Here are the best online articles and blog posts I read in 2020. For each one I’ve provided a short excerpt and an explanation of how it shaped my thinking.

#1 Seeing Like an Algorithm

“Understanding how the algorithm achieves its accuracy matters even if you’re not interested in TikTok or the short video space because more and more, companies in all industries will be running up against a competitor whose advantage centers around a machine learning algorithm.”

This piece by Eugene Wei was the most insightful thing I read this year explaining the meteoric rise of the social video-sharing app TikTok. It explains why the vaunted “algorithm” that powers TikTok’s recommendations is so powerful, but also how the overall design of the platform makes that algorithm possible in the first place. It’s a more nuanced take than most I’ve seen online, and also sheds light on a future where all kinds of companies will use mysterious algorithms as their secret sauce.

#2 There and back again: the story of renaming ConvertKit

“As I spoke I could see the other panelists faces change. They didn’t know the story and looked more and more concerned, shocked, and then horrified as I detailed how we had naively appropriated a sacred word from another culture and used it to name our marketing company. While it hadn’t been intentional, we had still misstepped in a major way, and taken something from another culture that wasn’t ours. But we learned from our mistake, apologized, and moved away from it.”

This is a story told by Nathan Barry, Founder and CEO of the email marketing platform ConvertKit (which I use), about how his team chose a new name to rebrand their company. Along with the wrenching process of walking back that name change when they realized it was appropriating a sacred word from a foreign culture. In a time when people are being publicly shamed and cancelled, and everything seems black or white, this is a more complex story of what it looks like when a company that cares about its values recognizes its mistake and changes course.

#3 Four Editors in Search of a Thread: A Documentary Roundtable

“The task of the documentary editor is not simply to tell a story, but more often to find that story, embedded in a enormous mass of material that initially seems to have no structure at all.”

This article is an abridged transcript of an interview by Andrea Van Hook with four of the top documentary filmmakers of our generation. You may have noticed I’ve been obsessed with documentary filmmaking over the past year, and this is one of the most insightful sources I’ve found on the topic. As the quote above illustrates, there is a parallel between the job of a film editor and a note-taker: to make meaning out of a morass of raw material.

#4 It Takes a Community: The Story Behind Circle

“Above all, we loved the idea of empowering creators by helping them build clean, distraction-free, non-toxic communities that prompted loyalty from their members, and open up monetizable opportunities for them like memberships.”

Community and connection is at the heart of everything we do, so it was a big decision to move our online community wholesale from Discourse to Circle in early 2020. Until now, private Facebook groups have been the norm for online courses. Discourse is a highly customizable, open source alternative, but was far too complicated for users and staff alike. With Circle, you can now provide a world-class experience without sacrificing your direct relationship with your customers. Founder Sid Yadav tells the story of their first year in business in this post.

#5 Announcing the next Substack Fellowship for Independent Writers

“We’re excited about a future where writers of all backgrounds can pursue the work they find most meaningful, free of gatekeepers, and independent of what’s trending, and we’re eager to make it accessible to even more writers.”

In 2020 the newsletter publishing service Substack launched the second round of their writer’s fellowship. I realized that I had a platform that could do something similar: accelerate the careers of up-and-coming, promising writers. I would focus on writers in the productivity and personal effectiveness arena, which is what my audience is most interested in hearing. This article by Fiona Monga inspired me to start the Praxis Fellowship, in which we are supporting three promising writers in publishing their ideas to the world.

#6 Why MasterClass Isn’t Really About Mastery

“I actually think this is what massive online open courses (MOOCs) got wrong. They have notoriously low completion rates (around 5%), which is generally cited as the reason they didn’t upend the education system. But I think their mistake wasn’t in that people weren’t finishing the courses. Instead, it was the thesis that online, low-touch courses were for skill-building instead of inspiration or entertainment. Maybe if companies like Coursera and Udemy would’ve leaned into edutainment instead of job preparation it could’ve been a different story.”

The quote above was in parentheses as an aside, but I found it to be the most insightful takeaway from this piece by Adam Keesling: the wave of MOOCs (Massive Open Online Courses) over the last couple decades have been criticized for their low completion rates, but that wasn’t the real issue. The real problem is that they tried to impart skill-building, which is very difficult to do without feedback and interaction with an instructor and peers. Instead, self-paced content is best used for inspiration and entertainment, sometimes known as “edutainment,” which are no less important for learning despite not being as glamorous. Cohort-Based Courses, which is the model we use, are far better suited for training people in new skills.

