In it, I drew the distinction between “horizontally scaled” teams, in which physical offices are connected to remote workers via satellite (home or commercial) offices, and “fully distributed” teams where, as you said, “the creative center and soul of the organization on the internet, and not in an office.”
At Parse.ly, we’re only a couple years old but have been operating on the distributed team model, with ~13 fully distributed employees, and it’s working well. Always glad to hear stories about how Automattic has scaled it to 10X our size.
And, likewise, we blow some of our office space savings on camaraderie-building retreats; our most recent one was in New York, see [here] and [here.]
The prevailing idea before [Wladimir] Köppen was that ice ages occur when the earth’s tilt supercharges the wrath of cold winters. Köppen showed that wasn’t the case. Instead, moderately cool summers are the culprit.
It begins when a summer never gets warm enough to melt the previous winter’s snow. The leftover ice base makes it easier for snow to accumulate the following winter, which increases the odds of snow sticking around in the following summer, which attracts even more accumulation the following winter. Perpetual snow reflects more of the sun’s rays, which exacerbates cooling, which brings more snowfall, and on and on.
You start with a thin layer of snow left over from a cool summer that no one pays much attention to, and after a few tens of thousands of years the entire earth is covered in miles-thick ice.
Fascinating! The blog goes on to apply the idea to that strong base, accumulating a bit at a time, to investing and business. The power of compounding seems appropriate to share on the day Jeff Bezos announced his retirement.
I’ll leave you with one of my favorite quotes from Charlie Munger, which is also how the article ends:
Very excited to share the news that Revue is joining Twitter. I’m a huge fan of the idea of better newsletters and Automattic was the largest investor in Revue. I’m looking forward to seeing what the very talented team will do as part of the Twitter network. Also many thanks to Kevin Kelly and Om for introducing me to Revue early on.
I noticed a few people happy that some previous pages and files on the old site were returning 404 errors, like the controversial 1776 report, but on this I think the webmasters of the United States of America should demand better, since Cool URIs Don’t Change. Previous websites are all saved by the National Archives, but there doesn’t appear to be any sort of norm for automatically redirecting links that went to any subdirectories or addresses under WhiteHouse.gov.
There are WP plugins that could help, like Redirection, but also perhaps the root domain itself could always redirect to a subdomain, like 46.whitehouse.gov, so we’d have a consistent domain and permalinks for everything, and then each new administration would get a new subdomain.
I wanted to share with you all a short film I made with the help of Stephen Bollinger, with videos I made a few years ago on a photography trip to Iceland with Om and Mark. I hope it provides five minutes of serenity in your day.
I turn 37 today. I look around and I feel incredibly lucky to be writing this after a topsy-turvy year. I have health. I have friends whom I love. These are all good reasons to feel optimistic about the future. A few unconnected thoughts today:
My father had me when he was exactly 13,300 days old, and this year I passed that number of rotations of the Earth.
It’s hard to plan when so much is changing, so resolutions this year haven’t felt the same. But in times like these it’s even more important to plan for the long-term. A look back, once a year, is enough to remind of what remains.
I’m so thankful for the internet. It’s where I learned and practiced my trade. It’s where I connect every day with the most interesting and eclectic group of people I could imagine, a modern day Florence during the Renaissance. I hope to make a lot more internet and enable others to do the same.
Many years ago I said “Technology is best when it brings people together.” This quote has taken on a life of its own on motivational posters and images. When I first said it I think I had in mind WordCamps and meetups and other physical gatherings; this year it transformed for me seeing how technology brought together those separated by the pandemic. This year has appeared divisive, so it’s easy to overlook how many times people came together. It’s like the old saying, it’s not how many times you fall, it’s how many times you get up. Fall thirty-six times, get up thirty-seven.
Of all the smart home upgrades I’ve made, replacing all my regular smoke detectors with Nest Protects (Google’s smoke detector) has been the one that I regret the most.
I don’t really need a smart smoke detector. It doesn’t need to talk, connect to wifi, and cost hundreds of dollars. I don’t need it integrated with my Google account which is impossible to share, so I need to be personally involved to replace one.
But other smoke detectors are just so unsightly, and the Nest is light years ahead of the competition from a design standpoint.
