For the first time in nearly a decade, I started reading novels and poetry this year. It's showing me dimensions of writing that I missed during my non-fiction binge. It's where my curiosity lies, and it's beyond the edge of my ability. I want to pursue these sides of writing more intentionally, so I'm starting a new project soon that's shaped around these questions:
- How do you freeze your consciousness through words?
- How do you immerse readers in a scene?
- How do you collapse categories and explore your full range of interests?
- How do you experiment with sentence construction?
- How do you catch both the fish and the whale?
1. The Personal Dimension
This project is about sketching scenes through words, and then letting my mind explode into them, without restraint or apology. While I often hesitate to write myself into essays, this should give you a sense of knowing me that you wouldn't even get if you actually knew me.
Bringing my own life into my writing is something I usually approach with caution, if not avoiding it completely. When you're in the realm of non-fiction, it's easy to hide. I've dabbled a bit with writing fiction from the first person point of view in the Duke Surfs the Metaverse series. But in those essays, I'm cloaked as a psuedonym avatar, writing about hallucinogenic virtual worlds. Sure, it's vivid, it's three-dimensional, and it's a start, but it's still flat.
What I've been avoiding is using my own life experiences to express the human condition, through monologues, confessions, vulnerabilities, memories, failures, dreams, and embarrassments. There's an opportunity for any living person to freeze their consciousness into an artistic medium, and writing might be the most potent way to show somebody what it's like to occupy your own head.
The hesitation comes from a fear of the implications. What if you publish the thoughts you don't even share with friends, family, or your wife? What if you share with strangers the things you rarely admit to yourself? What if you get cancelled? What if you get crickets?
I'm inspired by recently reading the book "Dharma Bums," written by Jack Kerouac in 1958. It's based on his travels to San Francisco, where he stayed for few days before meeting up with others and venturing up into the mountains of northern California.
All the characters are pseudonyms based on people in his life :
- Ray Smith = Jack Keruoac
- Japhy Ryder = Gary Snyeder
- Alvah Goldbrook = Allen Ginsberg
Even though it's cloaked in fiction, the reader gets an unfiltered glimpse into what it's like being in the mind of Kerouac. He paints his surroundings, and you get to see his thoughts wander within a scene. It's beautiful, obscene, poetic, shocking, serene, visionary, insecure, confident and naive. It's contradictory and it shows the paradox of things. Without holding anything back, he gives you his life as an artifact. His life is his art.
Here I am, over fifty years after his death, reliving his forgotten memories in lucid detail, getting a portrait of this strange facet of the Beat counter-culture in 1958.
There's a weird sense of de ja vu. This book was written long before the Internet Age, but it's strikingly modern. There's a striving for similar things, pointing to the fact that human nature is static and unchanging. While we see this terrifying arc of progress unfolding in our life, these old novels point to the possibility that history rhymes and we're stuck in a loop.
He also expresses the opposite, "Jamais vu," the ideas you've never even conceived of - ideas that are unfamiliar, alien, and singular - generated by a mind you'll never meet - but nonetheless - can have a huge imprint on your psyche.
My mother's father, George, was a mechanical engineer who wanted to be a writer. He died a few years before I was born, so I never got to meet him. But I've seen his pictures, I've flicked through some books in his library, and I even read through three chapters of his alternate history World War 2 novel, written into a word processor on a computer in the 1980s.
It was fascinating to read the creative output from a descendent, but it didn't give me the sensation of knowing him. He wasn't one of the main characters.
The thought of freezing your life, culture, and philosophy into words, preserving them forever into the future, is, in my mind, a big motivator on why to write in the first place, and perhaps one of the most worthwhile things to do, especially when confronted with mortality.
When you write from the perspective of death and legacy, it loosens your hesitance over publishing on a stage where the average memory span is 24 hours. This project is about building the confidence to let my consciousness explode, without apology or restraint, into the center of a scene, through the medium of words.
It should give you a sense of knowing me that you wouldn't even get if you actually knew me.
My intended audience for this piece is my great grandchildren from the next century. I'm sure they'll be curious what life was like pre-simulation. Maybe they'll be shocked to witness a version of themselves existing and reflecting in 2021, a time that feels like ancient history. They're so far from existing that there's no reason to censor myself.
2. Scenes from California
I'll use "placemaking" to render a detailed version of my 10-day vacation in California. The first half takes place in San Francisco right as it's re-opening from the pandemic, and the second half is a road trip up to Mount Shasta (almost near Oregon) for a meditation treat, in a New-Age mountain town.
Something I enjoy, but never find a chance to do, is "immersive" writing. It's about painting the details of your surroundings - the architecture, the nature, the people and the weather and the sounds, or the suspiciously tall man with blue face paint who's wiping sweat off his third eye with a Starbucks napkin. It's about injecting detail so the reader can render something in their mind's eye.
