These live sessions are treasure troves of wisdom and ideas, and we invite our Premium+ members to pull up a chair. Each recording also gets added to a private YouTube playlist (link behind the paywall below) for our members to rewatch any time.

Here’s a preview of some session’s we’ve hosted:

• In December, we hosted Allegra Preuss for an online yoga class to get into our bodies and out of our minds. Pure bliss.
  
  

• In January, we hosted for a session on How to write an uningnorable email. Carly might be the best cold email writer on the internet. More than one person messaged us after the session saying the examples she shared brought them to tears.
  
  

• In February, we hosted Lucas Crespo (the creative director at Every) for a session on how to build a brand identity using your taste + AI. This was one of the most mind opening hours of our year so far.
  
  

• In March, we hosted Emmett Shine, the wildly creative mind behind brands like Warby Parker, Sweetgreen, and Hims & Hers for a whatever you call the opposite of performative session. He jumped between Figma and a dozen tools, and gave us a raw window into his creative process. He described the future of work with a Pez dispenser analogy and shared his template for brand guidelines to share with agents. Insanely valuable stuff.
  

In April, we’re hosting , one of our favorite contemporary thinkers for a session on How to pull the human out of the machine. Luke is the Director of the Cluny Institute, a home for people at the intersection of Athens (arts and philosophy), Jerusalem (faith and religion), and Silicon Valley (tech and venture). Which is to say, he’s one of the few people approaching this moment with spiritual seriousness and moral imagination.

You can RSVP here, and because we really want you to get a taste of this one, you can use code PREMIUMPASS for free access ;)

P.S. If you didn’t read in between the lines, this is us continuing our patient campaign to lure you away from the great-but-ultimately-lacking-free-tier and make the case, without shame, that for $100/year Sublime is the most underpriced membership on Earth.

The recordings + assets for all past sessions are below the paywall. If you’re a Premium+ member and have trouble accessing, email us at sari@sublime.app.

Alsooo, let us know in the comments who’d you like us to host a session with and we’ll do our best to make it happen.

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Last week, Kyle Chayka published a piece in the New Yorker titled why tech bros are now obsessed with taste.

Sublime makes a brief appearance, described as: ”a bookmarking app th…

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This is the story of how those sounds made their way into Sublime.

But really, it’s about people, the things we choose to care about, and how ideas move through us.

With the next version of Sublime on the way + these sounds returning with it, it felt like a good moment to (re)tell it.

Enjoy ;)

This mechanical calculator was supposed to be a gift for Hitler. 

And that’s the least interesting thing about it.

The sounds that the calculator makes – crisp, decisive, mechanical sounds – we recorded them and used them as clicks on our website. You can hear them below:

What’s all this have to do with Sublime?
Nothing. And also everything.

1930s

It’s hard to say when the story starts.

But let’s say it begins here, with an Austrian engineer named Curt Herzstark.

Calculators at this point are huge, like the size of a cash register huge. All anyone wants is a pocket-sized tiny calculator, but no one knows how to make one. Less than 100 years ago and no one in the entire world has a calculator that fits into their pocket. 

So Curt decides that rather than looking forward in time for a solution, he’ll imagine himself into a future where the calculator’s already invented, and he’ll look backwards:

I thought to myself, I'll pretend that I have already invented everything. What does this kind of machine really have to look like, so that someone could use it?

By 1938 he has a patent. 

Then WWII begins.

Curt is sent to a concentration camp. The SS officers find out he’s got plans for a revolutionary calculator and tell him to finish making it, that it’ll be a gift for Hitler once the Germans win the war.

Hitler never got the calculator.

1949

The Curta goes on sale for $125 USD ($1,647 today).

It’s a hit with engineers, traveling accountants, pilots, even rally drivers. For twenty years the Curta sells – 150k units in total – and then everything stops.

Simpler, cheaper, easier to reproduce, the electric calculator takes over.

And just like that, the Curta was dead.

Until it wasn’t.

2022

The Curta becomes a collector’s item and now sells on eBay for $1-2k. 

That’s how the artist Shl0ms buys one. He tweets about the whole story.

Which is how a man named Gabriel Nessim Schloser in Madrid, España sees that tweet.

Gabriel, who is building Sublime, is moved. Gabriel’s great-grandparents survived the holocaust, and he thought Curt delayed the design on purpose until the war ended to save his life.

Maybe Curt did.

Gabriel goes on eBay to get one, but they’re all too expensive.

Except for one.

Owned by a guy from Turkey who’d just come into the possession of things gifted to him by his old lady neighbor, recently deceased.

Including a Curta calculator.

The guy wants 800€ for it.

Gabriel and the dude get on the phone and haggle for 45 min. Sending each other photos of IDs to prove they're good for it. But they couldn’t know for sure.

So Gabriel ends up wiring 600€.
And he waits.
And waits.
And the Curta arrives.

2023

Gabriel is working on Sublime's first website.
Designing it.
Making sure it feels real.
Immersive.

And as he’s looking at the designs, he’s playing with the calculator. Fidgeting.
TAK
He looks at the screen.
TAK CLAK
The screen looks at him.
TAK CLAK TRRRRAK

And he thinks –
What if we use this TAK sound on the website?
And in doing so, honor Curt’s memory in some absurd way.

A few weeks later

Gabriel’s at one of his local bars. It feels like an old lady's house.

There's a bartender there, a friend – Sofi. 
She likes Gabriel. She even invented a drink in his name, St. Gabriel.
A whiskey spice experimental blend thing.

And Gabriel tells her about all this.
And she says, “my boyfriend is a sound engineer.”

They rent a studio. 
A real studio where people record music. 
And they record the crisp, decisive, mechanical sounds.

Gabriel plays the sounds for his mom. She lays down on the bed, closes her eyes, and listens to each two minute recording. Over thirty recordings in total.

Over and over.
KAK. TAK. CLAK. TRRRRAK.
Until she goes… “THAT ONE!”
Rotula Resorte 2_01_clean.wav, 0:22 - 0:23.

And that was the end of the story. 

Until it wasn’t.

2024

The sounds of the Curta still live on our website sublime.app.

A few weeks ago from asks Sublime if we want to run an ad in his Internet Phone Book. 

Gabriel and I meet and discuss what it could be, and somehow the Curta sounds come up. 

And Gabriel tells me the story. 
And I say whoa.

And the sounds of the calculator born backwards in the mind of Curt Herzstack in 1930s Austria and almost given as a gift to Hitler, those crisp, decisive, mechanical sounds made by the only pocket-sized calculator people could use for about twenty years, those sounds traveled.

Those sounds traveled through the story told by Shl0ms.
And received by Gabriel.
And recorded by Sofi’s boyfriend.
And chosen by Gabriel's mom.
And added to Sublime’s website.
And shared now by me.
To you.

Those sounds traveled through us all, dancing and jiving and boogieing their way into our minds, hearts, and souls, sublime as they are.

~

A closing note

Do ideas have agency?
Do they crave to be shared?
To be reproduced, like humans? 

And if ideas have agency, do stories? 
Do we tell stories, or do stories tell us? 
Do we make sounds, or do sounds make us?

Does it matter?
Probably not.

Either way, our job is simply to listen.

And in listening, pay attention, be present, and make something wonderful.

We’ve been in a mood lately, feeling inspired by Mouthwash Studio: “everybody wants to have a village, but few are willing to be villagers.”

We’re taking it upon ourselves to create the scenes, be the inflection point, the reason interesting people find each other. Maybe one day, a Sublime cafe + library.

Until then, two events happening next week. Come through!

xx
Sari

How To Teach Machines Your Taste

with Emmett Shine

Online, Zoom

RSVP

​In this session, Emmett Shine (the creative force behind some of the most iconic brands of the past decade including Sweetgreen, Warby Parker, and Hims & Hers) will walk through a live example of what it means to move from using software to orchestrating systems of intelligence that encode taste, judgment, and principles.

​This is a rare opportunity to learn how one of the most influential brand minds is rethinking his craft in real time.

RSVP here.
Everyone who registers will receive the recording and materials afterward.

Tickets are $50.
But free for Premium+ members (code below the paywall).

Anti-Networking Miami

In-person, Miami

We are hosting an Anti-Networking night in Miami, in partnership with .

RSVP

If you cringe at networking events but you want to get out of your comfort zone, but you don’t want it to be awkward, but you still want to make amazing connections...then this is for you!

The space is incredible.
There will be light bites + drinks, on us.

As I am typing this email, there are 160+ people RSVPd and 50+ people on the waitlist. RSVP here and we’ll do our best to accommodate you.

If you’re a Premium+ member, reply to this email and we’ll make sure you’re taken care of.

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Today we’re publishing a beautiful conversation with Robert Greene.

Robert Greene is the bestselling author of The 48 Laws of Power, The Laws of Human Nature, and several other classics read by millions of people around the world.

After suffering a stroke that made typing difficult, he spent the last seven years writing a book about the sublime by hand.

In our conversation we talk about why our minds are shrinking to the size of phones despite the sublimity around us, the mystery of consciousness, his views on AI, how to reclaim a sense of awe in modern life, and lots more.

You can read the conversation below, listen on Spotify, or watch on YouTube.

P.S.

It took two years to make this conversation happen.

I first tried reaching out to Robert through the contact form on his website back in 2024. And then again the following year.

Eventually, through a bit of persistence and some help from Billy Oppenheimer, we got connected.

What I want most is to be a vessel for the sublime that’s screaming to be revealed in the world. In talking with Robert I felt in flow with something larger than myself. I hope that reading this conversation makes you feel something, because HOLY SHITTTTT WE’RE ALIVE!

*Best enjoyed with a cup of tea and this playlist ;)

The Age of The Sublime

A conversation with Robert Greene

—

Sari Azout: I’m very excited for this conversation. We both share a love for the word “sublime,” and I’ve followed everything you’ve put out about this book since you announced it. From the outside, it seems like this book is a shift from your earlier work, which is about power, control, domination, and influence. Did something change in you?

Robert Greene: Not really. I did a book with the rapper 50 Cent, The Laws of Human Nature, and the last chapter in that book was about confronting your mortality and was called “The Law of the Sublime.” So, I’ve written about it before. I understand the power book and the seduction book don’t seem very similar to this, but people are complex. I’m complex. I have several sides to me.

I remember reading about the sublime in the late 90s, there was a very famous book by a man named Thomas Weiskel that really shook me up. I thought, “This is an insanely interesting concept.” I’ve been fascinated by it ever since. I had meant to write this book in 2006, but other projects took me off that course.

Then I had a stroke in 2018 and came very, very close to dying. My wife saved my life while we were driving here in Los Angeles. The sublime and death are very much interconnected. I didn’t have a near-death experience, but I had something similar to it. I remember in the ambulance coming home from the hospital, and the experience was so jarring, so weird, and kind of marvelous in a way that I thought, “All right, the fates or the gods are telling me that now’s the time to write this book.” But it’s always been in my system. My books reflect the different aspects of my personality.

SA: How much of your calling to write it is personal versus a broader cultural observation of the spiritual hunger people have now?

RG: It’s a mix of both. Everything a writer writes is personal in some way, unless you’re writing a technical manual. But the book has a definite sense of purpose and mission. I feel like there’s something so soulless about our culture—something deeply, deeply missing in people’s experience of life, a kind of superficiality. Life is so weird and awesome, and there’s so much depth to it, but people, particularly young people, but really everybody with technology and a phone, are sleepwalking through life. It disturbs me and upsets me. I’m not judging it, because I have some of the same problems as well, but the book is filled with a sense of mission. I’m pushing myself against the trends of this culture and the times we’re living in.

On one hand, science is revealing an insane sublimity in this world. We now understand the first few minutes of the universe and the Big Bang; they’ve been able to photograph a black hole; we understand that life originated from the explosion of stars. All of these thoughts are mind-boggling, and science is revealing them. So, the paradox is that we live in a world where the sublime is exploding all around us in these discoveries, but people’s minds are getting smaller and smaller, constricting to the size of their phones. It’s personal, but I’m on a mission because I want to wake people up. I’m very disturbed by the way things are headed.

SA: If you had to name the things unique to modernity that erode our capacity to tap into the sublime, what do you think those are?

RG: There’s a kind of cynicism and disenchantment where people think the world is just the “brute facts” of life. They think anything having to do with spirituality, religion, or ancient cultures is just superstitious or irrational, which is absurd, because we’re not just here out of context. The religious aspect of life and the spirituality developed thousands of years ago is still within us. The thought patterns and the need for some kind of transcendent experience that takes you out of the banality of daily life—what used to be called the “sacred versus the profane”—is still there. We’re not suddenly “modern.” It’s still inside of us, and yet we’re denying it because we’re afraid of those animalistic, superstitious, irrational aspects embedded in our nature. We want to feel sophisticated, like we’ve come way beyond all of that. To be cynical and see the world through that disenchanted lens is now projected as being “intelligent,” which I don’t think it is at all.

SA: You said that when you had your stroke, you experienced pain but also a strange kind of happiness. I had something similar when my lung collapsed a few years ago while I was pregnant with my third child. I was in physical pain, but I felt an unexpected sense of connection to the world and to other people. It was like the physical pain made me more alive, whereas emotional pain tends to make me feel disembodied and stuck in my head. Do you think part of the “dopamine age” of living through our phones is that we’ve shifted from physical experiences of life to more cognitive ones?

RG: Yes. The last chapter of the book—which I just finished about three weeks ago after almost seven years of work—is about death. I looked into near-death experiences very deeply. It’s very common in the literature for people to say they’ve never felt so alive as in the moments they were facing death. It’s a very strange thing to say, but it struck me: it means when you’re “alive,” you’re not really living. Suffering and knowing you have only a week or two to live suddenly makes you feel more alive. The reason is that we live with this social mask that’s not very real. We’re always pretending, smiling, and saying things to please people. We’re always worried about our survival and how we’re going to make money. When that drops out, when you know it doesn’t mean anything anymore because you only have a few months to live, you suddenly feel a liberation. You’re free; you’re flying in the air. It’s wonderful. You’re rid of all that crap.

Social media is just a cesspool of those very petty things. I’m not saying it’s all that way—I have a meditation app on my phone that I love, but social media is mostly a cesspool of banality as opposed to these cosmic things. We’re conscious creatures, and we’re conscious for a reason. It’s a freak occurrence. I don’t even know if there’s anything else like it in the universe. It’s a thing you don’t want to waste. You’re only alive for several decades. You could die at any moment. That consciousness needs to be used for something beyond just what people are eating, or sex, or shopping.

SA: I have tasted transcendence through psychedelics and they’ve been very transformative experiences. But then the next day, there are still crying babies, payroll, and spreadsheets. We live inside a system. Can we simultaneously inhabit the mysticism and the spreadsheet? Is that the goal? I guess what I’m asking is: why is it so hard to integrate these ideas that we experience when we’re near death into everyday life?

RG: Well, most people who go through a near-death experience and come back say that it stays with them for the rest of their lives. They’re never the same after that, which is striking because I can’t think of any other human experience you could say that about. I’ve taken many drugs myself when I was younger, and they were amazing experiences, but they didn’t completely transform me. I don’t think therapy does, and I don’t think pharmaceuticals are going to do that. But death has that effect.

I’ve been doing Zen meditation for about 16 years—every morning, about 40 minutes of it. In Zen, there’s this idea that you reach a kind of ultimate enlightenment, and when you reach that stage, it’s complete integration with daily life. You can actually function in daily life on a higher level than when you’re so infused with the self and always insecure, thinking, “Are people thinking about me?”

When you get out of that, you actually function at a higher level. So if your baby is screaming and you have to feed it and you have all these banal chores, actually, the banal chores are part of enlightenment. You’re in the moment, you’re happy, you’re dealing with it, as opposed to worrying and being anxious and having all these recurring thoughts. This book shouldn’t be about a sharp delineation between everyday life and the sublime; it should suffuse your everyday experience and actually make you integrated on a higher level.

SA: It seems to me you don’t see exercising agency, having insane mastery over something—and dissolving the ego as contradictory things.

RG: Very much so. My fourth book was on mastery. The sixth chapter covers people who have mastered something on such a high level—usually music, the arts, or science—that it’s inside of them. It’s a mixing of the intuitive and the rational. When you reach that level where you’ve mastered the piano, for instance, the self kind of falls away and you become the keyboard; the piano is inside of you. You don’t have to think anymore.

Reaching that high level of performance in sports, culture, technology, or science means you’re not thinking anymore—you’re living. It’s inside of you and it comes out that way. It’s like you’ve spent the proverbial 10,000 or 20,000 hours working on something and it’s internalized. Your whole mental landscape has been transformed by all of this practice until you become the work itself. It’s an odd feeling, but when I’m writing, I feel like I am the words. I am the writing itself. It’s not me anymore. I don’t know if that makes any sense.

