tropical beach and a twilight sky. — Obviously, meeting in-person with my immediate team² was a specific goal for the event.

Only after deciding the title of this blog post did I spot my own accidental wordplay. I mean that it was metaphorically magical, of course, but there also happened to be more than a little magic performed there too, thanks to yours truly.

Dan standing on stage in front of a seated audience; a screen behind him shows a close-up of his hands holding several playing cards. — I made magic a theme of a “flash talk”. After that ~350 people was a suboptimal audience size for close-up magic and offering to later replicate the trick I was describing in-person to anybody in the room… I ended up performing it many, many more times.

No, I mean that the whole thing felt magical. Like, I’ve discovered, every Automattic meetup I’ve been to has been. But this is perhaps especially true of the larger ones like Vienna last year (where my “flash talk” topic was Finger for WordPress; turns out I love the excuse to listen to other people’s nerdity and fly my own nerd flag a little).

Beautiful sunrise, with reds, oranges, yellows and pinks dappling across the clouds, seen from a Caribbean beach. — There’s plenty of reasons it was a magical trip, as I’ll explain. But after arriving late and exhausted, this view from the doorstep of my bedroom the following morning was a great start. I made a habit of a pre-breakfast swim each morning in the warm Caribbean waters.

Our events team, who are already some of the most thoughtful and considerate planners you might ever meet, had gone above and beyond in their choice of location. The all-inclusive resort they’d booked out for pretty-much our exclusive use was a little isolated and not the kind of place I’d have chosen for a personal holiday. But it provided all of the facilities my team, sibling teams, and division could desire for work, rest and play.

One day, I returned to my room and discovered that in the course of their tidying, the hotel’s housekeeping team had been asked to tidy up any stray charging cables using reusable Automattic-branded cable ties. These are the kinds of nice touches that show how hard our events coordinators think about their work³!

As usual, an Automattic meetup proved to be a series of long but energising days comprising a mixture of directly work-related events, social team-building and networking opportunities, chances for personal growth and to learn or practice skills, and a sweet sprinkling of fun and memorable activities.

Stalactite-strewn cave deeply filled with clear blue water. — A particular treat as a trip to swim through a *cenote* – caverns formed by sinkhole erosion of the limestone sediment by rainwater, often considered sacred to the Maya – complete with fish, bats, and the ugliest spiders you’ll ever see.⁴

Harvey Mackay said⁵ that if you choose a job you love, you’ll never work a day in your life. That might not ring true for me every day of my working life, but it certainly feels significant when I’m at Automattic meetups.

Two men and two women sit around a sticker-covered Macbook laptop, collectively looking at its screen. — Work that feels like fun, and fun that contributes to work? Is that the secret sauce? My colleague Boro and I certainly tried to bring that energy to our workshop on the philosophy of code reviews, pictured.

Our meetups might not feel like “work” (even when they clearly are!), but rather like… I don’t know… a holiday with 400 of the coolest, friendliest, most-interesting people you could ever meet⁶… which just happens to have an overarching theme of something that you love.

Even the appearance of Hurricane Milton, which briefly threatened chaos to the peninsula before it was determined that its path was definitely dominated by a Florida-ward direction, couldn’t dampen our spirits but did bring us some of the most spectacular fireworks nature has to offer.

Recently-developed changes to strategic priorities, and the departure of a few of our colleagues during the recent aforementioned “realignment”, meant that my “superteam” – my team and its siblings – had a lot to talk about. How can we work better together? How can we best meet the needs of the company while also remaining true to its open-source ideology? What will our relationships with one another and with other parts of the organisation look like in the year to come?

Dan sits with seven other men in an ourdoor bar area, with water trickling down an ornamental wall behind them. — All the best meetings take place in bars, right?

Every morning for a week I’d wake early and walk the soft warm sands and swim in the sea, before meeting with colleagues for breakfast. Then a day of networking and workshops, team-time activities, meetings, and personal development, which gave way to evenings with so much on offer that FOMO was inevitable⁷.

A group of people lie or sit cross-legged on towels in front of a collection of musical instruments. — I continue to appreciate the ways that Automattic provides the time and space for me to expand my horizons. Whether that’s at one end of a spectrum learning a new technical skill. or at the other sitting-in on a “sound bath”⁸.

Automattic remains… automaggical to me. As I rapidly approach five years since I started here (more on that later, I promise, because, well: five years is a pretty special anniversary at Automattic…), it’s still the case that routinely I get to learn new things and expand myself while contributing to important and influential pieces of open source software.

Our meetups are merely an intense distillation of what makes Automattic magical on a day-to-day basis.

Dan lies in a hammock under a warm sun, smiling. — At home, I usually start my day with a skim of my RSS reader from bed. But with the sea calling to me, first, each morning of the Tulum meetup, I instead had to suffice with reading my feeds from the nearest available hammock to the beach on my doorstep.

Did I mention that we’re recruiting?

¹ Travelling light, as has become my normal.

² Excluding the two who couldn’t make it in person and the one who’s on parental leave.

³ Another example might be the pronoun pin badges that they made available in various locations, which I’ve written about already.

⁴ The spiders, which weave long thin strand webs that hang like tinsel from the cave roof, catch and eat mosquitoes, which I’m definitely in favour of.

⁵ Okay, fine: Harvey Mackey isn’t the original source, and it’s not clear who was.

⁶ Also, partially-tame trash pandas, which joined iguanas, agouti, sand pipers, and other wildlife around (and sometimes in) our accommodation.

⁷ I slightly feel like I missed-out by skipping the board gaming, and it sounds like the movie party and the karaoke events were a blast too, but I stand by my choices to drink and dance and perform magic and chat about technology and open source and Star Wars and blogging and music and travel and everything else that I found even the slightest opportunity to connect on with any of the amazing diverse and smart folks with whom I’m fortunate enough to work.

⁸ While I completely reject the magical thinking espoused by our “sound bath” facilitator, it was still a surprisingly relaxing and meditative experience. It was also a nice chill-out before going off to the higher-energy environment that came next at the poolside bar: drinking cocktails and dancing to the bangin’ tunes being played by our DJ, my colleague Rua.