Kerouac had a practice he called "sketching." It was about slowly and carefully observing your environment, like a painter gazing at the pigments of tree, to soak in and reflect on the details. The goal was to have these images reverberate around your memories to summon metaphors and associations.
It's a lot of fun to create a real-time chain between your perception, your subconscious, and your capacity to form language. But when you're writing non-fiction, you rarely get the chance to engage with a 3D environment.
I figured that my latest vacation from late June would be the perfect opportunity to practice this. I've been mostly stuck inside for 18 months. This was my first time flying since the pandemic. I spent more time in San Francisco this year than I have in nearby Manhattan. The trip ended with four days out in nature with no service. It was a sensory overload.
On top of that, it was also a pivotal point in my life. I left a career of 13 years in architecture, specializing in virtual reality visualization, to pursue a new phase: writing, and teaching it online. It was a quick transition. With society restarting, and a new adventure ahead, it was my first chance to reflect on where I was heading.
I didn't write much on the trip itself, but I "sketched" the entire thing. I have over 1,500 data points from 10 days, in the form of notes, sketches, voice recordings, and photos. While my past vacations are fuzzy, this is the highest-resolution thing I've ever captured. I recorded what I did, what I saw, the people I met, what was going through my head, the memories that surfaced, the content of my meditations, my dreams, and my reflections on the state of the world.
The macro structure of this project is done. Thank God. Scope on big projects can be like shifting tectonic plates, making it impossible to build on. There's a basic linear plot that reflects the way events actually unfolded.
The plot at it's core is similar to Dharma Bums, just a half-century later. The first half takes places in the city, and the second half in nature. The act of "placemaking" will ground the reader in each essay. Descriptions of scenes will ground and orient the reader through a winding stream of consciousness.
Here's a loose outline of how it all unfolds:
- JFK International Airport
- An abandoned Kearney Street
- Vesuvio, overflowing into Jack Kerouac Alley
- Mission Bay Resort with Internet friends
- The James Turrell structure in Golden Gate Park
- The AI Exhibit at the de Young Museum
- Fisherman's Wharf
- The North Face store
- The hotel room on Sutter Street
- Dolores Park
- The center of the Financial District
- WeWork Montgomery
- City Lights bookstore
- The walk to the Ferry Building
- Breakfast in Berkeley
- I-5 road trip from the back seat
- The crystal shop in town
- Arriving at Stewart Mineral Strings
- Trance states on an Indian Bridge
- Yoga on a deck at 6 am
- Ascension Rock
- Swimming at Castle Lake
- The cedar dining hall
- The base of Mt. Shasta
- The hike up Mt. Shasta
- The Labyrinth
- Vision quest at Panther Meadows
- The winding walk down
- Lake Siskiyou at midnight
- The day the fire started
3. The Collapse of Categories
Weaving in and out of each scene will be a non-linear stream of memories, dialogues, histories, theories, rambles, prophecies, day dreams, twisted fantasies, and productivity advice.
When we're writing non-fiction essays for the Internet, the common approach is to have a single theme per essay. Our whole body of work can be divided into a series of silos. On my site, you'll find essays on either virtual reality, simulation fiction, writing, Notion, psychology, or digital networks.
My goal is to melt the boundaries between categories, and have all my curiosities fuse into a single thing. The sequence of events is the "generator," meaning that any object in a scene can act as a portal to tap into an associated series of thoughts, which could span topics and genres. Over time, as the reader moves from portal to portal, a diverse range of ideas will pop up.
The approach of fusing a linear path with non-linear thoughts is inspired by the book "Mrs. Dalloway," by Virginia Woolf. There's a simple premise that underlies the whole thing: "Mrs. Dalloway is going to get flowers for a party she's throwing that night." The book is a single chapter (at 194 pages). As she moves through town, a minute detail she observes might blossom into a multi-page stream of thought, covering the love of London life in 1925, the shell-shock suicides after World War 1, and just about everything in between.
There are a list of themes that will emerge throughout the project.
- The memories, thoughts, and relationships of "Dean Dukelis" (Michael Dean's alter ego)
- Architectural descriptions of airport, cities, roads, museums, and nature
- The craft of writing, inspirations, cohort-based courses, and the Creator Economy
- Capitalism, advertising, and optimization culture
- The Strauss-Howe generational theory & loops
- The Beat Generation & counter-cultures
- Emerging technology: virtual reality, artificial intelligence, cryptocurrency
- Esoteric: meditations, dreams, psychedelics, consciousness, extra-terrestrial life
Ultimately, this thing will exist somewhere at the intersection of auto-biography, fiction, and non-fiction. It's an attempt at synthesis. While my website is a mosaic, with each idea acting as a self-contained brick, this one will be more like a psychedelic mess, hopefully held together by a sequence of places. The end result should be messy, hopefully funny, and more importantly, it should be an honest capture of the depths of my mind.