#7 After Postmodernism: Eleven Metamodern Methods in the Arts

“Something seemed to have changed in the new millennium that made it cool again to express unabashed feelings — joy, wonder, sadness, vulnerability, triumph — in our art, and in everyday life, unfettered by the ever-present ironic snark that controlled the nineties and earlier… somehow, in such a way that didn’t toss out the fun that could be had in playing with irony.”

This year I was introduced to Metamodernism, the tentative name for the current wave of culture that combines the conviction of modernism with the relativity of postmodernism, with an emphasis on the felt experience of living. The piece What is Metamodernism?, written by Greg Dember and Linda Ceriello, explains what metamodernism is, and this one dives deeper into its main facets, which include:

  • Meta-reflexivity (“Life as Movie”)
  • The narrative double frame (Eshelman’s Performatism)
  • Oscillation between opposites
  • Quirky
  • The Tiny (metamodern minimalism)
  • The Epic (metamodern maximalism)
  • Constructive Pastiche
  • Ironesty
  • Normcore
  • Overprojection (Anthropomorphizing)
  • Meta-Cute

I don’t usually get into discussions of abstract cultural movements, but in this writing I saw a lot of my own attitudes toward the work I do. My father always talks about how powerfully modernism shaped his thinking, and I was raised in the decades shaped by postmodernism. I think metamodernism could be a new middle path that combines some of the best parts of earlier eras, ultimately allowing more kinds of meaningful creative expression.

#8 The Coronavirus Is Rewriting Our Imaginations

“The virus is rewriting our imaginations. What felt impossible has become thinkable. We’re getting a different sense of our place in history. We know we’re entering a new world, a new era. We seem to be learning our way into a new structure of feeling.”

Kim Stanley Robinson is one of my favorite science-fiction writers. His Mars Trilogy is, in my opinion, one of the greatest feats of future speculation ever achieved. The work he’s done to envision the finest details of mankind’s future give him extra credibility in examining the current pandemic. In this piece Robinson draws some profound parallels between what the coronavirus is teaching us, and what will be needed to tackle the climate change crisis in coming years. Beyond the tangible impact on our health and the economy, COVID-19 is rewriting how our imaginations work.

#9 The Web and the New Reality

“…we march into the Information Age hobbled by industrial metaphors. The ‘information highway’ is one example. Here we use the language of freight forwarding to describe the movement of music, love, gossip, jokes, ideas and other communicable forms of knowledge that grow and change as they move from mind to mind.”

This remarkable blog post by Doc Searls was first published in 1995, more than a quarter century ago now. It might as well have been written yesterday. It ranges across a variety of topics related to the momentous transition from an industrial to a digital economy, which has only picked up speed all these years later. It’s up to all of us to navigate these changes and decide what they mean for us, then and now.

#10 Bundle Magic

“…custom pricing is not always possible. Spotify doesn’t have time to negotiate with you. In those cases, bundles can be a great way to solve this problem. By offering a bundle instead of an individual purchase, you change the shape of the demand curve in such a way that it’s flatter, and there is less deadweight loss.”

This piece by Nathan Baschez unlocked a few important things for me. The concept of “bundling” is one of the most widespread business models on the Internet, yet it’s not well understood from the consumer’s perspective. In particular, Nathan’s piece helped me see how my online courses are bundles (as I explained in this Twitter thread), and what I can do to make educational bundles more attractive. It also inspired me to join the bundle that Nathan runs along with Dan Shipper, called Everything.

#11 Bibliologistics: The Nature of Books Now, or A Memorable Fancy

“Drawing on a recent complex of disciplinary engagements in infrastructure and logistics — which themselves draw on media studies, the environmental humanities, postcolonial theory, transnational geography, security studies, and more — this essay instead proposes a combination of network analysis and site-specific research I call bibliologistics.”

Books have now become virtual objects, abstracted from ink and paper into a web of digital connections spanning the globe. In this piece, Matthew Kirschenbaum traces the path of a single printed book through global supply chains as a way of understanding what it means to “publish” a book today. It’s a fascinating look into the system of global knowledge production that so many of us are part of today.

#12 Premonition

“Which of my beliefs remain unchanged? What assumptions will remain in place? What trends will be accelerated, which delayed, and which stopped entirely? What do I care about that has become newly relevant, and what no longer matters?”

This is a collection of trend predictions put together by Toby Shorin, gathered from his friends and network. It includes some striking ideas about how the coronavirus pandemic specifically and the vast cultural shifts it has accelerated in general will play out in the coming years, including implications for culture, brands, space, entertainment, tools and platforms, politics, and death. I don’t usually put much stock in trend forecasts, but these ones have an unusual amount of thought behind them.

