Don’t forget: you’re going to die – All the awkward shades of Automattic Grand Meetup

Why would anyone want to talk about death? It’s an immensely overwhelming topic, and almost everyone sensibly stays away from it. Unless you were personally affected by death in recent past, you won’t probably want to chat about it, and even then you’ll be extremely careful to do that. Death is an ultimate conversation killer, and bringing it up at a dinner party is sure to result in blank stares, awkward silence, and people keeping a safe distance from you, just in case.
If there’s one thing more awkward than talking about death at a dinner, it’s talking about it in a business setting. Business isn’t the right place to ponder about metaphysics, and considering your own mortality hardly ever contributes to company revenue. On the contrary, thinking about death you might suddenly discover that you’re wasting the best years of your life in a job you don’t actually love that much, quit, move to New Zealand, and buy a sheep farm.
Sounds kinda weird, doesn’t it?

But Automattic is no ordinary company

And so our annual Automattic Grand Meetup started with our CEO Matt Mullenweg talking about growth, pain, and death. He recommended an iOS app called WeCroak that sends friendly reminders several times a day saying: “Don’t forget: you’re going to die”, and a browser extension that displays an estimated number of days you have left in your life. He spoke about how thinking about death can help you stay grounded and focused on what’s most important.
Most people weren’t prepared for this, and neither was I. In result, we tried to conceal the awkwardness with jokes. One of our colleagues wrote a WordPress plugin called “Hello Death” that displayed similar deadly reminders in admin Dashboard. Another one sent the same messages as a newsletter subscription test. Throughout the rest of the meetup, we’d reply to all sorts of situations with “don’t worry, we’re going to die anyway” and in most cases it was met with giggles. But this was a weird, dark kind of humour, and few people seemed to actually enjoy it.

Thinking about death is always a step away from hopeless despair

Everyone knows it that, of course, we’re all going to die, but hardly anyone tries to fully acknowledge it. We repeat smart-sounding phrases about how “death is what gives life meaning”, or that “only if you conquer the fear of death you can truly live at last”, thinking that pretty much exhausts the topic. However, as long as you’re satisfied with repeating someone else’s words about something, you won’t actively try to discover the truth for yourself. Which is understandable – the process of discovery is usually terrible and heartbreaking, and few would sign up for it voluntarily.
At some point however, there comes a moment, usually brought about by loss and grief, when you can no longer hide from the raw awful truth. In a few years or a few dozen, you’ll be here no more. Everyone you ever loved will cease to exist. Everything you considered dear is going to fall apart. Everything you ever achieved is soon going to be forgotten.
In a few generations, no one will even know that you existed.
It’s quite depressing and unpleasant to ever think about this. Even if you believe in an afterlife, you’d rather not imagine yourself or your own children dead. Understandably, we all push the awareness of death back into the background of our minds. It’s still there, unconsciously affecting our thoughts, actions, and feelings, but remains unrecognised for the most part. Usually, it comes off as a constant unidentified anxiety and uneasiness.
In depression this anxiety is so extreme that you can barely go on with your life, but even the healthiest people aren’t completely free from it. Taking about death brings this creepy, unpleasant feeling back to the surface. That’s why talking about death at our Grand Meetup was so awkward and uncomfortable, and why we tried to turn it around with laughs.

The anxiety is always there, even if we don’t acknowledge it. And it drives our lives

Looking back, a lot of the things I did was at least partially motivated by trying to run away from this crippling fear and discomfort. Some of them were obviously unhealthy, like numbing myself with booze. In college I felt so miserable and unhappy, that I’d get completely wasted a few times a week, then spend the whole next day sick and hangover, then hate myself even more in result. I still wonder sometimes how I found my way out of this mess.
But even objectively good or neutral things can be sometimes used as a means to escape. Music, games, movies, TV series, magazines, sex, drugs, sports, fitness, dieting, shopping, work, social media, forums, blogs – even books, volunteering, religion, or spirituality, can all serve to push this anxiety further out of conscious awareness and reach. I’m not saying we shouldn’t do or enjoy any of these things. I’m just saying the true motives for doing them might be completely different from what we sincerely believe. Been there, done that, all of it.
If you can’t stand feeling bored, it might be the background underlying anxiety that you actually can’t stand.
If you pull out your phone every 5 minutes, it might be an attempt to keep your mind busy enough not to think about it.
If you pride yourself on being busy all the time, there might be some thoughts at the back of your mind you’d rather not entertain.
If you feel like you need to reset yourself every weekend, there might be some facts about yourself you’d prefer to forget.

