Town Square, Guilds, and Community

June 15, 2022
15 min read
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It felt like a gold rush was happening on the internet in 2010. It was a timely moment to start a blog, build an audience, or create a services business. But like many prospectors in the gold rush of 1848, I was a little late and under-equipped.

Especially for my generation of creatives, it was a unique time in our internet history for design (products and graphics) and words (blogs, newsletters, editorial, etc.).

No one in my university or close circles saw what I was seeing:

  • Blogging was the thing.
  • Bloggers were amassing 100k+ subscribers, selling thousands of eBooks, and eventually getting speaking gigs, books deals, etc.
  • The path seemed straightforward (but not easy): Build a popular blog around a niche topic (blogging about blogging), grow your audience, leverage it up to write for known publications, get those mastheads in your bio, get a book deal, pursue blogging full-time, speak at TED, publish another book, become a best-seller, quit your job, sell a course, start a podcast.
  • Webinars were hot, and content marketers could bring in anywhere from 100 to 1,000 people (then they shill a $99 content marketing course; a re-bundle of, say, 20 blog posts repackaged).
  • Twitter was a place to share links and allowed only 140 characters.
  • Entrepreneurs were obsessed with quoting Sun Tzu and Dale Carnegie. 

If you were in it during this time, these names may sound familiar: 99u, Copyblogger, Problogger, Zenhabits, Tiny Buddha, Write to Done, Dumb Little Man. If you were early in being a “content marketer” these were the places to publish. A blog post with 100 comments? Major. One guest post would yield thousands of new visitors because people actually clicked the link in your byline. If you showed up consistently in these places, you would see familiar names in your comment section. 

I couldn’t look to traditional education for guidance because my professors didn’t care about what I was seeing. None of my friends were trying to build a creative career. People didn’t take blogs or blogging seriously. In the movie Contagion, one of the characters nailed blogging’s place in culture at the time when he called it “graffiti with punctuation.” Instead I found a community of like-minded learners and relevant knowledge online. Comment sections on blogs were enriching; people discussed ideas and offered practical knowledge. I took workshops with established or “popular” bloggers on how to build a blog, pitch publications, grow an audience, grow a newsletter, write “compelling” blog posts, write landing pages, sell products, etc.

All of this was a better experience than college because I was building a portfolio and learning from industry pros, and I had skin in the game. When I met Seth Godin in 2012 for a three-day workshop, his worldview about the future of work, how to build a life around a portfolio of projects, and where writing could take someone provided the kind of context and clarity that shaped the life I lead today. 

All I needed was an example to point at and say, “See? This!” Because no one in my close circles understood what I was seeing. “Writing?” they asked. “How do you make money?” But deep down I knew that the path I wanted to go on would be something important in the future. Hope and self-delusion is vital in these formative years.

Eventually, I got real with myself and treated my blog as a side project. It was good practice, but I had to make money and gain life experience. Blogging about blogging was overcrowded. I got a job as a content marketer at a start-up making way more money than most of my peers. And it was remote. My blog, portfolio, and side-projects landed me a job instantly. And the hiring manager didn’t ask where I went to school or for my GPA. 

I sometimes wonder if my career path would be vastly different if this feeling of an online town square wasn’t around during my formative years. I looked at these publications as hubs of knowledge. Reading stories about people who weren't born artists or had parents that worked in the arts gave me hope that a brute like me could actually become something more. There was discovery of new ideas and writers. I was malleable. Hungry for knowledge. Anything could have swayed me.

If someone I admired told me to be a coder, I would have done it. Instead I discovered people like Seth Godin, Maria Popova, and Tim Ferris. I was amazed that people were building careers like this — with words, storytelling, and sharing ideas. I felt lucky to be around this rising culture of creating cohesive, relevant ideas, lessons learned, and an inside look into worlds that felt distant for this first-generation Korean American living in New Jersey. 