#13 Can a School Have Product-Market Fit?

“I’ve worked with many schools and bootcamps over the last decade, and one of the things that has surprised me is that none of them have product-market fit.”

This newsletter by Brian Tobal may seem very niche, but it has significant implications for how online education will play out. His basic argument is that a single course can have product-market fit, by providing a reliable pathway for a student to get a good job for example. But once that course expands into a broader curriculum of courses (which make up a “school”), it’s not possible for that larger entity to have product-market fit because it serves multiple kinds of customers with multiple needs.

As I described in my year-end review, we’ve discovered this for ourselves, as our efforts to expand our roster of courses were met with frustration. On the Internet, the most relevant unit of education isn’t the school, as it is in the physical world. The most relevant entity is the course, and I think we’re going to see courses grow in scale, profitability, and brand recognition to eclipse even the online schools that host them. Which also means that individual instructors who create successful courses will have most of the power (and profits) in the online education industry.

#14 Digital Theme Park Platforms: The Most Important Media Businesses of the Future

“…the most important distinction between physical and digital theme parks isn’t the hours of operation, infinite capacity, or ability to disregard the second law of thermodynamics. Instead, it’s that these parks were designed to (or have since been converted to) allow for anyone to be an “Imagineer”. The developers of these titles aren’t trying to make a “game” but a “game engine” that allows everyone to create and share their own attraction.”

This piece powerfully shaped my thinking on the future of our business (and the media industry generally) this past year. Matthew Ball uses Disney as an example of how multiple kinds of media can work together to create something much greater than the sum of its parts. Kids can get to know a character in a Disney movie, buy Disney merchandise to play that character, go to Disneyland to interact with them, etc.

Sometimes I wonder whether I should pursue so many different kinds of content and products, from written pieces to YouTube videos to online courses to subscriptions. I want to keep the company small, so it might seem like a better idea to focus on just one or two channels and polish them to perfection.

But I’ve since realized that what I’m building is actually a “digital theme park.” It is a platform, but a platform where the participants create the content and experiences. This is not only a lot more fun, it gives them a sense of personal investment and shared ownership that is better for them (makes the ideas sink in more deeply) and better for us (generates more loyalty). It’s difficult to create this kind of 360-degree interaction if you’re limited to only one kind of media in one channel.

I see Forte Labs as an “extended universe” with many entry points, and once you’re inside, many ways of creating, discussing, learning, and interacting. There isn’t one linear “customer journey” through it all. There is a multi-layered community where the distinction between “consumer” and “creator” is blurred, just like I’m trying to encourage them to do in real life.

#15 Starting Up The Start-Up of You: Lessons Learned and Personal Reflections on Publishing a Bestselling Business Book

“…the most significant benefit of starting with a book was one we didn’t fully appreciate at the outset: a book’s linear, static format, and the expectations around the length and detail and substance of what’s inside of a book, collectively force upon the creative process a rigor unmatched in other mediums…Attempting to write a book forced us to be super precise and thoughtful about what we wanted to say. And of course, once you have precise thoughts, then it’s comparatively easy to disseminate them in various channels and formats.”

This is an account by Ben Casnocha of his experience conceiving, planning, writing, editing, publishing, and selling The Start-Up Of You, which he co-wrote with Reid Hoffman. It was published in 2012, but the hindsight provides some helpful perspective that is still just as valid today.

This piece makes the most succinct argument I’ve seen as to why it’s still worth publishing a book in print today. As the quote above points out, the length and depth (and permanence) of a book act as forcing functions to demand a far greater level of rigor than you would put into something digital like a blog post or even an ebook. And the rigor of the thinking that goes into a book is the single biggest factor in its success. I also really liked how Ben and Reid thought about the book as a product, which had to be designed and marketed and distributed just like any other product from a new startup. That’s exactly how I think about the book I’m writing.

#16 1,000 True Fans? Try 100

“As the Passion Economy grows, more people are monetizing what they love. The global adoption of social platforms like Facebook and YouTube, the mainstreaming of the influencer model, and the rise of new creator tools has shifted the threshold for success. I believe that creators need to amass only 100 True Fans—not 1,000—paying them $1,000 a year, not $100. Today, creators can effectively make more money off fewer fans.”