SA: It makes complete sense. And it also feels like that kind of immersion is much harder for creative people today. There’s this expectation of constant motion—optimizing for the algorithm, moving quickly, producing something all the time. You took seven years to write this book. Long-term thinking feels like a luxury now.

RG: I’m in a unique position because most writers are under extreme pressure to make a living. It’s very hard as a writer because you depend on royalties. I’ve reached a position for which I’m very blessed and grateful. I could choose this subject, spend almost seven years working on it, and not have to worry about living from paycheck to paycheck. Because of that, I was able to focus so deeply on one subject for so long that something unusual happens.

When you study great artists—and I’m not putting myself in their company by any means—but when you study a John Coltrane, a Bach, or a Picasso, their level of focus is so deep. People don’t have that luxury anymore. It’s so difficult. The levels of distraction are through the roof. You have to worry about paychecks, pleasing an audience, and making money; the pressures are extreme. I sympathize very deeply with that. I’m able to resist it because, quite frankly, I don’t care if anybody reads this book. I don’t care if it’s unpopular because I don’t need to worry about that anymore. But other people do. I think that’s a tremendous barrier that artists used to not have. I lived in New York in the early 80s when I was very young. It was a very strange time—the city was crime-infested and very dangerous—but there were artists all around. I lived in the East Village and SoHo, and people were living cheaply. They could live like that and make interesting art. You don’t have that luxury anymore. It’s very sad.

SA: There’s always a temptation to romanticize the past, but is there a moment in history that feels analogous to this? Where technology expanded so fast that it created a spiritual vacuum?

RG: It’s always a trade-off. There were things in the past that were very brutal and cruel, it’s not all rosy. If you read history, you understand that. Things move in waves in cultural history. It’s not a straight line where things just get worse and more banal; it goes up and down.

In the 18th century there was a reaction against religion and superstition. It was the birth of modern rationality—the Enlightenment. Writers, particularly in France like Voltaire and Diderot, were reacting against the irrationality of the Catholic Church. But then things descended into something superficial and banal, which led to an incredible reaction against the Enlightenment and this worship of human rationality.

That reaction came with Romanticism, a period when the sublime exploded. It’s the most important historical period for my book, because that’s when the sublime really became a modern concept. People discovered nature—the idea that nature itself is sublime, not just God or religion, but animals and the earth. It was a reaction against creeping banality and the worship of science. You had all this Gothic literature emerge because people wanted the mysterious and the superstitious.

My hope is that we’re coming out of something similar now. The Enlightenment wasn’t all bad—amazing things came out of it—but I hope we’re entering a moment where, in the next ten or twenty years, there will be a reaction like Romanticism or even the 1960s. Back then, people were fed up with the crushing banality of 1950s culture—Eisenhower, the “man in the gray flannel suit,” Madison Avenue. And then it exploded: hippies, flower power, psychedelics. These things move in waves. Maybe we’ll see a similar explosion again.

SA: We forget that this social media era is really just a twenty-year experiment, and the pendulums always swings. Right now, a handful of people: Mark Zuckerberg, Elon Musk, Sam Altman, have enormous influence over how we experience the world. If they read your book and were genuinely moved by it, how do you think it might change the kinds of products and experiences they enable?

RG: I remember in the early years of the internet, in the early 2000s, there was a kind of excitement. It was new. Something very interesting was happening where, for example, I might be interested in a particular jazz artist and suddenly see a whole community of people interested in the same thing. You could connect and make friends. In the beginning, the internet wasn’t about making money or constantly manipulating people; it was about connecting and opening up the world. Billions of people were on the same level. It was fascinating.

Technology had the potential to be absolutely sublime. If you think about the internet itself, it is a completely sublime object. Look at Wikipedia—it’s sometimes inaccurate, but thousands of people are working on the same thing and discovering it together. It’s mind-blowing. The sublime, in the original concept, includes what Immanuel Kant called the “mathematical sublime”—the sense of infinity and timelessness, the idea that our consciousness can become aware of the universe. It’s a concept you can’t really put into words or analyze because it doesn’t fit into any category.

The internet is infinite. It’s an infinite space. It could be a realm for exploring and opening the mind. Instead, it has become a tool for closing the mind.

There’s an interesting mystical writer I’ve always loved named Gurdjieff, whom I use in the new book. He had this idea that when anything is created—a religion, a political idea—it has a sparkle to it. It’s fresh and connected to life. But as time passes, it loses that spark and often turns into its opposite. Christianity, for example—a religion of love with Christ as this incredible figure—turns into its opposite over time. The internet was one of those things.

SA: I’ve read a lot of the work by the philosopher Byung-Chul Han, and one of the things he talks about is the the disappearance of rituals, and how transformative experiences often have boundaries, while the Internet is boundless. Right after this call, I’m hosting a fifteen-person Shabbat dinner at my home. I do it every Friday—it’s a ritual that gives my life meaning.

It makes me wonder: can technology be designed to create that kind of meaningful structure? Or is this the inevitable end state of American Capitalism and products shaped by the logic of markets and attention?

RG: Well, the thing is, I try to avoid turning the sublime into an abstract intellectual concept in the book. The sublime is an experience. It’s an experience of the world, not an idea. Because we live in all these abstractions, we’re so left-brain oriented—it’s all words and language. The sublime takes you out of that; it’s emotional.

The neuroscience of the sublime is very interesting. They’ve been able to map the sensation of awe and look at the brain as it happens. The sensation originates from the most primitive parts of the brain—emotional things you can’t really control. Then the cognitive side, the neocortex, sees that and starts analyzing it. In the combination of those two things, you have a sublime moment.

If I were to design technology like that, I’d want people to not be so passive. I’d want an app that makes you have an experience—hopefully a social one where you’re meeting people, like the internet used to do. I hope I’m not sounding too egotistical here, but if you took some of the things in my book and tried to make something where people could actually experience them, it would be powerful.

At the end of each of the twelve chapters, I have a section called “The Sublime Experience” where I give you exercises to bring this into your life. You walk around and look at the world a certain way, or you sit in a room and imagine certain things. I think I have about fifty of these exercises in the whole book. You could turn those into some kind of application. Instead of people passively consuming, I want them to have an active experience. If you could do that with technology, it would be wonderful. It’s very possible.

SA: We’ll get to some of the examples in your book, but before that I want to get into your views on AI.

RG: Everything is a tool. The internet is a tool; a hammer is a tool. A hammer can be used to build a beautiful home, or it can be used to kill somebody by clobbering them on the head. AI is a tool. I’ve used it myself—if there’s a quote I vaguely remember by some philosopher that I’d never find in the chaos of my office, I type in a few words and it comes up. It’s like magic. It’s insane.

SA: It’s sublime. I think the human-AI encounter itself—if you remove the fear of job loss and the existential anxiety around it—is sublime. It’s a miracle that we’ve made this.

RG: Yeah, but of course, like everything else, it reaches into the dark side of human psychology. And that, unfortunately, can be very frightening. I’m about to give a talk in a few days about how AI is going to completely disrupt the world economically. The people running it don’t have a great deal of responsibility; they’re under immense pressure to make money. It’s a capitalistic culture, and they’ve invested incredible sums of energy—literally energy, environmentally—so they’re under pressure to see a return. Because of that, they’re going to do things I don’t think are socially or humanly responsible. It could be dangerous.

On the other hand, the human brain is the most sublime organ of all. It’s more sublime than AI or the internet. Those things are simply reflections of the human brain. Our complexity is through the roof. Some neuroscientists have said nothing in the universe comes close to the complexity of the brain—the neurons, the connectivity, the infinite connections that can be made. Look at what we’ve done in a very short period of time, evolutionarily speaking. In 80,000 years, we’ve transformed ourselves into this.

It is the human brain that is so immense. When I talk about that intuitive mastery level, it concerns me that if young people aren’t learning to think or use their brains—if they become lazy because of AI—that is very dangerous. I don’t want to make out as if the past was always rosy, but I think of this example: My major in college was Classics, probably the least practical major you can have. I remember a crash course in Ancient Greek where we had to translate a paragraph by Thucydides. It took me a day and a half to translate that one paragraph. It was so frustrating; it drove me crazy. But it made me think. It made me develop patience. It made me realize that if I focus deeply, I’ll get there. It was a wonderful feeling. If you’re translating everything through AI and not learning a language, the brain will rot. Maybe it will develop in some other area, but I’m worried about the laziness it will infuse into our cognitive powers.

SA: Yeah, technology is neither good nor bad; it depends on what you do with it. I’ve used AI to think better, but I’ve also used it to outsource my thinking. In your view, how much of reclaiming the sublime is an individual responsibility versus requiring a collective shift?

RG: It’s up to you. No government or company is going to give you a sublime experience. It’s up to you to do that. If you take a bit of information from AI that is remarkable or miraculous and it makes you think—it makes your mind active—that’s fine. The mind can either be still or active; you can either consume “crap” passively or your mind can be tingling and moving. If you use that information to think, that is sublime. But I’m afraid that because humans are naturally lazy and tend to take the path of least resistance, it will have the opposite effect. I hope I’m wrong, but knowing human nature, the opposite could very well happen.

SA: I can imagine two possible futures. In one, we become more machine-like, and this “god” we’ve created simply raises expectations—making us busier and more disconnected from the sublime. In another, if people have the kind of intellectual freedom you have, AI could actually help them think more deeply and access that part of themselves. It feels like it could go either way.

RG: Very much so. People think too much about the technology; it’s really about the consciousness that interacts with it. If human consciousness blossoms and expands in the next few decades, it will use AI for those purposes.

As someone who reads a lot of history, I can’t say this is just a downward slide. There are moments where it goes down and then bounces back up. My hope is that young people—who drive change in this world, not dinosaurs like myself—are going to feel so bereft of experience and so bored with the culture the Boomers have fed them that they’re going to rebel. Youthful rebellion is a beautiful thing. We need it desperately right now. If that happens, there could be a new level of consciousness where people realize we need more experience and open minds.

Science is providing the tools for this. Neuroscience is fascinating; we’re delving into our own brains and uncovering things that are scary but also amazing. If we take what science is giving us, it could lead to an explosion of the sublime. I remember reading about the evolution of life—understanding that three billion years ago, there was just bacteria in the ocean. You follow the evolution, the extinctions, the moments where new creatures evolved, and you can’t believe we’re here.

If an asteroid hadn’t struck Earth at the exact angle it did 60 million years ago, dinosaurs would still be here. Because of that cataclysm, mammals could evolve and become dominant. If that hadn’t happened, I wouldn’t be talking to you; there would be pterodactyls in the sky. We live in a world suffused with this knowledge, yet it’s not affecting people. In one chapter, I mention that if we actually thought about how unlikely it is that you, Sari, exist—with all the things that happened in evolution and your parents meeting—we would be building temples and synagogues just to worship the fact that we’re here. Science might be destroying the planet on one hand, but on the other, it could be expanding our consciousness.

SA: You said something that resonated with me: technology doesn’t change the world—people do, depending on the consciousness they bring to it. It often feels that everything is available today, yet nothing feels profound.

I grew up in a small city in Colombia called Barranquilla, and I remember discovering TED talks and the internet when I was about twelve. If you had told me then that one day I’d carry a device in my pocket that could answer any question and connect me with anyone, I wouldn’t have believed you. And yet here we are, and it feels like our consciousness hasn’t caught up to the technology.

Your book feels like a spiritual wake-up call, and I appreciate that you are trying to make it practical. What are some practices people can bring into their daily lives?

RG: Some of it is as simple as taking a walk and changing how you look at the world, because the sublime is a perceptual thing. It’s how you look at the world—it’s not that the things themselves are sublime, but our brain and our consciousness are aware of them. A lot of it involves walking around and looking at things as they are, divorced from the words we associate with them.

If you look at a tree and don’t think of the word “tree,” you see this giant thing springing up out of the ground from nothing with all these leaves on top. What is this weird thing? It’s very strange. Or you look at the sky and see clouds—and you don’t think of the word “clouds,” but you just see the thing itself: these fleecy white things against a blue sky. They’re weird, they’re insane, they’re strange. There’s probably no other planet in the universe where people see clouds quite like this.

Most people don’t truly “see” the things around them. So many of the exercises are about changing perception. I’m also trying to get you to move away from these values where some things are worth looking at and others aren’t. I’m trying to get you to think that everything is equal. That’s one of the exercises: ants are as interesting as people; dog excrement on the ground is as interesting as a beautiful building. It’s all the same level. If you get rid of all your judgments and gradations of what’s “great” and just see the whole thing on the same plane, that changes everything.

SA: The first one you described is exactly how my four-year-old experiences the world. When we walk into a room, he finds everything fascinating. Meanwhile, I’m in an efficiency mindset, just trying to get from point A to point B as fast as possible.

RG: Well, one of the twelve chapters is about the “Childhood Sublime.” One reason we’re aware of the sublime—and why we’re so miserable sometimes—is that we remember when we were two or three years old and our minds were different. Everything was new and exciting. We weren’t experiencing the world through words; we were seeing things as they are for the first time. In the back of our minds, we know we had that and lost it, which makes us very depressed.

In that chapter, I explain how you can reclaim it. You can re-experience your childhood—not through some magic, but by recreating how children see the world. It’s a capacity you have; great artists are capable of it. I talk about Vladimir Nabokov, who was obsessed with his childhood because he was separated from Russia and couldn’t return. He went so deep into the experience that he saw the world through the eyes of a child. Childhood is our first real experience of the sublime. Because you were pre-verbal, you experienced the world directly and immediately.

In the last chapter on death, I have an exercise that’s a little frightening where I try to make you experience your own dying. Because I’ve researched it and lived it, I know what happens to the brain and body as things start dissolving. I try to take you through that process as you lie on the floor and feel yourself dying. Then, at the point where it’s “gone,” I ask you to walk outside as if you’re a ghost—as if you’ve been granted one last walk. This is the last time I’m going to see the sky; this is the last time I’m going to see a bird. Suddenly, things look very different. I’m trying to move death away from being an abstract, boring philosophical discussion and show that it is a physical and spiritual experience. You’re conscious as you’re dying—at least some people are—and it is an awesome, amazing experience.

I talk about Carl Jung, who had a near-death experience in the 40s. He describes it in such beautiful detail. He says he experienced death from the inside, and it’s not the same as death from the outside. From the outside, it looks like you’re just dying, but from the inside, you’re being reborn. I’m trying to give you that sensation. I don’t know if I succeeded, but that was my goal with that exercise.

SA: You’ve been writing this book for seven years. How did writing it change you? More specifically, how did it change your ability to experience the sublime?

RG: It was an insanely arduous process. I can’t begin to describe it to you because I could not type—and I’ve been a fast typist since I was nine years old. How do you write a book without typing? I had to hand-write everything. It was really difficult. I’d have to dictate it into the computer, print it out, edit it by hand, and then dictate it again. I was trying to be inspired while dealing with all these physical limitations.

When I first thought of writing the book twenty years ago, I was going to go to the Gobi Desert, the Amazon, and swim with dolphins. I was going to have all these experiences and write about them. But now I’m writing the book and I can’t do any of that. I can’t even take a hike to clear my mind. I’m trapped in this room.

That was a blessing in disguise because it made me realize the reader also has limitations. How can you experience the sublime when you can’t travel? When you’re in Brooklyn and it’s snowing and ugly and dark? I had to experience that sitting in my office. I had to experience it watching my cat and looking into his eyes. I had to go into my backyard and just sit in a chair, looking at the nature I had right there, not up in the mountains. It changed me because to make the book exciting, I had to transform myself so I could feel the sublime in everyday things.

SA: That is very very inspiring. I can’t tell you how excited I am to read this book. It feels to me like we are re-entering the age of the sublime.

RG: Well, maybe when it comes out, we’ll revisit this. Thank you, Sari. I really enjoyed it.

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Elan writes the newsletter Escape the Algorithm and teaches a course by the same name at the University of Pennsylvania, where he helps students explore what creativity looks like outside the gravitational pull of feeds and metrics.

We are always looking to collaborate with people who have a certain Sublime “-ness”. Elan is very much one of them.

This edition is brought to you by Squarespace.

If you want a personal or professional home for your ideas that isn’t entirely dependent on “The Algorithm,” may I suggest you build yourself two foundations:

1. Sublime to deepen your thinking.

2. Squarespace to present it with intention.

A workshop and a gallery, if you will ;)

You can view a draft of my personal site here. It’s pretty bare bones, but Squarespace has a whole universe of features I intend to explore… you can sell products, make yourself findable with SEO tweaks, add emails flows, and more. That’s the nice thing about having your own corner of the web: you can do whatever you want with it.

If you need a personal website, portfolio, or storefront, Squarespace is perfect.

Click here to try it out, and when you’re ready, use code SUBLIME to save 10% off your first purchase of a website or domain.

In today’s conversation, speaks to the writer, illustrator, and cartoonist , whose work has been published in The New Yorker, The New York Times, and Buzzfeed. Amongst other things, she discusses the emotional rollercoaster of making art on the internet, the rise and fall of Instagram for artists, and what happens when a creative project succeeds as a vision but fails as a business.