4. Prose Poetry
"Experiment with all manner of poetics, erotic broken grammars, ecstatic religions, heathen outpourings speaking in tongues, bombast public speech, automatic scribblings, surrealistic sensings, streams of consciousness, found sounds, rants and raves - to create your own limbic, your own underlying voice, your ur voice." - Lawrence Ferlinghetti
I'm fascinated by a writing style called "prose poetry." It stripes away the line breaks of poetry, but then injects imagery, metaphor, and sound into prose, stretching the nature of what a sentence can be. When you read the Beats, you can jump to any page, and just marvel at a single sentence. I found myself stuffing tiny prose-poetry books into my jacket pockets when I was in San Francisco.
While the Writing Studio lets me focus on analysis, form, and structure - this project is exciting for me because it lets me explore the poetic side of the craft. The pillars of structure (hierarchy, parallelism, logic, and compression) are suspended, sometimes acted upon subconsciously, so that the conscious mind can focus on the sound and imagery within sentences.
I find myself editing these essays, and even stretching the way I form sentences, based on the way they sound when they're read aloud. It's a bit of a lost art, but a lot writing from the Beat Generation was written with the intention of being read. Hunter S. Thompson did this too.
It's a well cited meme that Thompson re-wrote novels like "The Great Gatsby" so he knew what it felt like to read a great novel. What's left out is that he would read these novels out loud as he typed them. Phonetics were a high priority for him, and it even carried into his editing process. He'd invite his friends over for drinks and drugs, have them read his drafts out loud, give a "thank you," and then rush away to revise the piece, with no additional comments.
An exciting part of this project is that I don't know exactly how it's all going to unfold. There is a known linear plot based on what happened IRL, but there are infinite ways for the details to unfold. If X event happened, and it triggered a memory of Y, there are so many possible associations that can come up when I render Y onto the page.
Kerouac talks about avoiding pre-conceived ideas when unfolding an image. His approach is to spawn language from the "jewel center of interest" in the subject, at the moment of writing. Basically, it's an art of free-associating and following the paths with the highest resonance. He describes his sketches as "undisturbed flows" into mind, to extract "secret idea-words" that derive from personal experience.
In the act of unfolding an image, it can lead to massive run-on sentences, sometimes the length of entire atomic essays. The stability of a sentence is secondary to a flood of details that paint a lucid sense of place. These can be really powerful, especially when they resolve in counter-intuitive ways, or if they're nested in between short sentences.
5 - The Beat Generation on Twitter
While the macro-structure is based on real-life events, the story will unfold and be shared one scene at a time.
This is an ambitious project, and I'm really against the idea of diving into one project, in isolation, at the expense of everything else happening in my life. It's a huge risk.
The way Dharma Bums was written is the epitome of a heavy lift. Kerouac wrote the whole thing in 11 days, averaging 18 hours of writing a day, fueled by coffee, alcohol, and amphetamines, at his mother's house in Orlando, through a rented typewriter and a scroll suspended from the ceiling.
I've always equated ambitious projects to hunting whales. There's a quote from Lawrence Ferlinghetti that stands out to me:
"Pursue the White Whale but don’t harpoon it. Catch its song instead.”
Instead of literally catching the whale, there must be a way to catch a series of fish, that when strung together, approximate the majestic qualities of the whale which can never be caught or conveyed.
Almost a year ago, the night that Write of Passage 5 ended, I remember pondering with Ritesh Reddy, the king of Play, around how the Beat Generation, the original pranksters, would utilize social media. "How would Jack Kerouac have used Twitter?"
My plan is to post one scene every day. While there is an order of events, and I have a loose idea of what comes next, I don't know exactly how it will unfold. After writing a few of these essays, I learned not to cling to a pre-set division of scenes. I thought my airport experience and flight to San Francisco would be a single essay, but now it's shaping up to be over 10 individual essays, each at around 400 words.
There's no time limit to complete this project. It will take however many days it needs. Working from a loose chronological outline, whatever I can finish within a given day will be packaged into an atomic essay and shared on Twitter.
While I've publishing over 50 essays in the first half of 2021, I haven't been proactive on Twitter. This project is a way for me to share something daily through a quantity-driven social network. I'm basically writing a book, and releasing one scene at a time in public, almost like a pre-Netflix TV show.
I originally conceived this project as my approach to Ship-30-for-30, an online writing course about daily publishing. I was in Mount Shasta without service when it launched, so I never really got on the bandwagon.
Underlying Ship 30 is the idea around discovering your niche through feedback and metrics. My approach is unorthodox given the ethos of the course, but I believe that being both prolific and original can open up a third door, unique to you, that can't be discovered through optimizing the paths that others have discovered.