I loved seeing this piece by Li Jin, on one of the most underappreciated implications of the new wave of “creator” platforms: it is now possible to make more money from fewer followers, which means the “online creator” career path is open to more people than ever before. Jin riffs off the Internet classic 1,000 True Fans by Kevin Kelly, to go a step further and argue that it is now possible to make a living from only 100 die-hard fans.

The most viable way to do that, in my opinion, is through Cohort-Based Courses like the ones we teach. Teaching a course in a highly interactive, community-based way gives instructors and students alike the benefits of teaching (scalability, structure), consulting (high-end experience, customization), and coaching (accountability, long-term relationship) all at once. I’d love to see “being a creator” continue growing from a tiny niche to a mainstream lifestyle.

#17 Starlink is a Big Deal

“Starlink satellites are the solution, at only a 550 kilometer altitude. Going much faster due to the lower orbit, they’re not going to stay put, viewed from the ground: you’re not going to be aiming a dish at them. There are also going to be a lot of them, which is why this project wasn’t feasible until the previous milestone of “cheap access to orbit” was checked off. Thanks to the hard work of SpaceX to make cheap, reusable rockets an everyday reality, now a project of this scale and ambition is finally realistic.”

This excellent article by Jeffrey Paul lays out the case for Starlink, a new global, satellite-based Internet network being launched by Elon Musk’s SpaceX. It does such a good job of explaining how the technical details of the Starlink network have world-changing implications far beyond what’s visible on the surface. It delves into how reliable, worldwide connectivity will change so many aspects of how our cities are designed and our jobs distributed. I think Starlink is one of the least appreciated, almost hidden technological changes that is about to rock our world.

#18 Systemics and design principles in support of Tiago Forte’s PARA framework

“The key lesson here is in how pace layers and the panarchy structure align to inform how we should be managing the materials of our work. These concepts re-emphasize the notion that Projects should be fast-moving while Areas move slower and Resources and Archives move slowest of all. They also reinforce the idea that these areas inform one another. Slower layers set boundaries on what can happen on faster layers; layers higher in the panarchy depend on the learning and innovation on lower levels.”

I couldn’t help but include this piece, written by designer Ryan Murphy, in support of my organizing system PARA. Unlike most content I see that might reexplain PARA in an author’s own words, Murphy did something more fundamental: he showed how PARA made use of well-known design principles such as “pace layers” and “panarchy.” I’m always amazed how common sense methods discovered through everyday working often end up being aligned with deep principles.

#19 How to read self-help

We’re embarrassed by self-help, but we’re also attracted to it. We like reading it, but we’re skeptical that it works. We suspect self-help isn’t useful, but every serious list of business books turns out to be comprised entirely of self-help books.”

I loved this piece by Tom Cleveland for its balanced approach to self-help, which is all too rare. Critics usually either unfairly cast all self-help as scammy and empty, or embrace one particular book or method as a panacea. Cleveland instead describes a spectrum of self-help, from empty calories to nutritious feasts. What matters most is actually the attitude and mindset that you take on when you approach any kind of life advice. You have to decide what’s right for you, and how you’re going to incorporate it into your thinking and life. But that’s a lot harder than casually dismissing or mindlessly embracing the next bestselling book you see in the airport bookstore.

#20 The Internet of Beefs

“The Internet of Beefs, or IoB, is everywhere, on all platforms, all the time. Meatspace is just a source of matériel to be deployed online, possibly after some tasteful editing, decontextualization, and now AI-assisted manipulation. If you participate in online public life, you cannot entirely avoid the Internet of Beefs. It is too big, too ubiquitous, and too widely distributed and connected across platforms. To continue operating in public spaces without being drawn into the conflict, you have to build an arsenal of passive-aggressive behaviors like subtweeting, ghosting, blocking, and muting — all while ignoring beef-only thinkers calling you out furiously as dishonorable and cowardly, and trying to bait you into active aggression.”

In one of the most strikingly insightful reads of the year, Venkatesh Rao introduced a term that I think perfectly encapsulates what much of the Internet has become: an Internet of Beefs (as in, grudges or fights between people). He brings this simmering reality to the surface, calling out “Knights” (celebrities and pseudo-celebrities declaring war on behalf of their cause) and “Mooks” (anonymous foot soldiers doing most of the real fighting on the Knights’ behalf).

Rao entertainingly describes the quasi-feudal structure that many conversations on the Internet have taken on, with countless micro-battles between hordes of mooks playing out across every corner of the Internet. I loved seeing how far this analogy goes, and how it frames what is possible and what isn’t possible when we engage with strangers online.


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