The Underground Blogosphere

On espresso houses, outlaw intellectuals, and the possibility of a new independent web

I have a romantic weakness for the cultural outlaws of the 1960s.

Not necessarily the famous ones, although I’ve always had a soft spot for the Beats, the wandering poets, the jazz musicians, the folk singers who could turn three chords and a borrowed guitar into a minor political disturbance. I’m thinking more about the nameless regulars who populated the espresso houses and taverns of Greenwich Village, North Beach, and Berkeley. The freelance intellectuals, self-styled philosophers, dissenters, artists, anarchists, mystics, and assorted cultural misfits who seemed to have appointed themselves custodians of a different kind of life.

I picture them gathered around small wooden tables, drinking coffee that has long gone cold, arguing about existentialism, politics, poetry, and whether civilisation took a wrong turn somewhere around the invention of the assembly line. Cigarette smoke curls beneath the ceiling. A jazz quartet is working its way through something improvisational in the basement downstairs. Someone has brought a manuscript. Someone else has brought a bottle. A third person has brought an argument that will probably outlast both.

Scattered across the tables are copies of the Los Angeles Free Press, the Berkeley Barb (https://www.berkeleypubliclibrary., and the East Village Other. Newspapers that looked as though someone had liberated a printing press and decided to see how much trouble they could cause before breakfast.

I know I’m romanticising it.

The actual rooms were probably uncomfortable, the coffee frequently terrible, and a good many of the conversations less profound than my imagination allows. Bohemian life had its own hierarchies, hypocrisies, and exclusions. Some of the men who spoke most eloquently about liberation were considerably less enthusiastic when women began demanding a share of it.

But hey, romance has its uses.

Sometimes an imagined past does something more interesting than preserve history. It illuminates a possibility we’ve forgotten how to imagine in the present.

What attracts me to that world isn’t really the smoke, the jazz, or the battered notebooks, although I’ll happily take the jazz and notebooks. It’s the sheer audacity of people who decided they didn’t need institutional permission to become intellectuals, writers, or artists.

They simply started living that way.

They arranged their days around ideas, conversation, artistic experimentation, and cultural dissent. They published little magazines nobody had commissioned. They organised poetry readings in rooms that weren’t designed for poetry. They started newspapers because the existing newspapers weren’t saying what needed to be said, or weren’t saying it in a language they recognised.

They made their own intellectual neighbourhoods. And perhaps most importantly, they didn’t wait for the world to recognise them before they got on with living.

I find that thought increasingly compelling.

The little newspapers that refused to behave

The underground press of the 1960s fascinates me because those publications were doing something more interesting than reporting the news.

They were helping to invent a culture.

When Art Kunkin launched the Los Angeles Free Press in 1964, he wasn’t simply introducing another editorial perspective into the existing marketplace of ideas. He was opening another door into public conversation. A door through which could pass stories, arguments, artwork, and provocations that the established press either ignored or preferred not to acknowledge.

The Berkeley Barb arrived the following year, carrying the peculiar energies of a city becoming a laboratory for political dissent. The East Village Other mixed politics with psychedelia, comics, poetry, mysticism, and the general conviction that the newspaper itself ought to be treated as a medium for experimentation.

Their pages could be brilliant, infuriating, outrageous, insightful, occasionally ridiculous.
Sometimes all at once.

I like that.

Not the irresponsibility that sometimes accompanied it, nor the blind spots that were often as revealing as the articles themselves. What interests me is the willingness to let the publication acquire a personality. To allow the messy, contradictory, unpredictable nature of human thought to show through the machinery of production.

You could pick up one of these papers and sense that a particular collection of human beings had assembled it. That there were arguments behind the pages. Obsessions. Personalities. Unresolved philosophical disputes. Somebody’s beautiful but possibly unhinged theory about how the world ought to work.

The newspaper was not merely a container for information.

It was an expression of a community thinking aloud.

And when the Underground Press Syndicate began connecting these publications, allowing them to exchange stories and material across cities, something remarkable happened. A loose network of independent editorial experiments developed its own cultural circulation system.

Ideas moved from one city to another without having to pass through a central editorial authority. A decentralised commons made from paper, ink, cheap printing presses, stubbornness, and a shared appetite for dissent. The more I think about it, the more familiar the arrangement becomes. Because several decades later, another generation of cultural misfits discovered a medium through which they could do something remarkably similar.

Only this time, they didn’t need a printing press.

