Reed Albergotti has a great article titled Latest Amenity for Startups: No Office. You can put in your email to read I believe but it's behind a paywall otherwise. The Information is a pretty excellent site that alongside (former Automattician) Ben Thompson's Stratechery I recommend subscribing to. Here are some quotes from the parts of the article that quote me or talk about Automattic:

So it’s no coincidence that one of the first companies to operate with a distributed workforce has roots in the open source movement. Automattic, the company behind open source software tools like WordPress, was founded in 2005 and has always allowed its employees to work from anywhere. The company’s 680 employees are based in 63 countries and speak 79 languages. Last year, it closed its San Francisco office, a converted warehouse — because so few employees were using it. It still has a few coworking spaces scattered around the globe.

Matt Mullenweg, Automattic’s founder and CEO, said that when the company first started, its employees communicated via IRC, an early form of instant messaging. Now it uses a whole host of software that’s tailor-made for remote work, and as the technology evolves, Automattic adopts what they need.

Mr. Mullenweg said Automattic only started having regular meetings, for instance, after it started using Zoom, a video conferencing tool that works even on slow internet connections.

He’s become a proponent of office-less companies and shares what he’s learned with other founders who are attempting it. Mr. Mullenweg said he believes the distributed approach has led to employees who are even more loyal to the company and that his employees especially appreciate that they don’t need to spend a chunk of their day on a commute.

“Our retention is off the charts,” he said.

And:

“Where it goes wrong is if they don’t have a strong network outside of work—they can become isolated and fall into bad habits,” Mr. Mullenweg said. He said he encourages employees to join groups, play sports and have friends outside of work. That kind of thing wouldn’t be a risk at big tech companies, where employees are encouraged to socialize and spend a lot of time with colleagues.

But for those who ask him about the negatives, Mr. Mullenweg offers anecdotal proof of a workaround.

For example, he said he has 14 employees in Seattle who wanted to beat the isolation by meeting up for work once a week. So they found a local bar that didn’t open until 5 p.m., pooled together the $250 per month co-working stipends that Automattic provides and convinced the bar’s owner to let them rent out the place every Friday.

They didn't need to pool all their co-working allowance to get the bar, I recall it was pretty cheap! Finally:

For Automattic, flying 700 employees to places like Whistler, British Columbia or Orlando, Florida, has turned into a seven-figure expense.

“I used to joke that we save it on office space and blow it on travel. But the reality is that in-person is really important. That’s a worthwhile investment,” Mr. Mullenweg said.It might take a while, but some people are convinced that a distributed workforce is the way of the future.

“Facebook is never going to work like this. Google is never going to work like this. But whatever replaces them will look more like a distributed company than a centralized one,” Mr. Mullenweg said.

Dean Allen, a web pioneer and good man, has passed away. I've been processing the news for a few days and still don't know where to begin. Dean was a writer, who wrote the software he wrote on. His websites were crafted, designed, and typeset so well you would have visited them even if they were filled with Lorem Ipsum, and paired with his writing you were drawn into an impossibly rich world. His blog was called Textism, and among many other things it introduced me to the art of typography.

Later, he created Textpattern, without which WordPress wouldn't exist. Later, he created Textdrive with Jason Hoffman, without which WordPress wouldn't have found an early business model or had a home on the web. He brought a care and craft to everything he touched that inspires me to this day. As John Gruber said, "Dean strove for perfection and often achieved it." (Aside: Making typography better on the web led John Gruber to release Smarty Pants, Dean a tool called Textile, and myself something called Texturize all within a few months of each other; John continued his work and created Markdown, I put Texturize into WP, and Dean released Textile in Textpattern.)

Years later, we became friends and shared many trips, walks, drinks, and meals together, often with Hanni and Om. (When we overlapped in Vancouver he immediately texted "I'll show you some butt-kicking food and drink.") His zest for life was matched with an encyclopedic knowledge of culture and voracious reading (and later podcast listening) habits. I learned so much in our time together, a web inspiration who turned for me into a real-life mensch. He was endlessly generous with his time and counsel in design, prose, and fashion. I learned the impossibly clever sentences he wrote, that you assumed were the product of a small writing crew or at least a few revisions, came annoyingly easily to him, an extension of how he actually thought and wrote and the culmination of a lifetime of telling stories and connecting to the human psyche.