The Creative Town Square

Remedios Varo The Juggler (The Magician) 1956 via The MoMA

I miss this moment in time. I yearn for it. I wonder what happened to it.

What happened to me? Did my naivety wash away? Did I outgrow all of it? Are people reading anymore or are we all just watching videos on different screens?

And most of all, what are people doing today? Where is their version of a town square?

Publications like 99u commanded the largest creative and entrepreneurial audience during these early years. If you were in the game as an artist, a creative, freelancer or entrepreneur, you probably devoured content from 99u, Its Nice That, CreativeMornings, AIGA, Design Matters, Print Magazine, The Dieline, The Great Discontent, TED, The School of Life, and took Skillshare or CreativeLive classes on the weekend. 

This was where the real makers were sharing spicy opinions and lessons learned. You had a front row seat to experiences that were only shared in closed circles or major cities. Where young creatives could become aware of new artists and startups or latest trends and buzzwords. It was some of the sharpest writing on the creative industry, on creativity, and life in between. Publications like these lowered barriers and democratized knowledge so that anyone wanting to build a creative life could. (Shoutout to my friends who served as the editors that made it what it was.)

I was invited to the beta of Medium, too (thank you Paul Jarvis!). For a year, it felt like a magical community of writers from all edges of the world. The design was slick (woah, no sidebar!). The genuine enthusiasm in the comments pulled on heartstrings and got writers to come back (remember the burrito story?). Ev Williams commented on an article telling me about a typo. The gift was instant access to a hungry audience of curious readers who, if you did good, would share your articles on Twitter and Facebook. This was the golden time to build an audience fast. But like anything fresh and reserved for a small group of people, once it opens up to the masses, it changes. Then people turned it into a secondary publishing home after their blog. It became pedantic and easy to ignore because it didn't feel fresh anymore.

Social media was different, too. Twitter was where people mostly shared links — articles, TED talks, spiritual quotes, entrepreneur quotes, interesting websites found on StumbleUpon or Tumblr. I talked about these ideas with friends over text or in-person. There were no threads or dunking on others, and there was hardly the level of shitposting you see today. It didn’t become the new News source. It quickly went from a game of sharing knowledge to a status game.

It felt like everyone had a blog or a newsletter (people can say that today, but I’m saying this was the reality 12 years ago). Everyone was watching TED talks and commencement speeches and Steve Jobs presentations. Talked about the same frameworks: “Jobs to be done”; “MVPs”; “Lean start-ups”; “Content is king”; “Build your personal brand.” 

Turns out, this cultural moment was the rise of the How To Movement (this podcast with Jay Acunzo on “Leaving Expertville” paints this moment in time perfectly). Nearly every blog I read or self-published books from bloggers focused on how to do something: how to build a business, how to build a blog, how to grow an audience, how to write well, how to start an agency, how to grow a newsletter, how to sell digital products, how to become a blogger, how to become a design-thinker. 

The internet needed time for people to copy-and-paste information from the physical world into our new digital world.

This was, frankly, the last golden era of reading. People loved to devour how-to knowledge, and if you can position yourself as an expert, you can build a thriving business. People were reading, not watching videos like today. Because I was the customer, the audience — a young, mid-twenty something writer looking to build a career on the internet — I was also their best promoter.

In this tiny pocket of the internet, there were marketers, writers, and advertising folk who had experience. But for so long, the knowledge was kept in their heads or within the walls of the workplace. With the rise of the Information Age and people’s desire to build personal brands, they were converting their experiences and ideas to fit into this new digital landscape, reaching far more people than they ever could before. Young, naive writers like me ate up everything these people said — because the only alternative, which felt insufficient, was traditional education and old textbooks. Direct access to expertise and earned wisdom was the bridge that the internet enabled.

Nearly every publication I read from those days are still around, but they feel like abandoned towns in an old Western. The goldmine ran out of gold. Only the echoes of latecomers remain.

Most of them sold their businesses and retired or started podcasts or built new projects. Others focused on a smaller niche and no longer have to play the game of building an audience.