There’s such an opportunity for something that looks as good as the Nest, but doesn’t require two-factor authentication to replace. I didn’t want to call it dumb but beautiful, so let’s say “autonomous and beautiful” appliances and home devices. I still want it to be smart, but if you’re going to have the risk profile of a device that connects to the internet, it needs to be worth it, like Brilliant, Sonos, smart TVs, or connected cameras.
I’m becoming more wary of any hardware that requires an app, just because of the natural decay of non-SaaS and non-open source software. Van Moof bikes are beautiful, but will they still connect well when iOS 24 is out and Bluetooth has been removed from iPhones for security reasons?
I recorded two interviews very far apart from each other, but which have surprisingly both come out today. The first is for one of my favorite sites on the web, Farnam Street. I was honored to be episode 100 on their Knowledge Project podcast. Knowledge Project is probably one of the podcasts I’ve listened to the most since it started. Please check out their other guests as well, they really do have the most interesting conversations with the most interesting folks.
Shane and I cover turnarounds, how environment affects performance, pros and cons of distributed work, uncovering your lacuna, mental models, and patterns of decision making.
On a completely different vein, I did a deep geek-out on technology and content management systems with Gina Trapani and Paul Ford, two of my favorite technologists, on the Postlight podcast. We covered a lot of tech history, my thoughts on Chromium and Mozilla’s Gecko engine, structured data, Gutenberg, and a lot more. If you’re a developer or a long-time WordPress community member you’ll enjoy this one, but it might be esoteric or technical if you’re not immersed in this world. Here’s a Spotify embed of the episode:
In both we do touch on my idea that, on a long enough timeline, the survival rate for all proprietary software drops to zero. (Hat tip to Fight Club.) Proprietary software is an evolutionary dead end. You can think of open source packages like genetic alleles that have a higher fitness function, and eventually become the fittest organism. The longer I spend watching mega-trends in technology, the more I see that pattern everywhere, from encyclopedias to cryptocurrencies.
Instead of sharing what’s in my backpack this year, I want to share the apps and pandemic purchases that were meaningful to me, along with a few words on each. Something I haven’t shared with you yet on this blog is… I went down a #vanlife rabbit hole and ended up camping and working remotely a decent chunk of the year. I learned a ton and feel much more resilient. So this is a phoneful and truckful update of my year.
First I’ll start with apps, these all link to Apple’s app store but almost all have Android equivalents that I also use:
Calm and Waking Up — Very different but both incredibly valuable meditation apps. I had an 82-day streak with Calm this year! I wouldn’t have survived without these.
Fitbod — You tell the app what equipment you have, how much time you have, and it gives you a workout like a trainer would, rotating muscle groups.
Streaks — An app for starting and tracking habits. This is a funny one because I actually stopped using it because it worked. The things I was tracking on Streaks became daily habits and I stopped using the app every day. The same thing happened for me with Zero, my daily fast became part of my routine so I’d only use Zero if I was doing a longer one.
Tumblr — It was so nice to have a social network centered around creativity and humor.
App I deleted and re-added the most: Twitter. I love the things I learn from using it, but hate feeling like I’m wasting time.
When on road trips I found Android Auto running off the Pixel 5 much more reliable than CarPlay, which would frequently freeze up on me. Things have improved with iOS 14, but I still always use the Pixel when I’m on a longer drive.
I also have been living with my Mom since July, including her two cats and new Coton du Tulear puppy. Pets are humbling! It’s been great to learn how to support them best, as I last lived with animals when I was in high school and wasn’t that conscious of the responsibility then.
Amazon says I made over 850 orders this year, more than double from any previous year. Here are the non-tech purchases that ended up having a big impact on me:
In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.
I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.
All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.
This tumultuous year, two things really helped me get through it: my colleagues at Automattic and the community of WordPress.
At the end of the year I usually deliver a speech to the WP community we call the State of the Word, that celebrates what we accomplished the previous year and shines a light on what we could focus on in the coming year. There’s always a great energy in the room and I love mixing with the audience before and after the talk. This year we did it online, which meant we could produce the talk a little more, and we made extra time for the Q&A afterward with answers not just from me but folks across the community.
One thing I’ll call out WordPress 5.6 had an all women and non-binary release squad of over 50 people, a first for WordPress and probably any large open source project. Also the market share of WordPress grew more in 2020 than it has in any year since it started being tracked!