You can find a full collection of resources mentioned and highlights from this conversation in this Sublime collection.

What would you say is your relationship with “The Algorithm?”

My first thought is resentment that teeters into begrudging acceptance, similar to my relationship with reality. It just is. There have been times I’ve benefited from the algorithm, and times it’s rendered me nearly invisible. Seeing myself in relation to it can be very frustrating — like banging your head against a wall — because I don’t want to tailor my work to an algorithm.

At times I’ve felt like I’m making work in a vacuum and having identity crises, but it’s also been a reminder to focus on the work and focus on art as communication. 2011–2015 on Instagram felt like a golden period. I was supported at a time when I was a young, fragile artist. Maybe it was the lack of an algorithm. My work got seen, I got a platform, and then around 2017–2018 it plummeted and has kept plummeting. I’m making the same work, I’m the same artist. I’ll post a drawing and twenty people will see it out of 100,000 followers.

I’ve heard you say that when you publish something, you’re frightened by your own desperation for approval. Does that still resonate, and has it dissipated or been heightened by being less visible online?

I don’t remember saying that, but it’s true. This gets complicated quickly. In 2022–2023 I stopped sharing much of my work and turned inward. It felt like silence and invisibility.

More recently I’ve come out of that through Substack: sharing work in a new place, with a new algorithm. It isn’t as simple as “I just have to believe in myself and that’s enough.” I literally made a mirror behind me that says “I believe in you.” I was trying to summon self-belief, but that doesn’t capture communication.

The desperation for approval is the frothy top layer: “I hope people like it.” Beneath that is a deep desire for communication, community, and understanding. If I were the last person on Earth, maybe I’d still make art, but it wouldn’t be the same. There’s an essential ingredient: expressing something and having it be witnessed by others, having people say, “I see that too.”

On the old Instagram, the wheel would get a full rotation: it’s out of me, it has a life, someone tells me what it meant to them or it made them laugh. That’s a huge reason I make art. It isn’t fully done without that.

I want an audience. The idea that it’s only about belief, likes, and approval is one piece of something bigger: wanting my work to be part of a wider conversation. My lesson from Instagram is to hold platforms loosely. If the audience dips, don’t let that stop you. It’s jarring to go from thousands of likes to twenty, deep into your career, but it isn’t personal.

We’ll probably leapfrog platforms forever. I’ll be shocked if Substack doesn’t enshittify. The question is how to protect your work from someone else controlling the applause button. Making work through the ups and downs of algorithms has strengthened my resolve. I turned inward for years; it all lived in sketchbooks. Then I shared again. That’s part of it.

When I emailed you about talking about something meaningful that failed in the marketplace of online attention, you immediately knew you wanted to talk about Halmart. Can you tell me how that project got started?

I believe it was 2021. I’d been running an online shop for years. I used a basic local printer; I did little projects: pet portraits, and I got an ID card printer like a gym uses and printed “artistic licenses,” little licenses to make art. The shop was a repository for ideas, and it started making enough money that I sat up and thought: I’m barely trying and it’s working. I thought what if I tried? It was easy, and I saw that as a problem. I wondered if I had other ideas I’d never realized. So I closed my shop for a year and built a new iteration: Halmart.

It was everything I dreamed, and it was really hard. I engineered physical objects. I made a “now” clock that ticks and every number says “now.” The work was enormous: talking to clock parts people in Canada, and multiplying that by every product. I made pillowcases, the mirror, found a printer for archival-quality prints. I made everything the most beautiful version it could be.

The website was a masterpiece: I worked with my friend Jesse Vaughan. I wrote and co-directed two infomercials, went to prop houses, got friends to act. I can’t describe how much work it was. I didn’t linger on the fact that the shop would launch and then I’d have to run a shop. But it was satisfying to make things real — to turn sketches into objects and share them with the world.

Other than the income, what would the shop succeeding have represented to you?

It was an online representation of myself that was glossy: the best, most colorful, fun, beautifully photographed, silly version of me. I’m amazed by people with tailored online presences. I’ve always been scrappier: my website is ten years old and I haven’t updated it. Things don’t match, I draw in different styles, I don’t have uniformity. The shop was like: “This is Halmart, I am Hallie, look how cute.”

But that isn’t me. The thing I took for granted — my old store where I’d say, “I got a gym ID printer and I’m making cards” — was more me. I’m proud of what I made with Halmart, but it was me wanting to see myself as fully realized.

You told me that when you showed people products in person, they said they’d buy them, but when you launched the shop, most of them didn’t.

I thought two things. First, the boom in 2021… we all had pandemic bonuses. It was a famously spendy time. I didn’t clock that. I thought: I have a lot of potential.

Second, I was enticed by realizing a vision. I clicked into that zone. I made choices like nicer paper, even if it cost more. I wanted to be a fancy artist lady people pay a lot for, because everyone says, “You’re worth it! Charge more!” I still see influencer videos about undercharging.

But I tried the fancy version and it didn’t work. People didn’t want the nicer thing. They wanted the $25 print they can tape to the wall. The artisanal, museum-quality thing satisfied me, but I was trying to value my work in a different way, shepherd it into an era where I’d be more valued.

Then launch happens, and suddenly I’m a girl who runs a shop. Then there’s more product. I realized how constant the promotion is. Constant.

Do these platforms position your work in a way that makes people expect cheap work or cheap prices?

I don’t think it’s necessarily my work, but I do fall into “commercial artist.”

I’ve never been in the fine art world. Even when I make drawings without words, they resonate less. I put original drawings and paintings on my site and thought: why shouldn’t this be $500? Other people do that. But essentially, I’m a commercial artist, and most things are cheap now. If someone can go to Society6 and get a $15 print from an amazing artist, why would they buy mine? They don’t care about paper or museum quality.

Expectations sometimes get set for you. You can try to steer yourself into a different category. I was exploring: can I control this, can I declare value? Someone thinks something looks like a child drew it; someone else thinks it’s an original David Shrigley worth $15,000. It’s all made up, so why couldn’t I do that?

When I priced my shop, I tried to resist undervaluing my work. I asked: if I walked into a fancy gallery and saw this, what would I pay? That painting behind me is by Esther Pearl Watson: amazing illustrator, zine-world cartoonist, makes books. She’s in galleries now. Why not me? I was pushing myself in that direction and learning lessons.

Are you saying putting your work on Instagram makes people not see you as a fine artist, or is it about how Instagram’s algorithm sees you compared to fine artists?

My impression from fine artists I follow is consistency and restraint. It doesn’t seem confessional. It isn’t a place where you post videos talking about personal stuff. I’ve talked about personal stuff.

I remember talking to a friend who went to art school for painting. She said fine art is about the art but also a lot of branding. One teacher told students to pick a haircut and stick with it so you’re recognizable.

My art doesn’t look the same; I change my hair. When I created Halmart and tried to contain myself in a beautiful box, I was valuing traits I don’t have. Looking back, what I want to take forward is that ease isn’t a problem. When you’re gifted at something, it feels easy and you take it for granted. You start thinking struggle indicates quality.

Now I try to notice where the water flows — where energy naturally pours. When I created Halmart and told myself “try so hard,” everything was a struggle. You tell yourself you’re glad you did it, because otherwise you’d explode.

What happened to the shop?

I decided to close it in summer 2023, right around the time I got pregnant with my twins. I could have kept running it. I ran it for around six months, and I felt completely run down by posting: buy this, link to this. That felt awful, and it didn’t feel like communication. I felt like I was selling to my audience. I wanted it to be worth it, wanted it to succeed, but I didn’t want to do the work to make it succeed.

How did it feel to shut it down?

Such a relief. I’m happy about how quickly I stepped aside. As soon as it clicked that I didn’t want to be a shop proprietor — that it’s a full-time job suited for a different type of artist — I was done. I felt bad because I looped in people who helped me but I had to say: I was wrong about my dream. I didn’t want it.

That’s why it isn’t simple to call it a failure. Did it sell amazingly? No. Did I also not want to do it? Yes. I like the making part. I want that to be most of my work. I didn’t fully understand that when you have a shop, your main work is selling; the rest becomes frustrating gridlock.

If there was a failure, maybe it was in the fact that you created an idea of yourself that you didn’t want to inhabit for longer than six months.

Yeah. I’m good at making art. I’m okay at sharing it and sometimes selling it. With books, the book finds its audience if there’s one there. That tells you something. The book I’ve made that’s most successful is What to Do When I’m Gone with my mom in 2018. It has had a long life. I know because I hear from people: “I give this book to everyone.” I made the work, and it just reaches people. I’m not posting every day on Instagram.

Moving forward, I want to make work that matters to me and tell stories that matter to me. The work is at my desk, giving myself space to write and draw, having conversations and sketching. That is the work.

One of the things available in Halmart was a print of your “It’s a Miracle We Ever Met” illustration. Can you tell the story of the genesis of that?

When I’ve talked about it, sometimes I say it’s about everyone I’ve ever loved. I don’t have one memory associated with it, but I remember being with my little brother Nick on his birthday one year, sitting by the ocean, thinking: I can’t believe how crazy it is that we’re from the same family that out of everything, out of a bajillion sperms and eggs, it’s the two of us, and we’re hanging out. I don’t know where the image came from. Sometimes stuff drops into your hand or sketchbook. I didn’t set out to make it; it appeared.

Sometimes I’ll make a new friend and I’ll give it to them. It does feel astonishing to connect with anyone in this world. The rarity can be taken for granted, and it felt nice to visualize that.

I’ve seen many versions of the illustration in the wild: low-resolution screenshots of screenshots. Some that are copycats, the same illustration with different captions. Knockoff illustration with the same caption. People tattooing it on themselves. How does it feel to see your work become a meme?

I don’t think anyone’s asked me in this way. It’s interesting because I just described it as something that showed up, and it’s cool to reflect on that.

For the first few years, as it started to run away from me, I was reactive. I remember around 2019, Deepak Chopra’s Instagram posted it without credit. I got upset. I’d link to them, people would pile on and shame them. I was trying to hold on to it. I’m not saying “everyone go steal it,” but there’s a point where someone will DM me saying something’s a rip-off, and I’ll say: whatever. It was so long ago; I’m making new work now.

It’s crazy that something I made resonated so much that someone got it tattooed all over their body without having any idea that I made it. Would I love credit? Sure. But spending my current moments guard-dogging old work is not the best use of my time. It’s nice when someone can connect and find my other work. My job is to focus on what I’m making. I’ve done my time pearl-clutching that the internet is a garbage heap. I’ll just make some new garbage.

I’m obsessed with the idea of this illustration as a commentary on itself: it’s a miracle that it finds anyone, given the sheer magnitude of all that exists online. There are two ways to greet that miracle: with awe at the attention and labor that went into it, or by shrugging it off as unexplainable and contextless.

When I said earlier that one lesson of Halmart is holding things lightly, letting things have ease, paying attention to resistance… have you heard of Bread and Puppet? It’s a Vermont-based activist puppet theater. I learned about it recently and saw them perform in Cincinnati. It was in a big church; tons of families; donation-based. They performed with huge puppets, a dragon filling the room. We got a $2 print of the Cheap Art Manifesto:

When I’m sitting there thinking, am I fancy enough, am I worth this or that, I’m participating in “art as business.” Any time I’ve slipped deep into the business side, it’s been miserable. That said, it’s a privilege to not be hustling for money.

But I like the Bread and Puppet ethos. That’s why I don’t charge for my Substack. I feel honored that anyone spends time with my work. What I value most right now isn’t money — it’s communication, community, shared understanding. After years of being contained in my sketchbooks because Instagram was so inhospitable, I crave communication. Even you writing to have this conversation is an example: I want to share reality together. I crave that more than anything right now.

These days, you can support Hallie’s work by subscribing to her free weekly newsletter HALMAIL, by following her on Instagram, and buying her books or prints. Also, she’s teaching a micro-memoir retreat in Spain this fall! And there are still a few spots available.

You can follow more of Elan Ullendorff’s work by subscribing to Escape the Algorithm.

If you want a personal or professional home for your ideas that isn’t entirely dependent on “The Feed,” may I suggest you build yourself two foundations:

1. Sublime to deepen your thinking.

2. Squarespace to present it with intention.

A workshop and a gallery, if you will ;)

I put together a draft of my own personal site last night, which you can view here. It’s pretty bare bones, but Squarespace has a whole universe of features I intend to explore… you can sell products, make yourself findable with SEO tweaks, add emails flows, and more. That’s the nice thing about having your own corner of the web: you can do whatever you want with it.

If you need a personal website, portfolio, or storefront, Squarespace is perfect.

Click here to try it out, and when you’re ready, use code SUBLIME to save 10% off your first purchase of a website or domain.

Welcome to another edition of “What’s in the Cards?” where we share 10 things that made us go whoa:

1. This Joni Mitchell cover song, my God!! Prince also did an incredible cover of this song.

2. I like this definition of intelligence: “The only true test of intelligence is if you get what you want out of life.” It follows then that “AI fails it instantly because an AI doesn’t want anything out of life. AI’s desires are programmed by the human controlling it.”
   
   *Moment captured using Podcast Magic. If you tried it months ago, it’s way better now. Podcast Magic is a one-time $20 payment for unlimited moments. This is early believer pricing. You can upgrade here.

   

3. Had to read this one several times to understand it, but wow, Tina is such a gifted writer. She manages to do several things in this piece: explain how modern AI training works, use that as a metaphor for different kinds of human minds, and turn it into a spiritual question about what we’re optimizing for.

   Fakepixels

   Pre, Mid, Post-Training Way of Life

   "For here there is no place / that does not see you. You must change your life…

   Read more

   4 months ago · 48 likes · Tina He

4. Sublime’s target audience:

   

5. The new Mumford & Sons album, which my friend described as Blockbuster bluegrass that still feels played from the front porch. You can hear the miles on his voice.

6. Option 3.: Consider the possibility that building the next phase of your career around the fear of getting left behind might be a really bad basis for producing the kind of work people will want to pay you for.

7. This but Delaware franchise taxes are due today.

8. A theory about nostalgia. Pair with this note from Tammy Winter and this one from Adam Mastroianni.

   

9. You can focus on your art. Or you can focus on the space, narrative, and marketing for your art. Don’t sleep on the latter.

10. Love a good 2x2 chart. Here’s a collection of more.

    

For Premium members below the paywall—a sneak peek + invitation to beta test a new way I’ve been thinking with my library.

Read more

1. Last week’s event with Lucas Crespo on building a brand identity using your taste + AI absolutely delivered. Members, scroll down to get the recording + assets.

2. Gabriel and I will be at Plant the Future in Miami this coming Tuesday from 11am-2pm. If you’re around, stop by for complimentary tea, a peek at what we’re working on at Sublime, and a chance to give feedback / hang with us!

Some brief thoughts on starting a company/project in these insane times.

I kept this draft open throughout the week and every time I read the bullets from the day before I wasn’t sure I agreed anymore. It’s a confusing time to be a person. Tell me some of you also feel this way?

• Every decision is a tradeoff.
  
  The people who love Sublime love that we’re not pushy, it’s there when they need it, respects their attention, and doesn’t beg to be opened. But the people who wish they used it more say they forget it exists.
  
  Give this data to ten founders and they’ll make ten different choices. One adds streaks, push notifications, daily reminders. Another looks at the same data and says: the reason our best users love us is because we don’t do that. You can rationalize any path.
  
  I really love this from Axel Dumas, the CEO of Hermes: Strategy is accepting that you are doing something better than the other and the other is doing something better than you. You have to pick your fight.

• Small is hard. Big is hard.
  
  They’re just hard in different ways. Being small means you have to defer ideas you’re excited about. You go slower. You realize doing something well takes almost the same energy whether ten people see it or ten million. But being small also means we can do things simply because they feel right. We can make candles. Send emails like this. There’s no ego. No decisions by committee. In life and business, you don’t get no constraints. You choose your constraints.

• Self-doubt kills more ideas than competition or lack of funding ever will. If you want to make the world a better place, tell someone building something you love you believe in them.

• AI has made a lot of parts of building a company easier. It’s also made other parts harder.
  
  I can upload a CSV and get data in ten minutes that used to require a full-time data analyst. I can ramble into ChatGPT for ten minutes about a feature idea and end up with a coherent PRD in Linear. But these things are easier for everyone else too.
  
  The hard parts are still stubbornly human: deciding what is worth doing, inspiring people to care, the last mile of building high craft products, the slow work of building a community. The people-y things.

• Two conflicting perspectives I’m trying to reconcile: having a clear vision is critical, but the difference between success and failure is usually in getting a thousand unsexy details right. It’s tempting for founders to see problems as strategy problems when they’re really execution problems. I’d rather be thinking about where Sublime is going in five years than why a tweet didn’t embed right.
  
  The emotional range of going from “what is our reason for existing” to “this button is in the wrong place” is its own special kind of vertigo. I think this might be The Skill? Balancing thinking big with executing small.