When the coffeehouse went digital

I remember the early internet as a place where you could lose yourself.

Not in the contemporary sense of disappearing into an endless stream of algorithmically curated distractions, but in the older, more adventurous sense of wandering.

You followed a hyperlink because something about the words intrigued you. You arrived on somebody’s homepage, discovered a collection of essays, followed their blogroll to another writer, and somehow found yourself three hours later reading the reflections of a complete stranger living halfway around the world.

There was no particular destination.

That was part of the pleasure.

The websites didn’t all look alike. Some were beautiful. Some were hideous. Many were endearingly amateurish. People experimented with backgrounds, fonts, animated images, peculiar navigation systems, and arrangements of words and pictures that would give a contemporary user-experience designer a nervous breakdown.

I remember visiting sites that seemed to have been assembled by someone who had discovered every available feature of HTML and felt morally obliged to use them all.

Glorious.

The web felt like a place under construction, and everyone seemed to be building something different.

Not optimised landing pages. Not carefully engineered conversion funnels.

Places.

Little territories of personality.

Some were barely more than a page of links. Others had sprawling archives of essays, photographs, poems, manifestos, reading notes, and observations about ordinary life. You could spend an evening exploring somebody’s website and gradually acquire a sense of their intellectual temperament.

What interested them. What irritated them. Which writers they admired. Where their curiosity tended to wander when nobody was directing it.

And then there were the conversations.

I used to spend hours in IRC chatrooms talking to people who shared my interests. We’d begin somewhere ordinary enough, perhaps with a question about a book, a piece of music, or an idea somebody had encountered during the day. Then the conversation would wander.

Philosophy would become religion. Religion would become consciousness. Consciousness would become artificial intelligence, science fiction, politics, or the possibility that reality wasn’t quite what we imagined it to be.

Someone would introduce a new thought.

Someone else would disagree.

A third person would post a link.

And off we’d go again.

Sometimes the conversations were so absorbing that I simply didn’t go to bed.
I’d glance at the clock, realise it was two in the morning, decide to stay another half-hour, and look up again to discover that the sun was coming up.

The night had disappeared into conversation.

I wasn’t producing content. I wasn’t developing a personal brand. I wasn’t networking with strategic intention or cultivating an audience for some future commercial venture.

I was talking to people.

And for those few hours, those people, scattered across the planet, were my intellectual neighbourhood.

It’s difficult to explain the excitement of that discovery to someone who has grown up with constant connectivity. Today we take it for granted that we can communicate with almost anyone, anywhere. But there was a time when encountering someone on another continent who shared your obscure intellectual enthusiasms felt almost miraculous.

The world had suddenly become populated by people you hadn’t known existed.

People willing to follow a conversation wherever it led.

People who didn’t think it particularly strange to spend half the night arguing about an idea that had no obvious practical application.

This was the espresso house without walls.

The neighbourhood had become planetary.

And the emerging blogosphere gave that culture another dimension.

A blog post could be the beginning of a conversation rather than its conclusion. Someone would respond in the comments. Another blogger would pick up the argument on their own site. A third would take one sentence, turn it sideways, and discover an entirely different question hiding inside it.

Trackbacks, blogrolls, hyperlinks, comment threads, forums, IRC channels.

A sprawling, untidy ecology of conversation.

The blog was the café.

The comments were the regulars around the table.

The hyperlinks were the streets connecting one neighbourhood to another.

And the blogger wasn’t necessarily performing for an audience.

They were keeping company.

The slow enclosure of the open web

Somewhere along the way, the neighbourhood began changing.

The transformation wasn’t sudden. Nobody announced that the era of the independent web had ended and everyone was now required to move into a corporate platform.

We migrated willingly.

And there were good reasons.

Facebook made it easier to find people. Twitter made it easier to participate in public conversation. Instagram made visual sharing effortless. The technical barriers that had once made personal publishing a mildly eccentric pursuit were disappearing.

Why maintain a blog, wrestle with templates, moderate comments, and spend hours tinkering with a website when you could post a thought and immediately receive responses?

The crowds were gathering elsewhere.

And naturally, we followed.

I did too.

For a while, social media seemed like an amplification of everything that had made the early web exciting. More people, more conversations, more opportunities for unexpected encounters.

But the architecture of these places began quietly altering the nature of our participation.

We stopped visiting websites and began inhabiting feeds.