The new class uses similar marketing tactics and styles on Twitter/LinkedIn like the OGs of pre-2010. I can’t help but roll my eyes when I see a thread on Twitter with thousands of retweets talking about how to give/receive feedback (my article on Lifehacker published in 2015) or how to make career decisions. There will always be an audience that engages with it — like me early on. It sounds like cover songs but in different venues. 

It is also the realization that I am not that audience anymore.

It is also, if I am to be real with myself, envy. I wish I wasn’t so self-aware. I know too much, what goes into these endeavors, and the intent behind them. I could do threads, get the clicks and likes, grow my Twitter following, re-use my old blog posts, write single-sentence LinkedIn posts with undertones of unnecessary oversharing and neuroticism, and leverage it to be part of other circles and communities.

But it would serve no purpose other than feeding my own vanity. Maintaining that status is exhausting. If you’re a startup founder trying to be known in a circle, sure, this is a smart tactic to generate attention. But to do it because everyone else is doing it just creates more noise and regurgitated ideas. It's not interesting. And you waste time on things that don't matter.

Like those goldmines I mentioned before, this observation has more to do with cycles in industries. Pre-internet was a cycle. The dot com crash was another. The beginning of social media was a cycle. Blogs. Podcasts. Influencers. Branded content (where did those disclaimers go?). Now we have crypto, web3, NFTs and, oh look, back to newsletters and podcasts.

Where did it go?

The concept of a town square makes me think of merchant or artisan guilds from Europe. 

A guild was an association of craftspeople that supported one another, e.g., carpentry, masonry, painting, and merchants of all kinds. There was mentorship, education, and economic and moral support. Sending a child to become an apprentice within a guild ensured they would have a job and be able to sustain themselves as they matured because they had a skill that was in demand. Guilds also set the standards of quality and values. They upheld principles and attitudes that would make the craft — and industry — better. They shared knowledge. They held each other accountable. It was, in every sense of the word, a community.

These kinds of guilds or communities are vital to people and the growth of their craft. People want to believe that they can evolve in the comfort and solitude of their studio or home, distant from other people. That is so wrong. We absorb from others; we are shaped by the ideas and conversations from our close circles. 

Reliability and Information

When I study the history of guilds — and inevitably their downfall — the two elemental things that stand out are relationships and information. Guilds thrived because it was the center of knowledge. It was about relationships because they had each other’s backs, even though they may have been in competition with each other. 

According to this research [emphasis mine]: “In the 16th century, the Atlantic coast was undergoing a disruptive commercial revolution with the discovery of new sea routes to Asia and the Americas. Cities at the Atlantic coast, including those in northwestern Europe, became attractive commercial hubs, with high population growth. The bustling Atlantic coast gave merchants the greatest incentive to form new connections with unfamiliar traders, and so to rely less on the existing guild system. My research shows that all the cities in which guild monopolies declined were close to the Atlantic coast. In addition, the cities that reformed their guilds (but did not dismantle them), as happened in northern Italy, were also close to the sea, if not on the Atlantic coast.”

On the other side of the same coin, the spread of information was also a major factor in the evolution of guilds and trade: 

“Long-distance trade necessitated doing business in regions and markets about which the merchants had limited information, and with partners or agents who could not be easily monitored. So, informational asymmetry and moral hazard made this impersonal long-distance trade difficult. . . . For impersonal exchange to emerge, search costs needed to be low, and traders needed to feel confident about the reliability of risky impersonal partnerships. Any improvements in the availability of information would help to increase this reliability.”

Guilds thrived because they dealt with smaller groups. It is easier to manage relationships, processes, and outputs. 

If reliability and information change how people behave, it makes sense why the internet was so compelling. Humans desire connection and the internet did a marvelous job of doing that at an infinite scale. Then we humans copy and pasted information onto this new digital world. And the gathering of information, and audiences willing to devour it, transformed how people gain information and build relationships/trust. 