Dean, who (of course) was also a great photographer, didn't love having his own photo taken but would occasionally tolerate me when I pointed a camera at him and Om has a number of the photos on his post. There's one that haunts me: before getting BBQ we were at his friend's apartment in Vancouver, listening to Mingus and enjoying hand-crafted old fashioneds with antique bitters, and despite the rain we went on the roof to see the art that was visible from there. He obliged to a photo this time though and we took photos of each other individually in front of a sign that said "EVERYTHING IS GOING TO BE ALRIGHT." It wasn't, but it's what I imagine Dean would say right now if he could.

I am very thankful and grateful to have made it through the past year, which was a really special one personally and professionally. I learned to open myself up more to relationships, continued aspiring to be clear and direct with yellow arrows, and worked alongside some incredible people to tackle the biggest and hardest problems, whether it was getting plugin and theme support on WP.com or the start and growth of Gutenberg.

I read a lot more books, traveled 337k miles between 91 cities, spent more time in Texas, kept my health in a good balance with weight training, running, and a better diet including several months of 16/8 intermittent fasting, while still getting in some excellent meals with friends and loved ones (up to 58% of top 50 list). As I'm solidly in my mid-thirties now, and I want to continue to live by: all things in moderation. I consider what I do with WordPress and Automattic my life's work, and hope to continue it as long as I'm useful. Some days I pinch myself.

Thank you to all of you on this journey with me. I am imperfect but trying my darndest, and I'm lucky to have friends and colleagues doing the same.

Previously: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, and 33.

Here's what I ended up reading this year, in roughly chronological finishing order. (I usually have 3-4 books going on at once.)

• Tools of Titans by Tim Ferriss.
• The Art of Stillness by Pico Ayer.
• Out of Your Mind by Alan Watts (audiobook, really a series of lectures).
• Book of Five Rings by Miyamoto Mushashi (audiobook).
• Do Not Say We Have Nothing by Madeleine Thien.
• The Best American Short Stories 2016 edited by Junot Diaz.
• Feynman by Jim Ottaviani.
• My Gita by Devdutt Pattanaik.
• From Plato to Post-modernism: Understanding the Essence of Literature and the Role of the Author by Louis Markos (another lecture series).
• The Rules Do Not Apply by Ariel Levy.
• The Story of a Brief Marriage by Anuk Arudpragasam.
• All the Light We Cannot See by Anthony Doerr.
• Ikigai: The Japanese Secret to a Long and Happy Life by Héctor García and Francesc Miralles.
• When Hitler Took Cocaine and Lenin Lost His Brain: History's Unknown Chapters by Giles Milton.
• Widow Basquiat: A Love Story by Jennifer Clement.
• 32 Yolks: From My Mother's Table to Working the Line by Eric Ripert.
• Identify: Basic Principles of Identity Design in the Iconic Trademarks by Chermayeff & Geismar.
• Catching the Big Fish: Meditation, Consciousness, and Creativity by David Lynch (audiobook).
• The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World by Brad Stone.
• The Leavers by Lisa Ko.
• Wolf Hall by Hilary Mantel.
• Girls on Fire by Robin Wasserman.
• The Executive's Compass by James O'Toole.
• Tuesdays with Morrie by Mitch Albom.
• Dance of the Possible by Scott Berkun.
• The Lifecycle of Software Objects by Ted Chiang (short story).
• Tribe of Mentors by Tim Ferriss.
• After On: A Novel of Silicon Valley by Rob Reid.
• Principles by Ray Dalio.
• The Graveyard Book by Neil Gaiman (audiobook).
• The Undiscovered Self: With Symbols and the Interpretation of Dreams by C.G. Jung.

A fairly random selection, and hopefully I can get a few more in next year.

James Beshara has a really interesting read on how communication will change and evolve in a post-verbal world, namely one where human/brain interfaces like Neuralink can more directly transmit thought between people than the medium of language allows today.

After reading the essay I wonder if people's thoughts or the neural pathways they activate, if they could be directly transmitted into another brain, would actually make any sense to someone else with a unique internal set of pathways and framework for parsing and understanding the world. The essay assumes we'd understand and have more empathy with each other, but that seems like a leap. It seems likely the neural link would need it own set of abstractions, perhaps even unique per person, similar to how Google Translate AI invented its own meta-language.

Today idea-viruses that cause outrage (outrageous?) in today's discourse  have been weaponized by algorithms optimizing for engagement, and directly brain-transmitted memes seem especially risky for appealing to our base natures or causing amygdala hijack. But perhaps a feature of these neural interface devices could counteract that, with a command like "tell me this piece of news but suppress my confirmation bias and tribal emotional reactions while I'm taking it in."