We stopped following hyperlinks into unknown intellectual territory and increasingly accepted whatever appeared next in the stream.

Our online selves became standardised profiles, housed inside environments whose owners could rearrange the furniture, move the doors, or change the rules whenever they wished.

The old web had felt like a rambling city filled with strange independent establishments.

The platform web increasingly resembled an enormous shopping mall.

Convenient, brightly lit, carefully designed to keep you inside.

And perhaps the most consequential change was linguistic.

Followers. Reach. Engagement. Impressions. Growth. Conversion.

We began measuring relationships in the vocabulary of marketing.

Writing became content.

Conversation became engagement.

Readers became an audience to be acquired, retained, and monetised.

Of course, none of these tendencies began with social media. Newspapers needed circulation figures. Artists needed patrons.
Underground publications needed advertisers, however much their editors despised commercial society.

And genuine friendships, intellectual communities, and extraordinary conversations continue to exist on the platforms. I’ve found plenty of them myself.

But something in the underlying orientation changed.

The web was becoming less a collection of places we visited and more a collection of systems competing to occupy our attention.

The medium had begun reshaping the message.

I sometimes wonder whether the most significant loss was not ownership of our content, or even control over its distribution.

It was the loss of the habit of wandering.

The willingness to follow an idea without knowing where it would lead.

To read something because it was interesting, not because it had been recommended to us by a machine trained to predict our behaviour.

To linger in an obscure corner of the web simply because we liked the company.

A room of one’s own, rented from somebody else

Lately, I’ve been watching another migration.

A number of bloggers I’ve followed for years have abandoned their independent websites, or allowed them to fall quiet, and moved their publishing activities to Substack.

I understand the attraction.

Substack has recognised something that the large social platforms have often neglected. People still want sustained relationships with writers and thinkers. They want more than a succession of disposable updates. They want essays, newsletters, podcasts, conversations, and the opportunity to support work that matters to them.

And Substack has assembled these activities into an impressively convenient environment.

A newsletter, a blog, a podcast, video, livestreaming, subscriber chat, short-form social updates, paid subscriptions. Much of what once required a small constellation of services can now be managed from one place.

I tried it myself for a while.

And I can see why people stay.

But something about the arrangement never quite sat comfortably with me.

Part of it was the atmosphere. Part of it was the feeling that I’d moved from one form of enclosure into another, admittedly more comfortable, more literary, and considerably better furnished.

Mostly, though, I missed the freedom to make something strange.

I wanted to experiment with the design of the page. To scatter fragments across an unconventional layout. To build interactive elements, unusual navigation systems, visual essays, and digital objects that refused to behave like conventional articles.

I wanted to treat the website itself as part of the creative work.

Substack allows considerable freedom over what a writer says, and it provides ways to export content and subscriber lists. These are meaningful advantages. But its publishing environment remains largely standardised.

And I found myself thinking about the difference between having the freedom to publish and having the freedom to determine what publishing might be.

It sounds like a small distinction.

It isn’t.

The architecture of a space influences what can happen there.

A lecture theatre encourages a different kind of encounter from a café. A shopping mall invites different behaviours from a public square. A newspaper column shapes thought differently from a notebook, and a notebook differently from a garden of interconnected ideas.

The form is never entirely separate from the thinking.

I want the freedom to experiment with both.

I want to write an essay one day and construct an interactive philosophical toy the next. I want to be able to follow a metaphor into a completely different medium without discovering that the architecture of my publishing platform has already decided which kinds of expression are permissible.

Not because every experiment will succeed.

Most probably won’t.

But because the freedom to attempt something peculiar is part of what makes independent publishing interesting in the first place.

Sometimes the strange little side project is where the genuinely new thought first appears.

Rumours from the underground

I’ve been wondering lately whether the conditions might be ripening for an underground renaissance of the blogosphere.

Not a nostalgic restoration of the early 2000s. I’m not proposing that we rebuild the web exactly as it existed when everyone was experimenting with animated GIFs and arguing about whether Blogger or Movable Type was the superior expression of human freedom.

Although I confess a certain affection for those arguments.

I’m imagining something less archaeological.

A renewal of the idea that the web can be a place for independent cultural life rather than merely a distribution network for material destined to circulate through corporate platforms.

There are signs of dissatisfaction with the existing arrangements.

People have grown weary of doomscrolling, the monetisation of attention, the relentless pressure to produce and perform, the sense that every digital interaction is being measured, classified, and fed back into a system designed to extract something from it.