If you’re curious about what’s next for WordPress, check it out:
This column is called Corner Office, and most people who choose to have offices are usually the bosses. And I’ve been to the offices of billionaire C.E.O.s that have their own private bathroom, beautiful art and couches. But these are all things that you can have in your house. What I love about distributed organizations is every single employee can have a corner office.
Sometimes my corner office has been the corner of an airport floor next to a power outlet! I’ve also heard from colleagues that feel like their office feels like an unsupervised day care center since the quarantine started. The point I want to make is there’s a world of possibility that opens up when you move from the finite space of a shared office, and all the politics of dividing up the scarce resource of desirable space, to the infinite game where people can define their own “office” as the place where they will be most productive, and do so however they like with no penalties or restraints.
If you had the best space in the legacy office, you probably liked it and may even have had motivated reasoning around ineffable things that happened in the office like “culture” that would be impossible without it, but the average experience of an entry-level worker was not as positive. Now there can be a much more even playing field. At Automattic we have a home office allowance people can use to buy equipment they need to make their home work area comfortable and productive, and it’s the same if you’re leading a team of hundreds or if it’s your first job.
Kathleen Morrison, in News & Views (“Failure and how to avoid it” Nature440, 752–754; 2006), notes that societies have often prevented collapse by adopting new technological strategies. In today’s world, where one of the most-talked about prospects for collapse is an epidemic of infectious disease, it is worth remembering that perhaps we already have the technological strategy to avoid it — the Internet.
Remote working, made possible by the Internet (‘telepresence’), is already a key component of national and business pandemic plans. Telepresence can inhibit viral transmission by reducing human-to-human contact. Prepared organizations can leverage telepresence to allow continued productivity and functioning of supply chains during an outbreak.
He explores these ideas as well in his Long Now talk in April 2010, in which he talked about Six Easy Steps to Avert the Collapse of Civilization. Here’s an excerpt from that talk covering telepresence and telemedicine. Both videos have had under a thousand views so far. When you watch this remember that it was April, 2010!
The quality improved, however something was still missing: I felt like I wasn’t connecting with the person on the other side. When I reviewed recordings, especially for major broadcasts, my eyes kept looking at the person on the screen rather than looking at the camera.
For normal video conferencing a setup this nice is a distraction, but if you’re running for political office during a quarantine, a public company CEO talking to colleagues and the press, here’s a cost-is-no-object CEO livestreaming kit you can set up pretty easily at home.
Basically what you do is put the A7r camera, shotgun mic, and the lens together and switch it to video mode, go to Setup 3, choose HDMI settings, and turn HDMI Info Display off — this gives you a “clean” video output from the camera. You can run off the built-in battery for a few hours, but the Gonine virtual battery above lets you power the camera indefinitely. Plug the HDMI from the camera to the USB Camlink, then plug that into your computer. Now you have the most beautiful webcam you’ve ever seen, and you can use the Camlink as both a video source and an audio source using the shotgun mic. Put the Key Light wherever it looks best. You’re fine to record something now.
If you’d like to have a more two-way conversation Interrotron style, set up the teleprompter on the tripod, put the camera behind it, connect the portable monitor to your computer (I did HMDI to a Mac Mini) and “mirror” your display to it. (You can also use an iPad and Sidecar for that.) Now you’ll have a reversed copy of your screen on the teleprompter mirror. I like to put the video of the person I’m talking to right over the lens, so near the bottom of my screen, and voilà! You now have great eye contact with the person you’re talking to. The only thing I haven’t been able to figure out is how to horizontally flip the screen in MacOS so all the text isn’t backward in the mirror reflection. For audio I usually just use a headset at this point, but if you want to not have a headset in the shot…
Use a discreet earbud. I love in-ear monitors from Ultimate Ears, so you can put one of these in and run the cable down the back of your shirt, and I use a little audio extender cable to easily reach the computer’s 3.5mm audio port. This is “extra” as the kids say and it may be tricky to get an ear molding taken during a pandemic. For the mic I use the audio feed from the Camlink, run through Krisp.ai if there is ambient noise, and it works great (except in the video above where it looks a few frames off and I can’t figure out why. On Zoom it seems totally normal).
Here’s what the setup looks like all put together:
After that photo was taken I got a Mac Mini mount and put the computer under the desk, which is much cleaner and quieter, but used this earlier photo so you could see everything plugged in. When you run this off a laptop its fan can get really loud.