• Regrettably, the founder-as-influencer thing works.
  
  I don’t know if this is true for all products, but a meaningful share of how people discover Sublime is through my podcast appearances, long-form writing, and talks.
  
  The part that frustrates me isn’t being public. What I struggle with is the cadence. The things I want to say and make take time. I don’t want to hit “send” on something and immediately cringe because it doesn’t feel like me. I don’t want more stuff that’s here today and gone tomorrow.
  
  I haven’t yet found a satisfying way to bridge the content creation demands of running a modern business with a pace that suits my sanity. I worry about “work hard on something you love” metastasizing into “work hard to keep pace with the machine.”
  
  I’ve come to accept the trade-off: slower (albeit more durable) growth in exchange for not hating what we put out into the world.

• I keep seeing some version of: why would I pay for software if I can just prompt it myself?
  
  Every hype cycle produces a lot of hot takes and confident predictions. This has the same energy as “everyone will 3D-print everything at home.” People underestimate how hard it is to build software that works reliably, handles edge cases, feels intuitive, earns trust, and carries real weight.
  
  What I think will happen is the bar for software will rise. Single purpose tools will fall out of favor. Increasingly, people will expect their software to work as a system, not a collection of disjointed tools.
  
  Nobody wants just a bookmarking tool. They want to save the things that moved them, find them again when it matters, put them to work in a creative project, and stumble upon something new and interesting along the way.
  
  Right now, people are duct taping different tools—read here, save there, think about it somewhere else, google it again three weeks later. The software that survives this era will be the one that eliminates the need for five others. The irony is that while everyone is talking about how easy it is to build software now, those actually building software are finding it harder because the bar is higher.

• Becoming comprehensible is the single biggest challenge for anyone building anything today.
  
  The limiting factor isn’t what is technically possible, but what people can absorb and understand, with the time and attention they are giving you. Being comprehensible is highly context dependent, which makes problems of comprehensibility much harder. What someone has tried before. What’s broken for them. What problems they’re carrying. What they’re ready to see. There’s no one clean, correct version of an idea that will make it click. The distilled version that sticks for you isn’t the same that sticks for me.
  
  This is also the bind: the most valuable thing you can build is a system, but the easiest thing to explain is a single-purpose tool.

  
  

• I think companies will tell you what they want to be if you listen.
  
  Sublime wants to be an independent, boutique software tool + membership for people who care about ideas, creativity and craft. The quirky mix of software, events, zines, etc… it feels very us.
  
  People who know me say this is the most me thing I could be doing. Carve out our lane and chill? It sounds funny but I think it’s a sensible business strategy? Why compete to be the best when you can be the only?
  
  Here’s Forest and Mike after this week’s event on building a brand identity using your taste + AI (no slop allowed):

  

  

If you made it this far and you’ve been orbiting Sublime for months (years?), what are you waiting for? A Sublime annual membership costs less than the two lukewarm Uber Eats sandwiches you definitely could have made at home.

For that, you get your own searchable library of every interesting thing you come across (essential if you make creative work for a living), a community-curated search engine that is not drowning in SEO garbage, and no-BS events with the most inspiring builders and creatives we know.

Just saying… this might be the most underpriced membership on the internet. ¯\_(ツ)_/¯

Join here.

For members, below the paywall: the recording + assets of last week’s event with Lucas Crespo on How to Create a Brand Identity Using Your Taste + AI (No Slop Allowed).

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He reduced it to a single line:

Taste + AI = Impact

Here’s the chart I had made:

How cool it is to have someone truly listen, take in your story, and then help you simplify what it is you are really after.

Mental fog comes not from lack of insight but from an excess of it. Smart people are uniquely vulnerable to mistaking complexity for insight (… the ten page memo that could be one). Complexity drugs us with the illusion of wisdom.

Back to the formula…

Taste + AI = Impact

I think at the heart of it…that’s what I’ve been simmering on for years now.

A lot of people talk about AI as a productivity upgrade. Faster this. Faster that. But that framing has never clicked for me.

AI is powerful, but power without direction is like a hamster spinning on wheels without moving forward. Taste is how you wield these tools to create work that matters.

This is the future we are building toward.

We’ll keep building the best tool to help you curate a living library of inspiration, and actually do something with it. We’ll keep hosting events to learn how to wield AI with taste (and just as importantly, when not to use it).

At the end of the day, we still believe in aspiring to greatness. In measuring success by the quality of what we make, not the number of tasks completed.

~

For Sublime Premium members, below the paywall, the clip where Greg snaps this idea into focus.

Plus an invite to a live session with Lucas Crespo, one of the people I’m most drawn to using new tools to create aesthetics that feel alive and original. You’ll watch Lucas create a brand identity using a handful of references, and tools like Claude Code and Nanobanana.

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1. Unbelievable flow state and unbelievable sounds. I’m a happier, less anxious person after listening to this!!

   

   
   

2. is my favorite essayist on the internet right now. His essay on Text is King is great. This line was a favorite. (Bonus: I have a full curated collection on text as a medium here)

   

   
   
   

3. A provocative essay arguing that the anxiety around AI is concentrated in a specific, prestige-oriented class that values abstract, language-heavy thinking.

   

   
   

4. I agree, and would add the skills we think make us irreplaceable might not be the ones that actually do. A related essay I loved: Rizz is the new intelligence

   

5. “It has to be different, even if it’s worse” is a crazy sentence. Captured using Podcast Magic.

   

   
   
   

6. The incentives of the industry you’re in shape your mood.

   

   
   
   

7. 2026 Macro Trend Report by

   

   
   

8. An internet listening bar designed by Charlotte Taylor, and the Poolsuite team. Very cool project!

   

Plus, below the paywall, for Sublime Premium members: access to a private collection of great cold emails + an RSVP link to a session with next week on how to write an unignorable emails. We’ll write some together live!

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Today, we’re sharing an essay by longtime Sublime member and cultural strategist on resisting algorithmic sameness, excavating your own perspective, and treating research as a form of pattern disruption. While his work lives in the world of culture and trends, the ideas in this piece apply to anyone trying to think clearly about anything today.

idle gaze

Research as a form of pattern disruption

The industry of cultural futuregazing, once a niche subset of ‘coolhunters’ in the 90s, who began tracking street-born trends for brands, has evolved into a sprawling industry. This year alone, 135+ trend reports were published by tech companies, agencies and consultancies. Today, anyone with a TikTok account or Substack and a penchant for digital decod…

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3 months ago · 15 likes · 2 comments · Alexi Gunner

It’s also a love letter to a slower way of thinking and to using Sublime <3.

If you’ve ever felt rushed to have an opinion before you were ready, this is for you.

Enjoy ;)

Research as a form of pattern disruption

There are more trend forecasters, futurists and TikTok oracles than ever. So why does our idea of the future still feel so devoid of nuance, inspiration and possibility?

By • JAN 15, 2026

The industry of cultural futuregazing, once a niche subset of ‘coolhunters’ in the 90s, who began tracking street-born trends for brands, has evolved into a sprawling industry. This year alone, 135+ trend reports were published by tech companies, agencies and consultancies. Today, anyone with a TikTok account or Substack and a penchant for digital decoding can become a trend forecaster. Some refer to it as a whole new class of content creators - what fashion search engine Lyst has coined ‘vibe analysts’: “info-influencers acting as digital spirit guides to the next big thing”.

Yet, despite this abundance of enthusiasm for cultural research, it often feels like it’s easier than ever to slip into the gravity well of banality. Cookie-cutter essays optimized for algorithmic engagement. Hot takes stripped of depth. Fleeting fads interpreted as extreme, paradigm-shifting hyperbole. We resort to dramatic binaries, either painting the future through the lens of stressful dystopias and exclusionary utopias.

The limitation of our vision is not due to insufficient data. Instead, what I think we’re missing is a sense of imagination, creativity, and genuine curiosity. Without these elements, the act of research itself has lost its potency, our findings and interpretations reduced to a shallow performance, where the same ideas are recycled and repackaged in an endless feedback loop.

In this essay, written in partnership with Sublime, my main personal knowledge management tool, I’ll share how I approach research as a form of pattern disruption, an intentional practice for breaking free from the hall of mirrors that traps so much of today’s trend forecasting. I’ll walk through how I use Sublime to collect, connect and create meaning from information in ways that resist the common shortfalls: confirmation bias, surface-level analysis, and the pressure for immediate answers. It’s an approach that embraces discomfort rather than absolute certainty, curiosity rather than conclusions. Fuelled by a desire to explore the unknown, to go down deeper rabbit holes, I believe the greatest research skill you can have is, indeed, “being a nosy b***h who wants to find out“.

Tuning in to weird signals

In the world of trend research, we are traditionally taught to be on the lookout for ‘weak signals’ - small, low-frequency indicators that hint at a potential shift in culture. And while scanning for these weak signals is a fundamental part of the process, it’s easy to get stuck in a pattern of only noticing evidence that confirms our preconceived notions about the world. We develop tunnel vision, unconsciously conforming to the ideas and beliefs that dominate the zeitgeist of any given moment.

Instead, what I have trained myself to look for, more specifically, are ‘weird’ signals. Weird signals are behaviours and phenomena that feel strange or out of place. But importantly, they also tend to hint at unanticipated future cultural upheavals. As cultural futurist Jasmine Bina explains: “weird signals usually give us a glimpse into the future we can’t see yet. Every major cultural shift that changed our lives once started as a small anomaly in the system.”

It’s easy to avoid these uncomfortable anomalies, because they create cognitive dissonance. But by embracing discomfort and attuning ourselves to weird signals, we can begin to spot unexpected and alternative realities that are vastly different from our current day.

In William Gibson’s 2003 cyberpunk novel Pattern Recognition, the protagonist Cayce Pollard, a coolhunter and creative consultant, utilises her body’s visceral reaction to the world around her to detect irregularities and deviations. Like Pollard, spotting weird signals requires us to tune into our nervous system to cut through the noise to find glitches in the matrix, embracing the discomfort that comes with stumbling across the peculiar.

Glitches in the system, like punk birding groups, and luddite teenagers promoting self-liberation from social media and technology. ‘Or the rise of ‘homebars’ across China, designed to replicate the experience of living together with friends, and the emergence of study raves in Australia, helping students to focus through high-energy beats.

Weird signals can take the form of almost anything - snippets from articles and essays, images, social media content, a conversation on a podcast. Sometimes, it’s a strange meme that hints at an emerging shift in our collective mood, societal worries, and desires.

To spot weird signals, you need to go down rabbit holes. Follow your intuition. And remember, pursuing rabbit holes is not always an act of procrastination. Sometimes, it’s simply your mind telling you to follow your curiosity. Weirdness can present itself at any given moment, through any medium. When I see something, I instantly save it with the Sublime web extension. Or I use the Podcast Magic app to capture soundbites from interviews and podcasts. Like an eager digital forager, I highlight, screengrab, upload, and save with reckless abandon whenever strangeness presents itself.

Avoid algorithmic rabbit holes, because they will dull your exposure to weird signals and trap you in a bubble. To spot anomalies, you need to escape your Instagram feed and FYP page. Don’t let social media platforms shape how you see the world! A lot of work goes into manually curating my information feed. Read widely, and actively. Follow interesting researchers who publish on Substack. Lurk in the dark forest of Discord servers, where fringe conversations thrive.

When I’m foraging for signals, I don’t worry too much about organisation or classification. With Sublime, unlike other PKMs, you don’t have to incessantly tag it to find it later. With a solid AI search engine, it’s easy to find things you’ve previously saved. Instead of tags, I’ll intuitively create a collection for the signal that frames an initial hunch about whatever you’ve captured (or save it to an existing collection if an instant connection presents itself in your mind).

Spotting non-obvious connections

At regular intervals, I’ll return to my research on Sublime, to sort, reflect and connect. After all, collecting without connecting is just hoarding—a library full of signals collecting digital dust.

Traditionally, I’d use a variety of pre-defined tags to start to make sense of the signals. What sectors are involved? Psychographics? Relevant markets? Maturity level? Underlying need states?

I’ve often felt that this approach to organising research tends to guide you towards a more linear, stale way of making sense of trends. It funnels you towards drawing connections between similar signals, across interlocked domains in culture. Like uncovering a trend that encompasses food, drink and hospitality. Or identifying a new, emerging tech sector. Not wrong, or inaccurate. But perhaps a little obvious? And with so much homogeneous thinking out there on the future of culture, obvious holds little value.

With Sublime, instead of traditional tagging, I’ll curate research by specific questions or theses. Perhaps it’s a provocation, or a question I’m aiming to explore, or a shower thought about the future of culture. But it’s always based on an intention. Something specific I’m personally intrigued by, or niggling problem I’m trying to explore for a client.

What if we reintroduced more friction into society? Resolving the loneliness epidemic through third spaces. What comes after the hipster? The death of mystery.

Arranging research into these broader, more abstract themes encourages me to go non-linear, embracing expansive, freeform sense-making. Suddenly, it’s much easier to connect dots between vastly different areas of life to explore the defined intention. It invites me to find connections across a multitude of subcultures and demographics. Across both mainstream discourse and the experimental fringes of society. From highbrow and lowbrow culture (and everything in between).

There are also ways to tap into the wisdom of the crowd to find the non-obvious. ‘Save one idea, discover 100 related ones’ - Sublime’s discovery engine that shows you related cards in the Sublime database - helps me to uncover new ideas and quirky tangents related to my collections. Recently, a collection I’d built around the death and rebirth of nightlife unearthed a post exploring the rise of fluid, fragmented, and decentralized clubbing communities beyond the massive entertainment venues that have otherwise come to dominate nightlife worldwide. An idea was hand-saved by a real person, which sent me down an unexpected but wholly relevant rabbit hole.

Once I’ve gathered these disparate signals, and go from collecting to connecting, I need to work spatially, using mind-mapping tools. Usually, this is Miro or Figma, but recently it’s mostly happening in Sublime’s Canvas function, where I can automatically create boards that link to my collections. This is what makes Sublime unique compared to other typical bookmarking tools - there’s a seamless bridge between curating information and creating meaning, where I can automatically create boards from my collections, giving me space to draw arrows between information, scribble tangents, and cluster research. This way, I can make far more interesting connections and create coherent meaning from all the noise. It syncs up new cards added to the collection, so you can keep coming back to the board as the research grows.

Machines for breadth, human intuition for depth

Sean Monahan, co-founder of K-Hole and writer of the 8Ball newsletter, recently argued that, with the advent of AI, the human trend forecaster will become obsolete. I disagree. What I think will happen instead is that LLMs will raise the standards for our trend research. Machine and human sense-making operating in tandem, expanding what’s possible and helping us break free from our filter bubbles.

AI offers breadth - it aids me in cross-referencing unprecedented amounts of disparate information sources and millions of data points. With Sublime’s ‘Chat’ function, I’ll export particularly big collections to my LLM to kickstart the sense-making process, or when I feel overwhelmed by the sheer amount of research it contains.

Meanwhile, my own cultural intuition offers depth - it helps me to identify emotional nuance, uncovering unexpected angles to a trend. What’s the opposing force that exists in tension? What’s the uncomfortable angle that needs to be acknowledged? How would an outsider see this differently? What’s the destructive or distressing dimension?

Zoe Scaman calls this new breed of centaur analyst the ‘synthesized strategist’: “They wield AI like a sixth sense while maintaining razor-sharp human judgment. Most importantly, they’re masters of synthesis – weaving together insights from multiple domains, perspectives, and tools to forge clarity from complexity and light new paths forward.”

Resisting immediacy

“In an age of speed, I began to think, nothing could be more invigorating than going slow. In an age of distraction, nothing can feel more luxurious than paying attention. And in an age of constant movement, nothing is more urgent than sitting still.”

In the art of stillness, Pico Iyer argued that in our madly accelerating world, there’s never been a greater need to slow down. There is a similar urgency for stillness in cultural research. We are living through an era where trend cycles move at hyper-speed, compressed into 24-hour cycles. Every day, there’s a new shiny fad, a new viral moment, flocks of forecasters and oracles eager to crown them with a new catchy title, in an attempt to drive engagement and visibility in the feed. Yet, these isolated spikes flatten the story and miss deeper patterns. As cultural theorist Matt Klein astutely points out, we are “conflating trends with what’s trending”.

The fact is, culture moves slowly. Sometimes, painfully so. What starts as an anomaly gradually accumulates into a pattern, eventually entering the mainstream zeitgeist itself. It’s these slower-moving undercurrents I’m interested in. The subtle drifts beneath the media hype cycle that fundamentally shape how we behave, connect, consume, and express ourselves. These currents only become visible over time, as signals accumulate and the ground beneath our feet shifts, almost imperceptibly.

A movement challenging people to go offline forever becomes part of a bigger story about the great rewilding. ‘Scream clubs’, at first seen as a quirky anomaly, shape up to become one of the many ways we fulfil a desire for collective catharsis. Purposefully dirty makeup, initially a temporary beauty fad, begins to tell a broader story about our exhaustion with the pressures of modern life.