This is a long quote/excerpt from Adam Robinson I’ve been holding onto for a while, from Tribe of Mentors. Worth considering, especially if you strive to work in a data-informed product organization.

Virtually all investors have been told when they were younger — or implicitly believe, or have been tacitly encouraged to do so by the cookie-cutter curriculums of the business schools they all attend — that the more they understand the world, the better their investment results. It makes sense, doesn’t it? The more information we acquire and evaluate, the “better informed” we become, the better our decisions. Accumulating information, becoming “better informed,” is certainly an advantage in numerous, if not most, fields.

But not in the eld of counterintuitive world of investing, where accumulating information can hurt your investment results.

In 1974, Paul Slovic — a world-class psychologist, and a peer of Nobel laureate Daniel Kahneman — decided to evaluate the effect of information on decision-making. This study should be taught at every business school in the country. Slovic gathered eight professional horse handicappers and announced, “I want to see how well you predict the winners of horse races.” Now, these handicappers were all seasoned professionals who made their livings solely on their gambling skills.

Slovic told them the test would consist of predicting 40 horse races in four consecutive rounds. In the first round, each gambler would be given the five pieces of information he wanted on each horse, which would vary from handicapper to handicapper. One handicapper might want the years of experience the jockey had as one of his top five variables, while another might not care about that at all but want the fastest speed any given horse had achieved in the past year, or whatever.

Finally, in addition to asking the handicappers to predict the winner of each race, he asked each one also to state how confident he was in his prediction. Now, as it turns out, there were an average of ten horses in each race, so we would expect by blind chance — random guessing — each handicapper would be right 10 percent of the time, and that their confidence with a blind guess to be 10 percent.

So in round one, with just five pieces of information, the handicappers were 17 percent accurate, which is pretty good, 70 percent better than the 10 percent chance they started with when given zero pieces of information. And interestingly, their confidence was 19 percent — almost exactly as confident as they should have been. They were 17 percent accurate and 19 percent confident in their predictions.

In round two, they were given ten pieces of information. In round three, 20 pieces of information. And in the fourth and final round, 40 pieces of information. That’s a whole lot more than the five pieces of information they started with. Surprisingly, their accuracy had flatlined at 17 percent; they were no more accurate with the additional 35 pieces of information. Unfortunately, their confidence nearly doubled — to 34 percent! So the additional information made them no more accurate but a whole lot more confident. Which would have led them to increase the size of their bets and lose money as a result.

Beyond a certain minimum amount, additional information only feeds — leaving aside the considerable cost of and delay occasioned in acquiring it — what psychologists call “confirmation bias.” The information we gain that conflicts with our original assessment or conclusion, we conveniently ignore or dismiss, while the information that confirms our original decision makes us increasingly certain that our conclusion was correct.

So, to return to investing, the second problem with trying to understand the world is that it is simply far too complex to grasp, and the more dogged our at- tempts to understand the world, the more we earnestly want to “explain” events and trends in it, the more we become attached to our resulting beliefs — which are always more or less mistaken — blinding us to the financial trends that are actually unfolding. Worse, we think we understand the world, giving investors a false sense of confidence, when in fact we always more or less misunderstand it.
You hear it all the time from even the most seasoned investors and financial “experts” that this trend or that “doesn’t make sense.” “It doesn’t make sense that the dollar keeps going lower” or “it makes no sense that stocks keep going higher.” But what’s really going on when investors say that something makes no sense is that they have a dozen or whatever reasons why the trend should be moving in the opposite direction.. yet it keeps moving in the current direction. So they believe the trend makes no sense. But what makes no sense is their model of the world. That’s what doesn’t make sense. The world always makes sense.

In fact, because financial trends involve human behavior and human beliefs on a global scale, the most powerful trends won’t make sense until it becomes too late to profit from them. By the time investors formulate an understanding that gives them the confidence to invest, the investment opportunity has already passed.

So when I hear sophisticated investors or financial commentators say, for example, that it makes no sense how energy stocks keep going lower, I know that energy stocks have a lot lower to go. Because all those investors are on the wrong side of the trade, in denial, probably doubling down on their original decision to buy energy stocks. Eventually they will throw in the towel and have to sell those energy stocks, driving prices lower still.