If you feel like you’re always running away from something, thinking about death can help

You may prefer not to ponder upon your own mortality, and that’s perfectly fine. But if you’re tired of winning the 2048 game for the 2048th time, and of scrolling your Twitter feed back-and-forth for hours on end, this kind of practice can help you regain control of your life by putting things in perspective. Stoic philosophers of Ancient Rome recommended meditating upon death to maintain the right attitude while you’re still here on Earth. As Marcus Aurelius had it:
A trite but effective tactic against the fear of death: think of the list of people who had to be pried away from life. What did they gain by dying old? In the end, they all sleep six feet under—Caedicianus, Fabius, Julian, Lepidus, and all the rest. They buried their contemporaries, and were buried in turn. Our lifetime is so brief. And to live it out in these circumstances, among these people, in this body? Nothing to get excited about. Consider the abyss of time past, the infinite future. Three days of life or three generations: what’s the difference?
By confronting the fear of death heads on like Marcus Aurelius did, even if it feels unpleasant at times, we can free ourselves from its grip and do the things we truly want to do, rather than the things the fear might be driving us into.
Even if you don’t think of death in particular, but meditate consistently, the unidentified background anxiety will inevitably resurface to your conscious awareness. This happened to me a few months ago, and it felt like my whole life suddenly lost its meaning, with no hope of gaining it back. As trivial as it sounds right now, it was a fully-blown crisis back then, and knowing how lucky and privileged I am didn’t make it any easier on me.
However, as I stayed present with this feeling rather than running away from it like I’d previously do, I became more resilient, relaxed and effective than I ever was in my life. I still want to run away at times, and there’s many more layers of anxiety still left for me to peel, but this experience taught me to appreciate confronting difficult thoughts.
Actually, after I installed WeCroak, these awkward deadly reminders became quite an enjoyable break from whatever I considered extremely important at the given moment. Is it truly so important that I’d wish on my deathbed to do more of this?

Are you sure this goodbye is not the last one?

Automattic Grand Meetup is quite a unique setting. Some 700 folks from almost 70 countries gather in one place, most of whom had never talked in person before. Yet because our hiring process only selects people who really want to work here, and because we’re all constantly in touch on Slack and internal blogs, by the time we actually meet someone, we might be already friends with them for quite a long time. In fact, when it comes to peer relationships, we’re probably closer to a religious sect than to an average corporation.
My first GM was crazy overwhelming. This third one felt like a loving family reunion.
And as I sometimes have it with family reunions, when this year’s Grand Meetup was inevitably coming to an end, I became acutely aware of how I might be seeing some of the folks for the very last time. We jumped around on the dance floor, and I wondered how many of these folks from all corners of America, Australia or Asia will cross their paths again with mine. Even if we don’t split into several smaller meetups next year (which is still undecided), some of my friends might leave the company before I have a chance to see them again. Some other ones might move to different teams that meet on different continents at different times. And of course there’s always the possibility that either of us will get hit by a bus today. Or tomorrow. We’ll never know for sure.
It felt weird to think about this on a party. But it made me appreciate my friends even more. For these few precious hours, I made sure to enjoy and appreciate the time spent with them, and be fully present while they are still here with me. Scrolling my Twitter feed on the side suddenly could wait.
We’re all going to die anyway. Instead of freaking out, we might as well use it as a reminder to do what matters the most.

2 responses to “Don’t forget: you’re going to die – All the awkward shades of Automattic Grand Meetup”

  1. Death has been a pervasive reality for me in 2020, with the death of both my parents, and some pets. Being conscious of death doesn’t have to be morbid, and rather can let us be present in each moment.

    I had a conversation with someone today who recommended “The Tibetan Book of the Dead: Liberation Through Understanding in the Between”. Looking forward to giving that a read.

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