In strategist Nikita Walia’s critique of TikTok oracles, she argues that cultural commentary today favours brevity, at the cost of depth, algorithmic performance over exploration, virality over rigor. All of which prioritize speed and instant output: “rather than a participatory culture that deepens understanding, we have one that accelerates interpretation at the expense of complexity, where discourse is less about discovery and more about domination.”

Amid this competition for algorithmic domination, where there is pressure to constantly decode and make meaning from the 24/7 internet hamster wheel, I have to remind myself to resist this manufactured immediacy. A PKM like Sublime helps me slow down and take a far more iterative, contemplative approach to cultural research by encouraging me to treat my collections as digital gardens.

When you think of your research as part of a digital garden, it’s less about solidifying and publishing thoughts across my Substack and client work as part of a linear process, in the hope of being the first to classify a cultural phenomenon. Instead, it becomes something far more slow, fluid and organic, where broader trends and undercurrents are continuously revised, and nurtured as the proof and signals grow over time. Deeper, more nuanced layers begin to reveal themselves, and a broader story takes shape.

My collections will evolve over time, as they grow. Many of them are now several years in the making, taking on new shapes and meaning. I also acknowledge that they may go through periods of rot and weeds, during which I must choose to actively prune irrelevant signals or change the direction of the collection entirely. I put time in my calendar once a month to tend to my gardens. In contrast to the usual frenzy of client work, the gardening feels mindful, quiet, reflective - a digital equivalent to touching grass.

Excavating your own perspective

There’s a quote saved in my Sublime library that I think about all the time: “research is the sacred ritual of excavating your own perspective”.

Ultimately, this is the end goal of my cultural research. It’s chipping away at all the chaos, uncertainty, and mystery, tuning into weird signals, making non-obvious and expansive connections across a multitude of domains. It’s about embracing a slower sense of reflection, until a path forward begins to illuminate itself. A vision of a new potential future that feels vastly different than our current reality. Not shaped by the echo chambers of the internet, but one that has taken shape through my own process of self-discovery.

2025 was the year everything became available, and almost nothing felt meaningful.

So I thought what better way to start the year than to ask: What did you encounter in 2025 that truly moved you?

We asked 33 of our favorite people this question.

Share yours in the comments!
Or add it to this community Sublime collection.

P.S. If Sublime has been a place you return to, I mentioned in my end-of-year video that the Founder’s pricing on the Lifetime plan is live for a few more weeks. Get 25% off with code LASTCHANCE.

What did you encounter this year that truly moved you?

Escaping Flatland

The third chair

From Ivan’s Childhood (1962) by Andrei Tarkovsky…

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2 years ago · 436 likes · 24 comments · Henrik Karlsson

The third chair by . It’s a short (~400-words), beautiful story of Henrik returning to the place he long persevered—through doubt, despair, loneliness—in doing the work which brought the circumstances of his current life into existence.

It surfaced memories of my own past and, with them, a gratitude toward my previous selves I hadn’t felt before. And then the last line—it made my arm hairs stand up. It’s so good. It resists the writerly urge to overly explain or spell out the takeaway, and trusts that the reader will pick up what he’s putting down.

—Billy Oppenheimer (a researcher and writer who works closely with Rick Rubin and Ryan Holiday)

“U2 + Gospel Choir - I still haven’t found what I’m looking for”

—Nicole Ripka, Collab Fund

Rats from Rocks

Mother

Why do you want to write about your mother…

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a year ago · 219 likes · 81 comments · Mills Baker

One of my favorite essays of the year was this one from the inimitable —an homage to his late mother:

My mother could be reduced only to the scale of climate: you could not call her the sun or the rain or an ice storm or a hurricane, and nothing anyone has calculated or computed would generate accurate predictions about her. I think it’s fair to say that no one ever knew her, which made many want to. [...] ​Like me, she was very good in a crisis and very bad on a typical weekday; I believe it was she who introduced me to Walker Percy, even taking me to Covington to see where he lived, and he was well-aware of this reality: “It is easier to survive a category five hurricane than it is to get through an ordinary Wednesday afternoon.” My mother was defeated by Wednesdays.

— , writer

Shrek Retold (2018) I’ve heard the lore, but never watched it until recently.

Shrek Retold is a full re-creation of Shrek by 200 storytellers, each recreating a snippet of the movie in their own style.

An impressive feat in itself, for me, the film put cooperation and creativity on full display. You can just do things. Especially fun things. Especially unnecessary things. And especially together.

—,

Would you laugh at me if I said Heated Rivalry? I think there was something freeing about watching something so earnest.

—, meme artist at Nostalgia Express

I'm a lifelong Paul Simon fan and saw him live for the first time last July in Davies Symphony Hall in San Francisco. He played his latest album, 7 Psalms, straight through. It's a lovely, meditative, seeking composition - his "death" album.

Then he played the hits. There was a special energy in the building. Paul Simon is 84 years old. Everyone including him knew we were seeing him for the last time. He was small and frail and sang like an angel.

He played a generous four song encore that ended with Sound of Silence. We gave him a standing ovation that lasted forever. We poured our love out to him, thanking him for a lifetime of music that has come to feel like an old friend.

The entire night was magical and life-affirming. (And the small serving of mushrooms didn't dampen my emotions...).

—Ben Springwater, founder of Matter and Halo

“Four Talks” by Laurie Anderson at the Hirschhorn Museum in Washington D.C. A full room installation in which every surface is painted on with wisdom/provocative jokes. Monumental in terms of actual size, as well as the three-dimensional way it represents an artist’s brain. What it can/look/feel/be like when you let go into the dream. At the complete other end of the spectrum I think about “Guitar” by Mac DeMarco, an incredibly unadorned album that’s one of the realest things I’ve ever heard, and a daily listen for half the year. The songs are great and the guitar playing deliberately basic and emotive (try “Punishment” and “Nothing At All”) while Mac lays bare his heartache. The whole album has an honesty and authenticity worth aspiring to whatever your practice. — , Metalabel

In 2025 I encountered the book To See Takes Time, a collection of Georgia O’Keefe’s lesser known work, and it was extremely influential as I started my business two months postpartum. There is a shell in the book she drew hundreds of times.

Not to perfect it, but to stay close to it and get inside of it. “There is a fascination about trying,” she said. Trying as in: returning, starting over, and being dedicated enough to “keep circling the pencil until it speaks back.”

—

I loved seeing this painting in person. It used to be my desktop background in college.

—, Dirt.fyi

This year I started making a documentary about a man who lost everything—his car, his house, his family—but still takes the train every day to the library to work on his horror film script. Watching him choose creativity over despair reminded me that making something is the most defiant form of hope.

—Nate Stranzl, Director & Producer

I’m semi-obsessed with my shirts from @itsashirt.

Small batches, locally produced.

—,

Seeing Helen Pashgian at The Getty.

It’s raining in Los Angeles and I’m crying at the museum. Uncommon for me, but apparently not so uncommon for this installation. I wandered in by accident, but once I was there, I couldn’t tell you how long I stayed, in awe of what was unfolding in front of me.

A great Light and Space artwork, Pashgian’s especially, is like a visual koan. It short-circuits the logical side of your brain in the most beautiful way, freeing you from it. Your mind can’t quite grasp what it’s seeing. It’s always just around a corner, just out of reach. In that pursuit, you’re suspended in the moment with it. It's like a vacation from the ego. Temporary self-transcendence.

For me, that defines these rare moments of aliveness. Being so consumed by something that the boundary between you and the moment disappears. It reminds me of this quote by Ray Ascott: “Stop thinking about artworks as objects, and start thinking about them as triggers for experiences.”

—,

Scuba diving the White Wall in Fiji—a dramatic underwater cliff face of luminescent white coral. It’s a deeper dive and feels absolutely surreal, like exploring another planet.

Also: diving with manta rays at a cleaning station.

They look like slow, gentle space aliens, and I got to hover alongside them, observing their grace and movement through the water. Both experiences remain vividly etched in my brain.

—,

Things become other things by Craig Mod.

I love reading books where you can feel that the author poured their heart and soul into it.

—,

Reading about Michel Majerus painting during the first internet era.

It reminded me how alive the AI era feels when I’m making things.

— Marc, Danger Testing

In 2025 I fell in love with the techno producer Polygonia’s Dream Horizons album: wide-ranging, intensely spatial electronic music that drifts in and out of consciousnessness like a dream.

I read two novels that reaffirmed the importance of humor, lightheartedness, and sincerity in the pursuit of one’s values: Mushtaq Ahmad Yousufi’s Mirages of the Mind (1990) and Zoe Dubno’s Happiness and Love (2025).

Dan Wang’s Breakneck is a brilliant nonfiction book, but I also read it as a guide for how to do good work—immerse yourself in the process, make long-term plans, and execute like an engineer (but don’t forget compassion!).

—,

This is the year I learned that love and loss come together, and that our greatest pains are the path to deeper love. A couple of days before the year ended, my friend Ophelia sent me this episode of Modern Love with Andrew Garfield, in which he reads Learning to Measure Time in Love and Loss.

It was bizarrely good timing, like a summary of what had been on my mind, expressed beautifully.

—Lola Wajskop, Asylum VC

Life Together by Dietrich Bonhoeffer

— Reggie James

I'm an avid reader—primarily fiction; give me your high school reading curriculum and I'll devour it. I read because it takes me out of the day-to-day of running a company with 3 small children at home.

This past year, I read a book called Trust by Hernan Diaz that lives rent free in my brain. The book is magnificently written as the same story told from 3 perspectives. It captivates the reader, doesn't tire, and you can't put it down.

The ending is so powerfully unexpected, it causes me to pause and reflect every so often about the unexpected twists in my own life.

I can't recommend it highly enough.

—My friend Ellen DaSilva

I was moved by the kindness of new friends this year.

Becoming a mom, there were so many moments that touched me and reminded me of the simple grace of generosity. Practically, the meal train a girlfriend set up will move me until the day I die.

—,

Annie Dillard’s “Pilgrim at Tinker Creek.

Part nature writing, part philosophical meditation, “Tinker Creek” consists of fifteen chapters inspired by dozens of journals Dillard kept in the early 1970s to record her solo walks around a valley in deep, rural Virginia.

There is no real plot to speak of. Most chapters revolve around Dillard heading out to the creek and just waiting. For a muskrat to appear, a praying mantis egg to hatch, a morning light to cast its mountain shadow. “Tinker Creek” is, without question, one of the hardest books I’ve ever read. And also one of the most impactful, because it’s taught me the value of seeing—not just beauty, but also ugliness.

Both are unfolding around us constantly, on scales big and small, whether we sense them or not, and something started changing in me when, like Annie, I tried to be there for all of it, even the moments that were painful.

Here’s the piece I wrote in response.

— , Sana

Two things moved me to think about life this year.

One was traveling to Taiwan to see my grandmother, who is 87, for the first time in six years. Between the pandemic and having young kids, the long gap happened unintentionally, yet I still regret it. At one point she told me, plainly and without much emotion, that because the trip is so long, I shouldn’t feel pressure to come back if anything happens to her. I keep thinking about that, and whether it was her way of showing love by trying to ease a burden she could already see coming.

The other was Tatiana Schlossberg’s essay, “A Battle With My Blood.” What moved me wasn’t just her fight with cancer, but reading about someone with a full, beautiful life being forced to look at it directly… to sort through memories, habits, and days while still living them and quietly take stock of her life. Her words made the present feel exquisitely and painfully delicate in a way I can’t quite shake.

—My friend Joy Chua

What moved me in 2025 was the film Sinners.

Despite the incredible pace of change in the wider world, so many things (products, blogs, cultural artefacts) I came across last year didn’t feel original.

The starting point for Sinners isn’t, either; the myth that blues legend Robert Johnson traded his soul to the devil in exchange for his uncanny musical abilities is a universal story humans have told each other for centuries, back to Dr Faustus in the Renaissance.

Layered on top of that is a deep south Black vampire movie about gangster twins who return triumphantly to their hometown to set up a juke joint…until night falls. I watched it for the first time sitting in an old-fashioned cinema in the Mission in San Francisco and found it totally original; from the showpiece scene that speaks to the transcendence of really good music to the repeat theme of the hard trades we make to build lives we want—which spoke to me deeply.

I’ve watched Sinners twice since and it’s made me cry every time.

— Sarah Drinkwater, Common Magic

Is it strange to say a zombie movie gave me the most feels this year? In the final moments of 28 Years Later, the main protagonist says a heartbreaking goodbye.

During this emotional scene, Ralph Fiennes’s character reminds him with the words “Memento amorous,” which means “remember you must love.”

Whether in my work as a writer, or in my much more important roles as husband and father, I tend to overly focus on my task. I burn my emotional bandwidth on making sure I’m regulating myself enough to keep getting shit done. But that “memento amorous” electrified me in theaters, and reminded me that love has to be the organizing principle, the thing everything else serves.

Otherwise, what is the point? Again, I recognize that zombie slasher flick is a deeply weird way to have a profound realization about the meaning of life, but that’s the movies for ya baby.

—,

What truly moved me this year were the calls I have been doing as part of The GrownUp Table, my free mentoring program for women and new immigrants.

—, Interintellect

In A Natural History of Empty Lots Christopher Brown (of the newsletter) finds simultaneous apocalypse and rebirth in the pockets of nature that thrive in urban edgelands.

And in the way that a good metaphor can become a tender seedling in the asphalt of ideas, it also gave new language to my own work: searching for organic life in the wreckage of the internet.

How thrilling! What a gift the mixture of language and attention can be! I am certain you’ll find anything but emptiness in its lots as well.

—, Escape the Algorithm

The little kid I’m watching as I write this: crouched under his dad’s legs—a man three times his size—trying to lift him up for a piggy back ride; Lonesome Dove; that Lily Allen album; the end of a relationship, the start of another; teenagers jumping from Monhegan’s dock into the wharf to send off the ferry; watching two pigeons kiss on the subway tracks; sitting across from a trio of baby bangs on the B48 and feeling old for the first time; “Maybe happiness is the wrong measurement.”

—,

I believe I read both Watchmen and From Hell at the start of this year (time is hazy these days) and was struck by both.

Watchmen is probably one of the best novels I’ve read full-stop and, though I’d heard it was incredible, I was still really astonished by its narrative depth and psychological acuity.

From Hell has possibly stuck with me even more, though I think it’s not quite as soaringly good. Still, the way that Moore paints his grimy characters haunts a few corners of my cerebellum and I will find myself in London occasionally staring at a Hawksmoor church and thinking that work.

—,

Among 2025’s surprises was a new pope. By taking the name Leo XIV, he deliberately echoed Leo XIII—a pope who stared down industrial upheaval and tried to give ordinary people a moral compass for a changing economy.

What moved me wasn’t his grasp of this awesome technology or its accompanying high stakes, but the quiet clue he offered about how he plans to live in the midst of it.

In an interview, he mentioned a small, old book—The Practice of the Presence of God—about turning normal life into prayer, attention, and steadiness. One line keeps following me: “Blind as we are, we hinder God, and stop the current of His graces.” That’s the whole modern problem in a sentence. Per E.O. Wilson, “We are drowning in information, while starving for wisdom.”

In 2026, I want to practice the one thing AI can’t automate: interior attention. No matter your religious practice, the invitation lands: make room for God’s presence in our lives.

—,

2025 began with 22 friends and colleagues losing their homes in the LA fires.

After the initial shock, what stayed with me most and moved me the most was how people responded: the generosity, the creativity and then the resilience.

I watched them all make something livable, and even beautiful, out of a terrible situation and it reminded me that all we need is our health and each other.

—, Ghia

I had the chance to attend Frieze Soul, where I encountered The Language of The Enemy, an exhibition by Adrián Villar Rojas which occupied all four floors of the Art Sonje Center: “Emerging at a moment when humanity teeters at the edge of its own continuity, Villar Rojas’s work inhabits the liminal space between extinction and inheritance.”

—,

Last year I found my great grandma’s old diaries, they ranged from the moment she met my great grandpa until they got married, which was 16 years being together without a ring—from 1911 to 1927.

As you may imagine, my great grandpa wasn’t the best man, he brought much pain to her and my family, but reading about it made me infinitely grateful for the fact that I have the freedom and independence she never had.

Additionally, she was a writer—as much as she could be during that time at least—so it has been a privilege to read these entries, allowing me to connect with her and see myself within the words she wrote over 100 years ago.

—,

Last fall, I ran a half marathon through New York City with 200 strangers.

Two hundred crazies in running shorts treating the streets like our personal track. A local running club organized it the night before the NYC Marathon for everyone who didn’t get in.

We met near 125th with no course markings or finish line. Just a handful of checkpoints and the understanding that some of us would run 12.3 miles, others 13.9, depending on which way we turned.

