Morfternight #70: Have you met Philomena Cunk?

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👋 ¡Hola! Greetings from Barcelona

On my way back from a meetup in San Diego, CA, I am making a quick stop in Barcelona, where I can meet three of my teams in just 48 hours.

I would have done that at any moment. Still, it seems even more critical now that I am headed toward a three-month sabbatical leave starting on Wednesday.

Meetups and sabbatical leaves are two things we do at Automattic that differ from many other companies.


Meetups are one of the critical components of a successful distributed company. Notice how I write “distributed” and not “remote.” The difference is that to be “remote,” there has to be a central location from which part of the company can be remote.

At Automattic, there’s no such thing.

Therefore, we are distributed across over 100 countries, and no one is remote. We work from our homes, co-working spaces, cafés, restaurants, gyms, libraries, or any location with a good connection.

In this context, meetups are a critical part of the fabric of our company. Spending a few days or weeks together every year creates bonds that help build and maintain trust and amplify our communication’s bandwidth.

The size and frequency vary. On average, we consider that traveling three or fours weeks per year is the standard (or at least it was pre-pandemic since we resumed traveling in 2022, we have kept it optional), but people in leadership positions often travel more to maximize the opportunities to meet everyone and create alignment.

Fun stat: in 12 years since I joined Automattic, I visited 144 different cities. Exactly one per month on average.


Automatticians have a three-month sabbatical leave every five years.

On Wednesday, I will start my second one. I am late on the schedule of one every five years because I decided to delay it a bit each time.

Sabbatical leaves are powerful tools; I can’t imagine why they are not more popular across modern companies.

They primarily serve three purposes:

  • Rest, fully and completely. Although we take vacations and have a very flexible policy in that regard, completely disconnecting from work takes a lot of time. Not only that, but even if a long vacation allows us to disconnect, then it’s over, and work resumes by the time that happens.

    Not with a sabbatical leave. 

    I still remember how energized I felt after my first sabbatical, and I look forward to that again.
  • Appreciate our work. Despite all the change and evolution one sees over five years, it’s perfectly normal to start thinking that it must be more fun elsewhere. After all, the grass is always greener on the other side of the fence.

    A sabbatical allows you to reset.

    Going away for three months is enough to remember everything we like about our current team, miss the people, and return recharged.
  • Test our processes and workflows. Of course, no one should be irreplaceable, and everything should be clearly documented. Still, it’s impossible to know if that’s true unless we regularly test the system.

    Each sabbatical is a small stress test.

    With a person away for three months, waiting for them to return for anything is not an option, so we test our ability to move forward without them.

🗺️ Three places to visit today

  1. They say evaluating a manager’s performance is easy by just looking at their team’s performance. If circular references are not your thing, here’s a decent article on the matter: Evaluating Managers: 5 heuristics to measure managerial impact.
  2. The Smithsonian is making a vast library of images, movies, and 3D models accessible for free and with a CC0 license, meaning you can use them in your creations and share those as you wish.
  3. If you are using GPT3 only through ChatGPT to ask questions, congratulations, you are keeping up with trends. If you want to experiment with the fun stuff, you need to step up your game.

🤣 Philomena Cunk

If you haven’t watched Philomena Cunk history lessons and interviews, you have been missing big time.

Once you get back from that rabbit hole and miss her, you can check Afterlife by Ricky Gervais on Netflix, where Diane Morgan has a great supporting role.

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