Again, not the most practical for day to day meetings, but if you’re doing prominent remote streaming appearances—or if your child is an aspiring YouTube star—that’s how you can spend ~9k USD going all-out. You could drop about half the cost with only a minor drop in quality switching the camera and lens to a Sony RX100 VII and a small 3.5mm shotgun mic, and that’s probably what I’ll use if I ever start traveling again.
If I were to put together a livestreaming “hierarchy of needs,” it would be:
Solid internet connection (the most important thing, always)
The main feedback we got at the time was that the blogging software market was saturated and there wasn’t room or need for anything new.
WordPress did have a philosophy, an active blog, a license that protected the freedom of its users and developers, a love of typography, a belief that code is poetry, fantastic support forums and mailing lists and IRC, and firm sense that building software is more fun when you do it together as a community.
We have relentlessly iterated across 38 major releases since then, and here we are.
If you’d like to celebrate with me, put on some jazz, eat some BBQ, light a candle for the contributors who have passed on, help a friend or stranger less technical than you build a home online, and remember that technology is at its best when it brings people together.
On the distributed front, the future of work has been arriving quickly. This week, a wave of companies representing over $800B in market capitalization announced they’re embracing distributed work beyond what’s required by the pandemic:
The forces that enable working in a distributed fashion have been in motion for decades, and if you talk to anyone who was working in technology in the ’60s and ’70s they expected this to happen much sooner. Stephan Wolfram has been a remote CEO for 28 years. Automattic has been distributed-first for 15 years.
What’s been holding us back is fear of the unknown, and attachment to the familiar. I can’t tell you how many of the investors I see espousing distributed work once told me that Automattic would never scale past a few dozen people unless we brought everyone into an office. Or the CEOs who said this would never work for them, now proclaiming their company hasn’t missed a beat as tens of thousands of people started working from home.
What’s going to be newsworthy by the end of the year is not technology companies saying they’re embracing distributed work, but those that aren’t. Those who thought this couldn’t work have been forced by the pandemic to do it anyway, and they’ve now seen that it’s possible.
It was probably terrible at first, but now two or three months in it’s gotten better. We’ve learned and adapted, and will continue to do so. Necessity breeds invention. I promise you if you stick with it, you’ll progress through the levels of distributed autonomy. Over time people will be able to move houses, tweak furniture, buy equipment, upgrade their internet, and otherwise adapt to being more productive in a distributed environment than they ever could be in an office. Products and services are being developed all around the world that will make it even better. I’m so excited about how a majority of the economy going distributed will improve people’s quality of life, and unlock incredible creativity and innovation at work. (They go hand in hand.)
At some point, we’ll break bread with our colleagues again, and that will be glorious. I can’t wait. But along the way we’ll discover that things we thought were impossible were just hard at first, and got easier the more we did it. Some will return to physically co-working with strangers, and some employers trapped in the past will force people to go to offices, but the illusion that the office was about work will be shattered forever, and companies that hold on to that legacy will be replaced by companies who embrace the antifragile nature of distributed organizations.
Traditionally, cities looking to spur their economies may offer incentives to attract businesses. But at a time when Americans are moving less frequently than they have in more than half a century, and the anticlimactic race to host an Amazon HQ2 soured some governments on corporate tax breaks, Tulsa is one of several locales testing out a new premise: Pay people instead.
I love this idea, and hope that after the permanent step-up in remote work from the virus we see much more internal mobility between cities in the United States.
I recently had the opportunity to sit down with Sam Harris, author and host of the Making Sense podcast, for a wide-ranging conversation. Given the moment we’re currently living through, we naturally touched on the way companies are adapting to a new reality — one where remote work is a model to which they must adapt in a matter of days, rather than years.
As I mentioned to Sam on the podcast, “any company that can enable their people to be fully effective in a distributed fashion, can and should do it far beyond after this current crisis has passed.” It’s a moral imperative. But that doesn’t mean it’s going to be easy, or that the chaotic and stressful first taste some workplaces are getting right now is one that inspires them to keep trying.