We cut through Central Park in the dark, down Broadway through Times Square, weaving between Halloween costumes and delivery drivers who looked at us like we were insane.

No permits, sponsors, or medals — just a bunch of people who love to run.

What moved me was the simplicity of showing up for something that exists just because someone decided it should. It reminded me why I started running in the first place. And that there really is no place like New York.

—, Off Menu

And lastly my answer:

Without a doubt, my first psilocybin journey.

Since then, I’ve become deeply curious about consciousness and the sense that the everyday plane of awareness might only be a tiny sliver of what’s available to us.

That curiosity led me to reading An End to Upside Down Thinking by Mark Gober. The idea that consciousness might be non-local to the brain has held a grip on me ever since. It feels so good to have a question.

Maybe this is also I was so moved by Rosalia’s latest album, which she described as having verticality, a desire to get closer to the divine.

—

So I tried to do the same for Sublime. I hit record and talked through this past year.

If you use Sublime, I think you’ll enjoy seeing the inner workings —where we are as a business, how we grow, how we’re feeling, etc… And if you’re an ambitious builder trying to create with a different relationship to time, you might feel mirrored here.

Mostly, I just want to say thank you for voting with your hearts and wallets for us to keep doing this work. Know that we don’t take your trust and attention lightly.

Beaming you all warm + sublime holiday wishes!

1. My conversation with David Pierce, Editor-at-Large at The Verge

2. An invitation to an end-of-year Sublime gathering

1/

I went on The Vergecast and talked to David Pierce about my vision for Sublime and my thoughts on AI. There are parts of this episode where I wish I was clearer and went deeper. I am brewing a post where I state my views on some of these topics more clearly.

Until then, here’s the episode.

I can barely listen to myself for ten minutes but Henrik said he could listen for 10 hours.

2/

To close out the year, we are gathering the Sublime community for a live end-of-year movement journey, on us.

It’s a live online session of mellow yoga, breathwork, meditation, and reflection to step into the new year with a sense of awe, groundedness, and sublimity.

Details:
꩜ Date: Wednesday, December 17
꩜ Time: 12:00 PM EST
꩜ Length: ~45 minutes + optional hang-out writing time
꩜ Where: Online (Zoom)

The experience will be led by Allegra Preuss, a yoga and meditation student and teacher. She also writes for fun @, is a devoted curator of a fantastic Sublime library, and the creator of the infamous guided dance ceremony “The Jellyfish Jam.”

RSVP

It’ll be fun, hope to see you there :)

<3

1. The founder of MSCHF, Gabe Whaley, on the diminishing returns of virality and the value of building longer-term relationships with smaller engaged audiences. Captured using Podcast Magic. Related ideas in the goal is resonance, not scale.

   

2. If I had the time, I would write a book about how wrong we’ve been about what we consider intelligence. (More musings on intelligence here.)

3. Only two Deadline Candle studio packs left. Get yours here!
   

   
   

4. Easy to think you have to be doing your biggest and best thing all the time. The truth is you simply need to stay in the game long enough. Many more musings on long-term thinking here.

   

5. 10/10 slide deck by . Essential reading for anyone working in social, brand, and creative. Can tell he saved receipts throughout the year. Did someone tell him about Sublime?

The rest of this newsletter is for Sublime Premium and Lifetime members-only.

Also below the paywall: a private RSVP link to our session next week on how to make a zine people will buy with designer–publisher Itay Dreyfus (NICHE DESIGN). If you’ve been curious about sharing your ideas in print and bringing your work into analog form, this session will be rich in details.

Read more

The Deadline Candle is available in limited quantities as:

• A single candle

• A studio pack of 10 candles

It has always seemed to me that productivity discourse tends to have a desiccated vision of ambition. So much of productivity is fueled by negative emotions. You’re afraid of falling behind, so you attempt to build elaborate systems and workflows to fix yourself. There’s no joy in it. No soul.

The Deadline Candle was inspired by this note:

Creativity dies with too much structure. But it also dies without deadlines. A deadline prevents you from trying to make something perfect, so you have to make it different. Different is better.

Get the Deadline Candle.

Enjoy ;)

Get the Deadline Candle

!! As seen on 2025 holiday gift guide for tech people with taste ;)

!! And on @kylemakesshortfilms’ Instagram

SHOP NOW

Plus here’s a moodboard on rituals. Enjoy :)

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This conversation with the one and only Kevin Kelly is the final bonus interview for Whoa, Vol II: Conversations on AI x Creativity.

Kevin Kelly is the founder of Wired and my personal role model for what a well-adjusted, intellectually, spiritually, and creatively nourishing life looks like. wrote an exceptional profile of him, which is worth reading in full here.

In this conversation, Kevin shares:

• How he’s using AI in his creative process (what it’s good at and what it’s not)

• Whether 1,000 True Fans still works for creators today

• What he thinks people will pay for when AI can make “good enough” anything

• How he would build Wired if he were starting today

• The platform that is becoming the center of culture (and that most creators are underutilizing)

• His new book Colors of Asia, which he describes as “cool and useless”

• And what he’s most excited about right now

This conversation is an exclusive perk for Sublime Premium+ and Lifetime members (and paid newsletter subs, if you prefer our relationship be mediated by Substack). To read the full conversation, become a paying subscriber.

Alex Dobrenko: There’s a lot of conversation right now around AI. And what we’re not seeing as much is, how are people actually using it? Or what are the concerns people have about it taking away their creative livelihood? Let’s start there.

Kevin Kelly: I use it a fair amount and I’m not very worried about it. I will say that the more powerful the technologies are, the more powerful the problems it will create. So I am expecting AI to be one of the most problematic technologies we’ve ever made while being the most powerful one that we’ve ever made.

And my formula is that if we can create just 2% more than we destroy every year, that 2% compounded over time is what progress is. So there will be a very, very long and big list of all the problems with AI, but the list of what’s good is a little bit longer, not by much. So I’m not going to argue that there’s no problems, there’s plenty of problems, but as long as the solutions and the benefits outweigh it by 2%, which is not very much, it’s hardly even visible.

And the other thing I would say is there’s something I call thinkism, which is this idea that we can solve things by thinking about them or that we can even understand things by thinking about them, that what the world needs is more intelligence. We’re not going to solve or even identify the right problems by thinking about them. We only figure it out through use.

So your question of how people actually use it is the most important question because that’s how we’re going to figure out what’s good and bad. Not by thinking about it, not by imagining what could happen. That’s important, but it doesn’t go far enough. It’s just the first step and we’re now at the second step. And the second step is that you have to actually look at how we use them and what the actual harms are versus the imaginary harms. The actual harms are pretty minimal so far.

Very few people have lost their job to AI. Very, very, very few people. There might be a lot of people who may not be hired because of AI. That’s a second thing. But very few people who’ve been fired because of it. I think it’s really interesting that if you ask people about their own jobs, whether their own jobs could be replaced by AI, nobody thinks their job can be replaced by it. But my friend of a friend... their job is going to be replaced. It’s like, no, it doesn’t work that way. So, anyway, I can’t say I have no worries about, there’s lots of things to be concerned about, but there’s more to be excited by.

AD: What excites you about it lately?

KK: Well, let’s talk about what we have right now versus what we could imagine. It’s very clear that an AI that reads everything is really, really good at answering questions. I’ve been trying to get it into the habit of asking it every question I have. It’s stunning, its ability to kind of answer any question.

But, how much does that change my life? Well, I mean, that’s been a lifelong dream to have the answer machine, where you can ask anything. So I would say, there’s a 7% satisfaction improvement in my life. As someone who likes to learn, that’s a 7% increase in satisfaction. So that’s one thing. It’s like Google plus in terms of doing the daily things that we do better and sometimes things that I couldn’t even do before. So I don’t know how to rate that improvement. It’s not 10x, but it’s better.

There’s that part of my life, using it like a research intern, and it’s amazing. When I left Wired, I had a little tiny bit of money that I got out of the sale of Wired. And I did not buy a boat. I did not buy a house. What I used my money for was I hired a full-time researcher 30 years ago.

And I’ve had a full-time researcher all this time. Research has always been a really huge, important thing to me. The research capability of AI is really great. However, I still have my researcher and they’re using AI. And so they have been 5x’d. I think their productivity is about 5x because now my researchers are using AI to do research. So that’s good. That’s really good.

In terms of creative stuff, I did a one-year private analog art project, once a day. And then I did a year of AI art with mostly Midjourney. And that was fun. And I learned a lot about some of the limits and the capabilities.

And recently I’ve been trying to take a graphic novel that we had made, a really huge one, and turn it into a movie by feeding the panels into Sora and Vio. That’s been very frustrating because it’s just not quite there yet to actually do something that’s releasable.

I use generative AI a lot. Whenever I do slides, I generate the images for the slides using AI. When I do a post, I generate the images. So these are things that are accelerating or they’re increasing the quality of what I had been doing rather than enabling something new. Generating the movie from the panels, that is new. But that’s been very frustrating. I haven’t gotten very far with that. It’s just not quite there yet in terms of total control that I need.

I am working on a project right now where I did a bunch of generating still images and I am going to be producing three-dimensional artifacts from them. I was struggling for a while with that workflow, and I just finally had someone help me and I’m going to start. I’m going to be printing them out initially just on my 3D printer, but finally I’m going to be using a color, I’ll send them out for a full color, three-dimensional thing.

So I’m doing some art where I produced the final thing as physical analog art that comes through the AI generation workflow. But they’re going to be physical artifacts. And I’m really excited by that. And so I’m about halfway in kind of proving that and getting the workflow done. And it looks like I can do it. I think the tools are now close enough that I can probably make that pretty automated workflow. And so I’m going to be producing these analog physical objects rather than just little pictures. I’m really excited because it’s my year of analog art. I’ve kind of decided I’m going to do as much analog art as possible.

I did a whole saga of a series of 10 books, a counterfactual history that was really cool that I do not intend to show anybody because I realized that the joy of co-writing it and co-creating it was more joy than reading it. I don’t think anybody would enjoy it as much as I enjoyed co-creating it. So I wrote this piece called “The Audience of One,” which is this idea that I think mere co-creation will fuel a lot of the use of AI in creativity, where you like doodling or sketching, diarying or taking a walk. It’s the pleasure of that moment of doing it and creating it. That is the main benefit.

AD: Which is so interesting to me because I write on Substack to an audience, and I don’t know how to write without an audience, you know?

KK: Yeah. Well, that’s interesting. And I understand that, but there may be other things that you might want to do other than write where maybe you’re going to sketch or you’re going to design things or you’re going to make other things where you don’t need the audience.

AD: Totally. I think this veers a little bit into something else I wanted to talk to you about, which is the way that for people in my generation, and it seems like younger too, there’s this sense of: anything I do must be shared and monetized, because that’s sort of my way to my thousand true fans, right? All roads kind of lead there somewhat. And I’m curious to talk to you about your One Thousand True Fans thesis. How do you feel about that almost 20 years later? Do you still believe in that? I think a lot of people want to know from you, what is the magic rule now for success?

KK: I think the mathematics, the arithmetic around Thousand True Fans still works. It’s something that I said pretty early on, I think in the second version of the piece, which I haven’t changed my mind about, and that is it’s not for everybody.

It requires a set of skills of managing, overseeing, interacting with people that some creatives don’t have and don’t want. So it is nearly a full-time job tending your fans. And not only is it even for the people who might work for it, it may only work for a certain period of time. It’s a great place to start. Doesn’t mean you have to end up there, but it’s a great place to start. And many people might start there and then move on to something that’s more mediated where they have other people involved or they have labels and studios or publishers.

So for me, the important thing is that it’s an option, an alternative to the only route that was before, which was a bigger and bigger audience. And I’m saying, bigger is fine. But there’s another alternative. And it does cost something in terms of the energy you need to put into the fans, but it’s another possibility. So I still think it’s a valid alternative way and has been proven now many, many, many, many times, particularly on the YouTube dimension. So the math still works.

The idea of the Thousand True Fans for those who are listening and not understanding is that if you are a creator of any type, using technology you can have a direct contact relationship with your audience, meaning that you have their emails or phone numbers and they can contact you. If you can have direct contact, so they pay you directly, then you don’t need millions of fans to be supported. You could have as few as a thousand true fans, true fans being someone who will buy whatever you produce. They’re the true super fan who is going to go all in with you. And if you get a thousand of them and you could generate a hundred dollars a year from each of them, then a hundred thousand dollars, you can make a living. You’re not going to make a fortune. You can make a living. If you’re a duet, a duel, you have to multiply it by more numbers to make it work.

That’s the mathematics of it. But it also means that the most harebrained, craziest, weirdest idea in the world, the most esoteric passion that you have is probably with eight billion people, probably shared by at least a thousand people, if it was a one in a million. The difficulty is in making that connection. Well, how do they hear about you? How do you find them? And that’s the technology that we don’t have yet. The AI might be able to solve it. We might be able to use AI to make this matchmaking function that looks around everybody and says, you two are going to get along. This guy and you are talking about exactly the same thing. Have the same interest. Here, here are your thousand true fans.

I think it’s possible that we could imagine AI getting to the point of being able to do that kind of matchmaking. And that will again be another lift for the Thousand True Fans enabling the one in a million idea that you have with the thousand true fans that you need to make it work.

AD: What if, I think I feel this way, you have a lot of fans, but they don’t want to pay for your stuff? Are they not true fans?

KK: They’re not true fans. You have the true fans and you have the avid fans and you have casual fans. And by the way, the true fans become the best marketers for your other fans. The whole thing about the thousand true fans is that’s not all your fans you have. You have lots of other fans. But yeah, you need the true fans. That’s about whether you’re useful, beautiful, true. Just because you’re creative doesn’t mean you’re going to have a thousand true fans. You have to be used, you have to be wanted, all those things. If you are intending to make a living out of it, then you have to be appealing to other people. That’s very, very simple. This is not like UBI where we’re going to support you no matter what. There’s a marketplace here. And if you want to be supported, you have to be producing things that people find valuable enough to pay for.

There’s a separate challenge of how you balance that trade-off of serving your fans versus your own inclinations. And that’s the classic Bob Dylan going electric. They want to hear the same old thing, which is what they want to buy, he wants to go in a different direction. And you kind of have to educate them. That’s a whole other challenge. But the point here is that if you can solve that challenge, it’s much more doable than having to have a million people pay you. So it doesn’t change the challenge of getting people to pay you. It’s just saying, you don’t need a million people willing to open up their pockets.

AD: Do you feel like you wrestle with that challenge? Or do you feel like people are kind, you’ve got your thousand and you’re good?

KK: I’ve been lucky in the sense that oftentimes when I’m interested in something, it turns out that other people are as well and are willing to pay enough to do it. But I’m not reliant only on the thousand true fans. That’s what I’m trying to say. I’ve had publishers and I’ve had a magazine. And so, while I have a thousand true fans, I’m not reliant on them fully. So I have a little bit more leeway. And that’s part of the evolution. The Thousand True Fans is only one option. And there are other avenues and sometimes it’s the place you start. I’ve been doing this long enough that I have more than just a thousand true fans.

AD: If you were starting out now though, given everything is the way it is, how would you do it? How would you make Wired? Would you make something like that?

KK: It’s a good question. I don’t know. Starting a magazine these days would be really tough, because we’re in this period of time when it doesn’t make any economic sense to have a magazine. The only magazines that are working are subsidized fully. But we’re in this period where it’s almost going to be feasible. Substack is kind of showing the way. And then I think the next step after that is to have full-blown magazines where you have multiple authors and people are kind of trained again, re-educated to pay for good stuff. For a while, it was not the culture to pay. And Substack has really been leading the way of retraining people to be willing to pay for writing and periodic writing. And so I think the next step is an evolution of these multi-author things, which are all magazines. I don’t think it’s quite there yet. So if I was starting again, it’d be a little rocky to do it. You might have to have funding from somebody who’s willing to fund something to get it going until maybe a couple more years until there’s more of a base. So maybe that’s what I would do. Find somewhere that’s willing to fund and invest into something a little bit longer term.

What else would I be doing? Well, it’s very clear. I would be much more active on YouTube. YouTube is completely underrated, both in terms of its consequences and audiences.

AD: Say more about why you think that? Are you using YouTube a lot?

KK: Oh yeah, yeah. I’ve subscribed to like 400 channels. I watch way too much of it. Moving images is where the center of the culture is. It’s not books. It’s moving images. I have a little media empire, right? We do podcasts, newsletters, websites, books, everything, cool tools, all this stuff. The only place where there’s a growing audience is YouTube.

AD: That’s fascinating.