Some have retreated into private groups, messaging channels, online communities, and membership spaces. Others have migrated toward newsletters, hoping to recover a more direct relationship between writers and readers.

And yet even these refuges have a peculiar tendency to acquire the language and machinery of commerce.

An interesting gathering place becomes a community-building opportunity. A community becomes a membership proposition. The membership proposition acquires tiers, funnels, launch strategies, and an enthusiastic individual explaining how everyone can turn their authentic selves into recurring revenue.

Sometimes it seems impossible to enter a digital room without somebody eventually appearing with a clipboard.

Meanwhile, the independent web has been quietly carrying on.

People still maintain personal websites. The IndieWeb continues to develop ways for people to publish from spaces they control. RSS still works, despite having been declared obsolete approximately every six months for the past twenty years. Webmentions allow conversations to move between independent websites. Blogrolls, those wonderfully informal maps of intellectual affinity, continue to connect one curious mind to another.

And a new generation is discovering that a personal website can be more than a professional portfolio or a digital business card.

It can be a small, handmade corner of the internet.

A place to think in public.

A place to collect fragments, experiment with ideas, share discoveries, and invite conversation.

None of this guarantees a renaissance.

Dissatisfaction with the dominant platforms doesn’t automatically produce an appetite for independent publishing. Some people will simply retreat further into private conversations. Others will decide that the effort of maintaining a website isn’t worth the trouble.

And there are practical difficulties. Discovery remains hard. Moderation takes effort. Independent publishing asks more of its participants than clicking a button inside a platform that has already solved most of the technical problems.

But perhaps we’ve been asking the wrong question.

Perhaps the future of independent blogging doesn’t depend on persuading millions of people to abandon social media.

Perhaps it depends on enough people deciding that they want to inhabit the web differently.

Not necessarily more efficiently.

Not necessarily more profitably.

Differently.

And making places where that difference can flourish.

The outlaw intellectual returns

I keep returning to the figure of the freelance intellectual.

The person who moves between disciplines without worrying too much about professional boundaries. Who reads philosophy in the morning, listens to jazz in the afternoon, wanders through the city collecting impressions, and spends the evening arguing with friends about some question that has lodged itself in the imagination.

The wandering essayist.

The amateur in the older sense of the word: someone motivated by love of the activity itself.

Paul Goodman comes to mind.
So does Diane di Prima moving between poetry, politics, publishing, and spiritual exploration. Or Ed Sanders, whose life seemed to disregard the conventional partitions separating literature, music, political activism, and cultural mischief.

These people weren’t interchangeable, and their differences mattered. But there was a kind of intellectual mobility among them that I find enormously attractive.

The freedom to move laterally.

To pursue a question because it has seized your imagination, not because it belongs within the boundaries of your professional specialism.

To regard thinking as an adventure rather than a qualification.

And I wonder what this figure might become in the age of artificial intelligence.

There’s an interesting tension here.

Much of the public conversation about AI has been organised around productivity. How can we write faster, produce more, automate our workflows, scale our businesses, and accomplish in an afternoon what previously required a week?

Perfectly reasonable questions.

But they don’t particularly excite me.

What excites me is the possibility that these technologies might enlarge the imaginative territory available to the individual.

A writer who can build software.

An artist who can create interactive philosophical environments.

A curious amateur who can experiment with ideas that previously required access to specialised institutions or technical expertise.

A blogger who can move between prose, audio, moving images, code, and forms of expression we haven’t quite named yet.

I find myself thinking about Ivan Illich’s Tools for Conviviality, and his concern with tools that enlarge people’s capacity to act autonomously rather than making them dependent on increasingly elaborate systems of professional and institutional control.

What would a convivial web look like now?

Not necessarily a technologically primitive one.

Perhaps quite the opposite.

Perhaps the next underground will be technologically adventurous, using the very tools developed by enormous corporations to create little pockets of cultural independence.

There is a paradox in that, certainly. Sovereignty built on rented infrastructure is never absolute. The same technologies that enable independent experimentation can also deepen dependency, concentrate power, and flood the web with material nobody particularly wanted to read.

But perhaps independence has never meant complete separation from the systems around us.

Those underground newspapers depended on printing equipment, paper suppliers, distribution networks, advertisers, and sometimes the generosity of people with money. Their independence existed in the choices they made within those entanglements. And perhaps that’s where ours must exist too.