To make sense of this journey — from a company’s cautious exploration of remote possibilities to a fully realized distributed experience — I like to think of how it plays out through the concept of levels of distributed work, which I modeled after self-driving car levels of autonomy. I’ve seen some solid recaps of my conversation with Sam from Steve Glaveski and Steve Jurvetson, but here’s my gist of how distributed companies evolve:
Level Zero autonomy is a job which cannot be done unless you’re physically there. Imagine construction worker, barista, massage therapist, firefighter… Many companies assumed they had far more of these than it has turned out they really did.
The first level is where most colocated businesses are: there’s no deliberate effort to make things remote-friendly, though in the case of many knowledge workers, people can keep things moving for a day or two when there’s an emergency. More often than not, they’ll likely put things off until they’re back in the office. Work happens on company equipment, in company space, on company time. You don’t have any special equipment and may have to use a clunky VPN to access basic work resources like email or your calendar. Larger level one companies often have people in the same building or campus dialing into a meeting. Level one companies were largely unprepared for this crisis.
Level two is where many companies have found themselves in the past few weeks with the COVID-19 pandemic. They’ve accepted that work is going to happen at home for a while, but they recreate what they were doing in the office in a “remote” setting, like Marshall McLuhan talked about new media mediums initially copying the generation before. You’re probably able to access information from afar, you’ve adapted to tools like Zoom or Microsoft Teams, but everything is still synchronous, your day is full of interruptions, no real-time meetings have been canceled (yet), and there’s a lot of anxiety in management around productivity — that’s the stage where companies sometimes install surveillance software on laptops. Pro tip: Don’t do that! And also: Don’t stop at level two!
At the third level, you’re really starting to benefit from being remote-first, or distributed. That’s when you see people invest in better equipment — from a good desk lamp to solid audio gear — and in more robust asynchronous processes that start to replace meetings. It’s also the point at which you realize just how crucial written communication is for your success, and you start looking for great writers in your hiring. When you are on a Zoom, you often also have a Google Doc up with the other meeting participants so you can take and check real-time notes together. Your company has a zero-trust BeyondCorp security model. In a non-pandemic world you plan meetups so teams can break bread and meet each other in person a week or two a year.
Level four is when things go truly asynchronous. You evaluate people’s work on what they produce, not how or when they produce it. Trust emerges as the glue that holds the entire operation together. You begin shifting to better — perhaps slower, but more deliberate — decision-making, and you empower everyone, not just the loudest or most extroverted, to weigh in on major conversations. You tap into the global talent pool, the 99% of the world’s population and intelligence that doesn’t live near one of your legacy physical office locations. Employee retention goes way up, and you invest more in training and coaching. Most employees have home-office setups that would make office workers green with envy. You have a rich social life with people you choose. Real-time meetings are respected and taken seriously, almost always have agendas and pre-work or post-work. If you get good at baton passes work will follow the sun 24/7 around the world. Your organization is truly inclusive because standards are objective and give people agency to accomplish their work their way.
Finally, I believe it’s always useful to have an ideal that’s not wholly attainable — and that’s level five, Nirvana! This is when you consistently perform better than any in-person organization could. You’re effortlessly effective. It’s when everyone in the company has time for wellness and mental health, when people bring their best selves and highest levels of creativity to do the best work of their careers, and just have fun. 🤠
A highly influential book for me in designing Automattic was Daniel Pink’s Drive, where he eloquently introduces the three things that really matter in motivating people: mastery, purpose, and autonomy. Mastery is the urge to get better skills. Purpose is the desire to do something that has meaning, that’s bigger than yourself. These first two principles physically co-located companies can be great at. But the third, autonomy, is where even the best in-office company can never match a Level 4 or above distributed company.
Autonomy is our desire to be self-directed, to have agency over ourselves and our environment. Close your eyes and imagine everything around you in a physical office: the chair you’re in, the desk, distance from a window, the smells, the temperature, the music, the flooring, what’s in the fridge, the comfort and privacy of the bathrooms, the people (or pets) around you, the lighting. Now imagine an environment where you can choose and control every one of those to your liking — maybe it’s a room in your house, a converted garage, a shared studio, or really anything, the important thing is you’re able to shape the environment fit your personal preferences, not the lowest common denominator of everyone an employer has decided to squish together for 8 hours a day. The micro-interactions of the hundreds of variables of your work environment can charge you and give you creative energy, or make you dependent, infantilized, and a character in someone else’s story. Which do you want to spend half of your waking workday hours in?