Where’s your guild, your community?

If publications during the 2010s were essentially digital town squares or mini guilds for creatives like me, what happened to them?

It’s the unfortunate reality of all good things ending: They didn’t make money.

Many publications were acquired by larger companies because the companies saw the value of “owning” an audience and expanding their business with a media brand. Many failed because of the wrong business model, because of culture, because of the wrong leaders, because video took over. 

Also, independent owners of very successful blogs shut down or sold. Whether it was the business model being unsustainable or the very nature of being a publisher was exhausting — nearly everyone who was around when I started has shifted to new ventures or disappeared entirely. A gold rush indeed.

Because of blogs and social media, information was produced at an alarming rate. The nature of reliability changed, too. The number of followers, credentials in your bio, a verified checkmark, a well-designed website, strong copywriting, and even a good headshot all influence whether we give someone our attention or give them our money. Back during guild days, it probably had more to do with your family lineage, your products, and your reputation. 

It’s hard to pin the tipping point, but sometime around 2015-16, I think the cultural attitude of social media flipped on its head. Twitter was consumed by journalism/media circles and disinformation and outrage porn were far more engaging than reading a blog or attending a webinar.

And the average person got a lot smarter, understanding the fabric of social media, how it worked, and how powerful it really was. The hunger for fame grew ruthlessly. Community then became a buzzword for tasteless tech marketers and clueless executives to use in their landing pages and press releases. Everything became fucking content.

Aside from the fact that many media companies had outdated business models or had new leadership that wanted higher conversion from those publications — thus changing the game and the quality, and losing focus — there were other cultural moments that dissolved these creative town squares. 

  • “Once social-media platforms had trained users to spend more time performing and less time connecting, the stage was set for the major transformation, which began in 2009: the intensification of viral dynamics. . . . By 2013, social media had become a new game, with dynamics unlike those in 2008. If you were skillful or lucky, you might create a post that would ‘go viral’ and make you ‘internet famous’ for a few days. If you blundered, you could find yourself buried in hateful comments. Your posts rode to fame or ignominy based on the clicks of thousands of strangers, and you in turn contributed thousands of clicks to the game.” via Jonathan Haidt
  • 2015 was the peak bullshit era. The creative industry got very good at creating illusions of leadership. They sold empty promises of “workplace culture” only to sap the talent and labor of the naive. It continues today at scale.
  • The rise of the influencer showed that individuality, being very online, and having all the badges of follower count, selfies, or objects of envy could elicit fame, and if you had fame, you could get money and riches and a good life. Gen Z and millennials want to become famous. But they’re mostly miserable.
  • Pair all of this with the political landscape at the time, mistrust in government, politics, leadership, and our loss of locality. 
  • Personally, I think people just stopped reading. We started scrolling. Then video was highly engaging. The path to fame was alluring because it felt like it was one more piece of content away, whereas developing real mastery and skills was a game that requires patience and resilience, which is in short supply these days.

The nature of education was changing, too. My experience with the altMBA was a sign of what was to come and what people inherently are always searching for: connection.

These online cohort-based courses (CBCs) are everywhere, from Reforge to Maven to workshops or hackathons for engineers and programmers. These, in many ways, are representative of guilds. You can instantly find community in these places. Everyone is there to learn, to level up, so naturally there is an environment of support and knowledge sharing. It is easier to make new friends this way. You find like-minded people because enrolling into these programs requires serious dedication and vulnerability. And leveling up with others is the essence of a guild and the core behavior of a thriving community.

"The self is more of a superhighway for social influence than it is the impenetrable private fortress we believe it to be.” — Matthew D. Lieberman 

We need guilds. We need community. We need clubs and groups and small town squares where the size of the group is manageable. Because once we break Dunbar's law, cooperation and respect dissolve.

I think the internet is a powerful connector to begin these endeavors, but it isn’t where all interactions should live. Not anymore.


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