KK: Yeah, and it’s not really recognized. I’m sure school age kids learn more on YouTube than they do at school. And it’s subterranean in the sense that, in the old days, you would look at the newsstands and you would say, my gosh, there’s a lot of magazines for guns or there’s a lot of interior decorating and makeover magazines. On YouTube, you don’t have that sense. You don’t know that there are these huge, huge communities and whole domains of stuff that you don’t see at all. And it’s so much bigger and deeper than anybody realizes. People pay attention and now they’re doing merch and finding all kinds of other ways to monetize it. Again, the thing about YouTube is you don’t have their emails. So you have to do something else to move them into your thousand true fan domain because you can have millions of fans, but they’re not true fans in the sense that they’re not paying you directly. And so moving them into that true fan thing is another whole process.

AD: What do you think people will be paying for more, given the fact that AI can make really good quality work?

KK: Yeah. Well, I was just saying this the other day, am I paying for anything that’s completely generated? And the answer is no. I’m not. I’m not subscribing to any Substack that I feel is AI generated. I’m sure I’m reading things that are, but I’m not paying for them.

It’s unclear to me how far completely AI generated content of any type will go. On my Instagram, I do follow some AI artists, which I really enjoy, Time Traveller, and there’s Joann. There’s a bunch of them that I love and it’s only AI generated stuff. I haven’t quite got to whether I would pay for them or not. The reason why they’re so good is because there’s a lot of them in it. It’s not just pushing the button kind of thing. It’s a skill. And I think what we have learned so far is that there is a whole bunch of art that I want to make that I could not generate because there were no words for it. That art was always tethered to language. I was trying to make the thing where there is simply no language for it. Even if later on when you could do the reverse prompting and take a prompt out of it, I was still not going to produce what I wanted.

So I think there are still constraints within these models and what they can produce because of what they’ve been trained on. And that’s going to continue for a while, even though we are trying to make them broader and give them some abilities to explore areas. They’re still constrained by what has been produced. Therefore, I think while there are lots of things that can be done that are really going to be fantastic in that space, there’s a lot that they aren’t going to be able to reach for the time being. And so the human alone or human with AI is still going to be a very, very profound source.

In the near term, 10 years, 20 years, I see lots of partnerships with AI as creative. I’m using this thing, a beta version of Google, I call it a writer’s room. It’s like every creative writer could have a writer’s room. We have multiple writers working with you on your project. And I can see more of that. There could be something that’s completely AI generated. And I think that it’ll be less interesting than the one that’s co-generated. And then there are those who won’t use it at all. So I see those two: those who don’t use it at all, and co-generation. But 100% generation, I don’t see that being that interesting to most people. It’ll be out there and there’ll be some uses for it. But for art, not so much. For everyday logo generation, yeah, great. There are different levels of what we demand of creativity. In some cases we don’t demand very much and it’s going to be sufficient.

AD: I feel like the appreciation of that kind of weird AI art will be similar to how people appreciate Gonzo, Outsider because it’s bad.

KK: Yeah. The constraints and limitations of any media later on become that kind of defining character that people are nostalgic for. You can see that in Midjourney already. Some of the early Midjourney stuff is so Midjourney-ish. That will be like a style at some point. So, yeah, I think you’re right. It would be kind of an edgy thing where you have this alien art, but a lot of co-generated art that’s really, really good, and then some human only. More choices.

AD: You strike me as a very chill guy. Are there things that stress you out? What gets you really?

KK: No. I’m never stressed. Why should I get stressed? It’s not good for you.

AD: I didn’t know that was possible. How do you do that? Or have you always done that?

KK: I’ve always done that. I must be a genius. No, but I also engineered my life not to have stress. I married someone with no drama. It was very deliberate. No drama. What you see is what you get. There’s no games, no hidden secrets, that kind of stuff.

AD: What advice would you have for very stressed out people then?

KK: I think you’re asking the wrong person. I have no idea. You should ask someone who’s very stressed. They’ll have answers for you.

AD: I want to know what you said you designed your life around.

KK: I think taking a long view, as much as possible. This too shall pass. The thing about the long view is the little tiny ups and downs. You realize that’s just going to be overwhelming over time. Understanding that setbacks are temporary. That’s the optimistic view. Setbacks are not about you, they’re not you, they’re just temporary things that can be overcome and will be overcome. So when things are happening that I’m not happy about, it’s like, well, okay, we’ll get around this. So what’s the best way to deal with it rather than getting upset over something?

Here’s one thing that I, even as a teenager, realized: when people are really angry or rude or whatever, I just imagined that they have a disease. It’s like, this is a symptom of an illness. And so it turns to sympathy rather than anger. It’s like, I’m sorry that you have that thing that makes you so angry. That must be terrible. So rather than responding with anger, I say, they’re sick. They have an ailment. I try to be polite, which is also disarming. So yeah, on the road when someone cuts you off, I try to think, you’re having a bad day. I’m sorry you have to do that.

AD: Wow. Do you meditate?

KK: No. I don’t feel any different afterwards. It’s the same. I have a natural high, I guess. Never did take any drugs. Never take any. I don’t think I can teach anybody any of this. I do have a book of advice.

AD: Yeah, is there anything you’d add to that?

KK: Yes. When you’re doing heavy manual labor, a change in position is almost as good as a rest. If you’re writing, you want to be as specific as possible. Instead of saying there’s a flower in the vase, you say a pale rose rests on the lip of a water glass. The more specific and concrete you can get, the better your writing will be. Some investing advice, which is don’t buy stock unless you’re willing to hold it for three years. That’s investing rather than just day trading. And that will generally pay off better for you.

I think I also recommend for long-term happiness that you try to do something useless every day, like drawing or art. I make art. I have this huge book and I needed a book stand. So I made this book stand out of scrap wood. It’s really, really weird, but it looks kind of beautiful and funky. There’s a certain funky style that I like of unfinished rough stuff. Anyway, I spent a lot of time on it. It’s completely useless in that sense, but it’s beautiful. It just brings me all kinds of pleasure. So yeah, try to do something useless.

You know, a lot of people talk about trying to optimize their life and they’re doing the minimize things, get through stuff as fast as possible. And I think you want to do the opposite. You want to try to work on things where you want to spend as much time doing it as possible. So you want to look for those things that you want to keep and never stop doing. That’s the sign of success. It’s not how little time you work on things, but how much time you work on things. And so try to steer your life towards the things that you just want to spend as much time doing as possible, whatever that may be. Like talking on a podcast with interesting people, do more of it.

AD: I know you have a new book out. I want to talk about that. Tell us. Bam!

KK: Yeah. So here’s cool and useless. I have this book, Colors of Asia, which was based on about 300,000 images that I took in Asia over 50 years. And the weird whimsical thing is that they’re all arranged by color. So I have pages of these sort of odd, remote, esoteric stuff that I saw over 50 years in remote parts of Asia. And now they’re all arranged by color. And if you like really esoteric things, this is a book for you. It’s for designers and people who like alternative ways to design.

So it’s Colors of Asia. And I have a Shopify where it’s a self-published book. And I only printed a thousand for my thousand true fans. So if you’re a fan, there is a copy for you. Nobody was yelling for this. No one’s saying we need this book. Nobody said that what the world needs is a book of photographs organized by color. I just decided it just tickled me and I haven’t had as much fun making a book in a long time. I just really had fun doing it and hopefully some of that enthusiasm and smiles came across. And so it’s art. You don’t need to read this book! It is cool and useless.

AD: Yes, we need more of that. I love the: nobody asked for this, but here it is.

KK: Nobody asked for it. And by the way, some of these photographs are from the 70s, 80s. Even stuff from the 2000s is not happening anymore. Like the elephant processions in India, animal rights legitimately are concerned. Like, no, they shouldn’t be in processions, elephants. So they’re gone. And so this is also a little time machine of seeing things that used to be, but they can be inspirations for things that could be now.

AD: Well, thank you. I want to close with a quick speed round. First question, how would you describe your relationship with AI?

KK: For me it’s an intern. A useful intern.

AD: What do you wish AI could do but fear that it never will?

KK: I don’t see anything it can’t eventually do.

AD: Everyone’s making predictions about AI. Let’s make a prediction about humans. In 10 years, where will humans be?

KK: Ten years will be just about where we are right now. I don’t see much change in humankind in that short period of time.

AD: How about a hundred years?

KK: A hundred years, we might begin to speciate in terms of there might be people who want to edit their genes and others who will never do that. So I could see some genetic diversion in 100 years.

AD: What question about AI and creativity isn’t being asked enough?

KK: I suspect that we’re going to have multiple kinds of AI. So I don’t think we talk enough about the plurality of AIs and the ways that they’ll be different. And there could even be AIs that are developed and acquired and programmed just to help artists with different biases and different backgrounds. So I think we don’t talk enough about the plurality of AIs.

AD: Last question, what do you wish people talked about more instead of AI?

KK: I think there should be more art in the world. I think there should be more art in corporations. I think artists in residence have proven to be powerful within corporations. I think artists should be more comfortable in their role. And again, what they’re doing is often useless and that’s hard to justify in a corporation. But we know that actually they will be productive in an inadvertent way. They’re inadvertently productive. It’s not a big sell, but it is true. And it does work. So even though they’re doing useless stuff, in the end, it’ll be more productive. That’s kind of a weird thing. But yes, that’s what we need.

AD: Cool. That’s a great place to end. Thank you so much. This was amazing.

KK: Thank you. I love your questions. Best to you and don’t stress. It’s not good for you.

This project has been a labor of love (emphasis on labor!). If you’ve enjoyed these conversations, send us a signal so we know you want us to keep making them.

Before we wrap the series, there’s a bonus 11th guest coming next week: (!!!)

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A conversation with Oliver Burkeman

Oliver is the author of Four Thousand Weeks. He formerly wrote the weekly column This Column Will Change Your Life for The Guardian. His farewell piece is a must read.

It took many many emails to schedule this conversation, which I interpret as a mark of integrity. Oliver has spent years saying that the pursuit of “getting on top of everything” is a doomed project. The man lives by his philosophy.

His vibe reminded me of a quote I love: “You are not paid to be on top of things. You are paid to be in the bottom of them.”

In this conversation, he talks about why he believes creative work gets its meaning from the time and attention a human puts into it, what it means to make things that feel alive, and how he is planning to stay human in a world tilting toward soulless automation.

I loved this one.
Enjoy ;)

Or listen on Spotify and Apple Podcasts.

(Best if you want to highlight your fave moments with Podcast Magic).

The edited transcript

Alex Dobrenko: What I understand your vibe on AI to be, and you can tell me if I’m right or wrong, is you seem to have a “this isn’t great, it’s not for me” stance and you’re a little annoyed that other people are talking about it all the time. Is that how you would characterize it?

Oliver Burkeman: You’re tapping into an accurate, all-purpose curmudgeon aspect of my personality that I don’t disavow. I’ve been through various phases of viewpoints. There was a brief time when I felt convinced by the science fiction doomer arguments about AI and the instantaneous eradication of humanity, but that was a little earlier, prior to the recent ChatGPT releases.

Now, I find myself thinking... at the most extreme end, I feel like I’m sometimes going crazy because it seems so clear to me that certain ways people are thinking about LLMs and integrating them into their lives are not honest or authentic. The thing that specifically bothers me is people’s readiness to believe or proceed as if there’s a consciousness there.

And when it comes to the creator economy, I have a growing sense that there could be an important reason not to use these tools too much. The goal is to retain a kind of raison d’être in an economic sense, to have a competitive edge. There could be a real benefit to doubling down on the purely human instead of allowing oneself to be shaped by these tools.

I’m not a total Luddite. I should say that at the same time, I’m not coming from the perspective that this has no merit, or that there won’t be great innovations in certain corners of scientific research that are really transformed by it.

AD: One thing I clocked early on about all this AI stuff is the language around it. When we talk about Google, we say, “I Googled something.” I’m the one doing the Googling. But with ChatGPT, we say, “ChatGPT did it.” We gave it agency pretty quickly. I think that’s really hard to claw back. Most people don’t even realize they’re giving it soul. Why do you think that bothers you specifically?

OB: What I’m about to say may cause people to completely dismiss me, but I have been uneasy about something similar all the way back to the advent of Alexa and smart speakers. I’m the kind of person who always claims I’m not going to adopt a new technology, and then I do, like everybody else. But the voice-activated stuff is an exception to that rule. We don’t have it in our house, and I’ve always felt there’s something creepy about a technology that invites me to treat it as if there’s a person there, while at the same time existing to obey my every command.

We recognize that while the primary reason that slavery is a moral abomination is what it does to the people who are enslaved, there is something deeply corrupting about being someone who treats someone else as property. I’m not saying it’s the same thing as slavery, but there’s a depravity in treating a person as nothing but a means to your end. And although it’s obviously not the same thing when it’s just Alexa, there’s a certain orientation that you have in your interactions. Years ago, people were noticing that Alexa turned their kids into jerks because it trained them to bark commands. They had to be reminded they were allowed to bark commands at that lady in the box, but they weren’t allowed to bark commands at their mom or dad. I don’t think anything good comes from convincing oneself that there’s a person where there isn’t. It probably damages one’s relationships with real people.

AD: Do you use it at all?

OB: I suspect all of us are using it in ways we can’t control, with it being behind other services and platforms we’re using. Other than that, I saw somebody classify how the different generations interact with AI, and it said that for Gen X, it’s a slightly glorified search engine. I’m pure Gen X in that regard. I use Perplexity because it’s way better than Google for finding links to existing sources. It seems kind of dumb on some level to refuse to do that.

One of the things that raises my hackles is the claim that the only reason not to be in awe of these technologies is that you haven’t used them enough. It’s certainly true that people who use ChatGPT a lot come to think it’s great, but I’m not sure whether that’s because they’re discovering its extraordinary depths or because they’re sort of mesmerizing themselves into the understanding that that is the way to work.

And I’m not saying this won’t change at all. I’m not putting a stake in the ground to say I will never extend my use of these tools in the research phases of writing, but it seems totally clear to me that I don’t want to use it to create first drafts of things I’m writing, because first drafts are not just kind of amateurish stabs at things. They are where the concepts are connecting or the structure of the piece is being imperfectly built. And I don’t want to use it for later stages where my voice, which is all I’ve got as a writer, is put in.

I’m open to the possibility that I’m just an out-of-touch old man, but the conscious engagement with those processes is the point. Every way in which one could skip those steps would seem to me to reduce the meaning and value of the process.

AD: Do you care if other people do it?

OB: When I read a piece of writing, I think it’s critical to the value of that experience that I’m reading words that emerge from a person’s own conscious, emoting, and thinking sensibility. It’s not just that the points made are good ones or that the writing is stylish. It’s the fact that it came from another consciousness a bit like mine. It’s an instance of a relationship.

There was this back and forth between AI skeptics and promoters, which hung on whether AI could ever write a novel to the same standard as a human novelist. Some people said it could never happen. My argument was always not that an LLM couldn’t create something of equal merit, but that the fact that a novel was written by Jane Austen is a big part of what gives it its value. It’s not just about the end result; it’s about where the end result comes from.

I think I do care that the people I’m reading aren’t heavily relying on LLMs. Someone will say, “You can’t tell, and I’m sure you’ve already been tricked many times.” Absolutely, don’t deny that at all. The point I’m making is that when I do find out, something shifts in my experience of the product completely. If we had an interesting conversation, and you felt it was a useful use of your time, but then you discovered you’d been interacting with a simulation, something really important would be sapped from that experience because it turned out there wasn’t a person there.

AD: You would have felt lied to. I think people don’t like that feeling of being tricked.

OB: Exactly. And I think it’s a deep point because it exists on that very obvious level of lying, but there’s also a subtler level. Almost any kind of writing that comes from a perspective that implies that the author has thoughts, feelings, and opinions is already implying that it’s human-created, even if you were technically honest about it being an AI. What are we doing here if the very act of telling me what you think is an assertion that you are a conscious sensibility, but you’re not?

Now there are types of writing that this doesn’t apply to, right? I mean, I think it’s clear that I don’t care if the instruction manual for my new dishwasher or something has been created in that way. I think we’ve got to be honest about that.

AD: In an earlier interview, the writer David Perell brought up that there are two types of writing: informational, where the reader is in the driver’s seat, and the ride-along style, like Joan Didion, where you get to come on the author’s journey. What do you think about that?

OB: I think he’s right about the distinction, but I don’t know how big the set of things where there being no human involved isn’t a problem really is. The technical writing for how to use an appliance feels like one extreme just because we’re probably already so accustomed to poor quality in that regard. Though now I’m starting to think it would be fantastic to have beautifully authored dishwasher instructions.

AD: I was just gonna say that Joan Didion writing how to use your dishwasher would be incredible.

OB: Exactly. Even if that’s silly and not going to happen, that incredibleness tells you something.

One thing that people have said is that those of us who want to either produce and sell or consume human writing are going to be engaged in a sort of premium artisanal sector for whatever proportion of the population hasn’t had their jobs taken away by AI and can afford to buy such things. And I think there might be some truth to that. Maybe most people don’t think like me and they’ll settle for something that I turn my nose up at and that’s because I’m a snob in some sense. But I do think there’s something substantive here, right? It’s not just a nostalgic commitment to the human for the sake of it. There’s something very, very real about the importance of there being a human author.