Not in the fantasy of technological purity.

In the determination to remain intellectually sovereign.

To use the tools without allowing the tools to determine the purposes.

To resist the demand that every creative activity justify itself in terms of efficiency, growth, or commercial return.

To reserve some portion of life for experiments whose value cannot be predicted in advance.

And, perhaps most radically, to remain small when smallness suits the work.

A jazz musician playing to thirty people in a basement doesn’t need to fill an arena for the music to matter.

A little magazine circulating among a few hundred readers can still alter the intellectual atmosphere of a community.

A blog doesn’t have to become a media company.

Sometimes it only needs to remain a place where interesting things happen.

The company of curious minds

Somewhere in the evolution of online publishing, we began confusing an audience with a community.

I think about this whenever I remember those late nights on IRC.

Nobody was building a following.

Nobody was calculating the optimal frequency of contributions to maximise engagement.

There were simply people in a room, or rather people scattered around the world who had somehow managed to create the feeling of being in a room together.

And that difference matters.
An audience gathers around something you produce.

Company gathers around something you share.

An audience can be measured in numbers. Company is experienced in the quality of the encounter.

Of course, these aren’t mutually exclusive categories. Readers become friends. Audiences develop into communities. Writers can earn a living without transforming every relationship into a commercial transaction.

But the distinction reveals something about the posture we adopt toward the people who encounter our work.

Am I publishing to acquire attention?

Or am I putting something into the world because I want to see what might happen when it encounters another mind?

The first question leads quite naturally toward metrics, strategies, schedules, and growth.

The second leads toward conversation.

And conversation is a peculiar thing.

You can’t entirely control it. You can begin with a question, an argument, a story, or a half-formed suspicion about the nature of reality, but once another person responds, the thought is no longer exclusively yours.

Something enters the space between you.

An unexpected association.

A disagreement that opens another path.

A sentence that changes the direction of the whole inquiry.

Perhaps this is why I remain so attached to the hyperlink.

A hyperlink is a small act of generosity, or mischief, depending on where it leads.

It says: Here is something I encountered. I wonder what you’ll make of it.

It opens a door without insisting that anyone walk through.

And if they do, there’s no guarantee they’ll return by the same route.

That seems to me a far more interesting conception of intellectual life than the endless accumulation of followers.

Not a hierarchy of creators and consumers.

A web of encounters.

A constellation of curious minds, each pursuing their own questions, occasionally crossing paths, exchanging fragments, and then wandering off again.

Some conversations might last five minutes.

Others might stretch until sunrise.

Keeping the lights on

I don’t know whether the blogosphere is on the verge of an underground renaissance.

Perhaps I’m allowing my affection for the espresso houses and outlaw intellectuals to colour my assessment of the present. Perhaps there will never again be anything resembling the early blogosphere, just as the Greenwich Village of the Beats could never quite be recreated once it became an object of cultural nostalgia.

Every underground becomes something else when enough people discover it.

The neighbourhood changes.

The rents go up.

The tourists arrive.

Someone opens a themed coffee shop.

And eventually somebody starts selling T-shirts commemorating the rebellion.

Still, I don’t think the possibility has disappeared.

Because the thing that made those places interesting wasn’t fundamentally the architecture, the technology, or even the historical moment.

It was the willingness of people to organise some part of their lives around curiosity, intellectual freedom, experimentation, and one another.

That possibility doesn’t belong to the 1960s.

It doesn’t belong to the early internet either.

And it doesn’t require a manifesto, a movement, or another entrepreneurial visionary promising to reinvent community through a revolutionary new platform.

Perhaps all it requires is that we keep making places.

Keep writing.

Keep following the strange links.

Keep leaving the door open for whoever happens to wander past.

I return, finally, to the espresso house.

Only now the table might be in a kitchen in Warwickshire, a small apartment in Tokyo, or a study overlooking a street in Berlin.

The newspapers have become independent websites.

The jazz is playing somewhere in the background.

And the people gathered around the table are scattered across time zones, connected by the peculiar miracle of a network that allows strangers to discover they share an enthusiasm for the same obscure questions.

It’s getting late.

The coffee has gone cold.
Someone introduces a new idea into the conversation, something none of us had considered before, and suddenly everybody is talking again.

Nobody seems particularly concerned about the time.

Outside, the night is giving way to morning.

And somewhere, in another corner of the web, a light is still burning.

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