I wrote two books on the finitude of human life and how the fact that we have the sort of finite time is a terrifying thing, but also gives value to what we do. There is something important there too, right? If you’re going to pay for a copy of a book, there’s something important about the fact that I used up a bunch of my time to create that. And I gave that time to that when I could have given it to something else. And I thereby created some kind of value that I’ve got the temerity to ask you to pay for. And this all takes place within the world of human limitation where scarcity generates value. Something’s gone wrong with that if it actually took me none of my valuable time at all. Because then what’s going on in that transaction and why should you pay?

AD: Right. I mean already all of this is kind of true in that there’s all those apps that summarize a book for you in 10 minutes. And nobody likes that stuff. That stuff sucks. I find a lot of solace in the idea that people can just tell when something is bad.

OB: People can just tell. But even if we get to a point where people can’t just tell, it’s like... if I’m right that it matters that something is created by a human emoting consciousness, then why would that be changed by the fact that the simulation is so good that I can’t tell the difference?

AD: One of the writers I interviewed, Venkatesh Rao, is very pro-AI. He uses it in his writing and said that soon he’ll just combine his AI-generated content with his other writing. He had this take that the idea of an individual being responsible for a piece of work is fairly recent—a blip in history. Before that, artists didn’t feel they were the ones who produced something; they were the vessel for God or a linguistic commons. He suggests AI is a return to that. What do you make of that?

OB: I would sort of turn the tables and say it’s exactly that kind of idiosyncratic thought that has made me value the writing that I’ve come across from him. So it’s like, put that in your pipe and smoke it. I’d need some time to think about this, and I’m sure that’s an accurate account of history, but I would suggest that there’s the modern idea of the individual writer as a genius, and then there’s the idea that this person is channeling something from beyond their simple egoic consciousness, like the collective unconscious. These two things seem to be different ways of talking about the same thing.

However, the kind of role of aggregate and generic writing that seems to be at the core of how LLMs work seems to be a separate thing. It’s one thing for a writer to express tales that have been in the culture forever that have moved through them, and something else entirely to take a whole collection of individuals’ work and train large language models on it to produce outputs. As I understand it, there’s something tending toward the generic, the most averaging-out of perspectives. Generic is not the same as collective necessarily.

AD: I think I get what you’re saying. I also got what he was saying. I find that whoever I’m talking to, I’m kind of convinced they’re right. But I find myself asking: Do I actually feel good when I’m using AI for creative work? For me, the answer is not really. I don’t feel very creative.

OB: That feeling in and of itself is why we do these things, right? On some level, we spend large parts of our lives doing this stuff in order to feel good about it. Not that you’re going to be cheery and happy at every single stage of the creative process, no one I know anyway, but that, if you don’t feel good about it persistently, then that’s its own message.

AD: I don’t expect to feel cheery and happy. I actually expect the opposite. And then I expect to get to the other side of that for a little bit. But with LLMs, it kind of just cuts out that part where it’s a mess and I hate myself but that’s half the thing for me is to get to the other side, right?

OB: That’s a really good way of putting it. When you say it doesn’t feel good to use AI, you’re not saying that when you’re not using AI the process is always pleasant. What you’re feeling is something like an authentic engagement with reality. You’re in life. That can absolutely be a very unpleasant experience, but it’s an alive experience.

Maybe what we’re coming to here is some sort of consensus conclusion that the important thing is to have a clear-eyed sense of what you find meaningful and not outsource precisely the bit that gave it the meaning, which is something we’re prone to do in lots of areas of life. Maybe there are people for whom the meaning isn’t the process of consciously bringing ideas into connection with each other. I struggle to see what the meaning is if it isn’t that, but maybe there are other parts of the overall process that are fulfilling.

AD: For the reasons you write about: “I have to save time, and I have to make money.”

OB: Clearly, that’s what’s driving a lot of it. The sense that you have to do this or you’ll get left behind. I have a hunch that it might be the other way around: that my best chance of continuing to make a living doing this thing that I find meaningful is to not join the race to do what everyone else is doing, thereby making myself the same as everyone else and not worth buying the books from because what’s the difference?

AD: What’s your advice for writers and creatives who are worried about not fully using AI?

OB: If you have a clear perspective you want to communicate, give yourself a chance to see if it resonates with people before you give up. I would definitely encourage anyone who feels a sense of dissonance between what they’re being asked to do and what they think they truly bring to the world, to focus on what they really bring to the world. I think that people are going to continue and ever more vigorously respond positively to the sort of marks of the signs of the human. The very best way to do that is just to be a human doing it rather than try desperately to create prompts for LLMs.

AD: Yeah, I think a lot of great art that’s going to come out is going to be about that dissonance between what you feel like the economy wants you to do and what you want to do.

OB: Absolutely. And I’ve always felt on this issue of, “how much do you compromise what you want to be doing in order to make it financially viable?”, there will always be people who suggest that the answer is, you compromise everything, right? You just jump on the bandwagon and go with the herd. But there’s a certain point in that process where you might as well retrain as a plumber. Why insist on continuing to travel under the banner of “I’m a writer” if you’re not doing any of the things involved in it? If you’re going to go that far, then maybe that’s just not the thing for you to be doing that would bring you alive in life.

AD: I’m curious how you are actually using AI in your creative process, if at all?

OB: Basically the only thing I use is Perplexity to generate lists of other sources, pretty much all of which are written by individual human beings. I am drawn to the way that Perplexity footnotes and links the sources in its output. Honestly, it feels like I’m just using it because of the famous decline in the quality of Google’s search in the last few years. Honestly speaking, that’s where I’m at with it. Maybe this will just seem completely absurd in a few years time to everybody, even to me. I still think that’s probably a price worth paying for continuing to find the experience of writing as meaningful, albeit infuriating and maddening, as I currently do.

AD: How would you describe your relationship with AI?

OB: I don’t think in relationship terms. When it comes to AI, I don’t think you only have to have relationships with living beings, right? I feel like you can have a relationship with a landscape or a place. So it’s not like the word is completely inapplicable, but no, I try quite hard to keep it the kind of relationship that I have with my MacBook or the pens I use. It’s a tool and I don’t want to forget that.

AD: What do you wish AI could do, but fear that it never will?

OB: Again, I’m not sure that I want it to do anything that it doesn’t yet do. Obviously, if there are specialist domains where it can cure cancer, I’m not going to be sitting here saying, don’t do that, because I’m not completely insane. But I start from a place that makes me not want to answer that question, I guess.

AD: Everyone is making predictions about AI. Let’s make a prediction about humans. Where do you think humans will be in 10 years?

OB: The best gamble you can make about how we’ll be in 10 years is how we are now. I think we will be messy, at each other’s throats, boundlessly creative, and constantly on the verge of destroying ourselves—but not actually doing so.

AD: What question about AI and creativity isn’t being asked enough?

OB: I don’t know how to phrase this, but it is that question of how much of the value of creativity is connected to the sentient, emoting, thinking awareness of the creator. We talk about whether AI is or could be conscious and what that would mean, but I think we could do with talking a bit more about how human creators are conscious and why that matters so much to what they produce.

AD: Cool. And last question, what do you wish people talked about more instead of AI?

OB: Almost anything.

AD: Haha. Are you working on anything new? Anything we can sneak peek to people?

OB: I am working on a new book. It’s very hard to exactly say what it’s about at this point. I’m not being coy. I’m just struggling for the language. But it is something closely connected to this idea of aliveness or what it is that gives human life that feeling of being worth living. AI is definitely implicated in this discussion, although I’m not going to write a book on AI because there are enough of those.

AD: I can’t wait to read it. This was awesome. Thank you.

OB: It’s a pleasure. Thanks for your enormous patience in setting this up. I’ve appreciated that.

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A conversation with Billy Oppenheimer

I first stumbled upon Billy through an essay he wrote about the cup of coffee theory of AI, then fell down the rabbit hole of his notecard system (the paper cousin to what we’re building with Sublime). His Sunday newsletter is one of my favorites. When we finally got on the phone, what I loved most was his pace. Unrushed. He’s just doing the work, while the rest of us sprint in place.

In this conversations, he covers:

• Why taste is still the most mysterious part of creativity.

• Why he believes the people who get the most out of AI need it the least.

• The process behind his research work for Rick Rubin and Ryan Holiday.

• The edge that comes from doing the slow, tedious work of expanding your knowledge.

• His prediction for where humans will be in ten years.

• Plus, a few book recommendations

This conversation is part of Whoa: Vol II: Conversations on AI x Creativity. If you’d rather savor instead of scroll + want access to all ten conversations, grab the physical + digital zine.

Or listen on Spotify and Apple.

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The edited transcript

Alex Dobrenko: I read your cup of coffee theory on AI essay from 2023, which feels like an eternity ago in AI time. Has your thinking changed since then?

Billy Oppenheimer: I stand by most of what I wrote in that piece. My main point was that AI is just another tool, and creatives have always had many different tools at their disposal. The foundation of making stuff and having it land with an audience is taste. I think AI has maybe gotten better at taste and discernment, but it’s still an impossible question to answer.

Every creator has made something they thought was the greatest thing they’ve ever done, put it out there, and it was crickets. Conversely, something you’re on the fence about goes crazy. It’s an impossible thing to unlock with any certainty. The tools can help you, but at the end of the day, it’s always a gamble. As fast as AI moves, people’s taste and what’s popular are also moving all the time. I don’t think a tool can ever give you certainty around that.

AD: When you say it’s gotten better at taste, what makes you feel that way?

BO: In that piece, I used an example of asking it for quotes. Because of my work with Ryan Holiday on The Daily Stoic, I’m constantly engaging with Meditations by Marcus Aurelius. At the time I wrote that piece, the quotes were not only not in the realm of the topic I was looking for, but they were also made up. Now, the quotes are more legitimate. It might say, “The quote you’re looking for is book seven, passage four,” and then I go to book seven, passage four, and that’s not the quote. So I still have to verify everything. It’s a “trust but verify” situation.

I’d love for it to get to a place where I can give it a fragment of a quote from Meditations and it can just tell me exactly where it is. It’s actually one of my frustrations as a reader. I’m seeing a lot of “loosey-goosey-ness” in a lot of writing, like, “As Mark Twain said...” Then I’ll check, and it’s usually not something he said. I think that’s happening because people are asking AI, “Hey, I’m writing about this topic, can you give me quotes from credible people to legitimize it?”

AD: I remember the first time that happened to me. I was writing something and wanted a movie quote to say something in a funny way. It gave me the perfect quote from The Sandlot. Then I looked it up and realized it was never said. And it’s not that it’s lying; it just doesn’t know that truth is a thing. It was a real rude awakening.

BO: Yeah, and the certainty with which it gives you those quotes...

AD: I’m fascinated by your process as a research assistant to Ryan Holiday and Rick Rubin. What is your research process?

BO: My process is that I’m constantly reading, listening, and watching things. I do all my reading with physical books, so I have a pen in hand and I’m making notes in the margins. Once I finish a book, I put it aside for a bit and then go back through it with the note cards. Anything that holds up as interesting or potentially useful I write on a card. A lot of times, on an initial read, I might mark 100 pages in a 300-page book. When I go back through it two weeks later, the number of things that remain interesting are a fraction of that. I like letting time filter things out. When I go back a second time, it’s a test: “Do I want to take the time and effort to transfer this onto a note card?” If I can’t muster the willpower, it must not be as interesting as I thought.

I make cards and put them in various boxes. When a section piles up to like eight or 12 cards, that’s my signal that there’s something here. Let me see if I can piece these together.

Sometimes I’ll note in the margin to ask ChatGPT if there’s something I didn’t understand. For example, I’m reading a collection of letters by Louisa May Alcott, who is writing in the 1800s. She’s using some phrasing that doesn’t make sense to me. I’ll ask ChatGPT, “What does this mean?” but as far as capturing or finding material, all of that happens in the reading of books.

AD: You don’t use it to make crazy connections between things. It sounds like you prefer whatever naturally connects in your brain more than what AI would do.

BO: Yeah, that’s my favorite moment as a reader— being like, “This is just like that other thing I read in that other book that seemingly doesn’t belong together.” So I wouldn’t want to outsource that part of it. The times I’ve tried to ask AI things like, “Hey, I’ve just learned about this story. Can you think of any other historical examples with a similar story?” it’s always the same handful of characters, like Oprah and Steve Jobs. I want examples that are not in ChatGPT’s knowledge base.

AD: That’s a great point. What creative fears or insecurities does AI surface for you? Are you worried that it’s going to replace you in research?

BO: I think there’s always going to be a need for human filtering. Even if AI gets really good at generating a first draft, you’re still going to need a human to do some final touches or to integrate it. I can’t see a time where AI is doing 100% of the creating. Maybe that would just be a genre.

I’ve also seen in the office with Ryan — he has a bookstore in Bastrop, Texas – and I go over there a couple of times a week. Sometimes he’s like, “Let’s mess around with AI. Let’s give it an article we published last week and ask it for feedback.” and what Ryan thinks to prompt it with gets better results than what I’m able to get. Because of the 20 years he’s been cultivating his ability in the craft of writing, what he thinks to do is just different from what I would think to do. I’ve seen the differences in what people get out of AI. The people who can get the best out of it need it the least.

I feel like how you cultivate yourself as a person to get better and better results out of these tools is not something we talk about enough. My concern is that if you’re somebody who’s just coming out of college and wants to pursue a creative profession, and you go straight to these tools, you’re not going to do the work to cultivate those things.

I think there’s an edge to be had in doing the tedious work of expanding your knowledge base around a subject.

AD: What would you say your personal AI thesis is? The core belief that drives your decisions about these tools?

BO: I don’t know. I guess I don’t have one.

AD: Or maybe the fact that you don’t have one is itself a thesis. What advice would you give to people starting out who want to do what you do and are worried about all this?

BO: My advice would be to cultivate some skill set or knowledge and to do things that other people aren’t doing. I think I have an edge because I enjoy reading a lot, and people are not doing this amount of reading and finding these stories or ideas that the tools can’t generate.

I recently read a paper by a sociologist named Daniel Chambliss. He spent about 10 years with swimmers at every level of ability, from Olympic teams to high school and country club swimmers. He was observing what the Olympians do differently. His core point was that excellence is not a quantitative phenomenon, it’s a qualitative one. At the highest level, they don’t necessarily just train more; they do things differently.

He tells a story about high school and college coaches being invited to spend a week with the U.S. Olympic team, expecting to learn the secret to their success. Over the week, their enthusiasm drained as they realized the Olympic team wasn’t doing anything crazy different. It’s just the little things, like making your practice turn as if it were a meet. Those small things, over a year or five years, ultimately distinguish you from the people who aren’t doing them.

I love that phrase, “a qualitative phenomenon,” because it applies to many domains. It’s about figuring out what small, mundane, or tedious things I can do differently that will, over time, compound into a significant distinction. The paper was called The Mundanity of Excellence, and it’s a reminder that excellence often comes from focusing on those mundane things that many people either ignore or underestimate. For me, that’s reading books and putting in the effort to transfer that material onto note cards.

AD: The internet has a very fast pace, and what I notice is that your pace is much slower. Even in how you talk, and certainly in how you work and compile things, there’s a real emphasis on putting in the time. AI, on the other hand, seems to collapse time, promising you don’t need to spend any time at all.

BO: Yeah. I was just reading Make Something Wonderful, a book of Steve Jobs’s words. He was talking in 1983 about computers and said, “Let’s say I could move a hundred times faster than anyone in here. In the blink of your eye, I could run out there, grab a bouquet of fresh spring flowers, run back in here, and snap my fingers. You would all think I was a magician. And yet I would basically be doing a series of really simple instructions: running out there, grabbing some flowers, running back, snapping my fingers. But I could just do them so fast that you would think that there was something magical going on.”

It’s the exact same thing with a computer. We tend to think there’s something magical going on, but it’s just a series of simple instructions. I think that’s what a lot of people are attracted to about AI—it seems magical, but it’s really just the speed.

AD: When I use it, what I want is speed. I want a shortcut. You wrote something about “neck down.” It’s that feeling of, rather than just doing the thing, I’ll spend hours trying to create a weird little system that does it for me. AI is an accelerant of that desire.

BO: I literally have that note card right here: “neck down.” It comes from comedian Matt McCusker who was working a blue-collar job in a warehouse. His boss said, “Look, man, I just need you from the neck down today. I don’t want to hear any ideas. Pick the box up there and move it there.” I found that when I’m hoping AI can make a tedious task faster, it’s just a delay. I just need to sit down and do the thing. I’ll put that note where I can see it to remind myself, “For the next two hours, just go neck down on this.” It’s okay to do something I don’t necessarily want to do. And often, I’m glad I did it because in the process, I might stumble on something I didn’t know I was looking for.

AD: I’m curious to hear some of the specific ways you use it.

BO: Okay. This might be underwhelming, but I’ll give it a shot.

I use it when I’m reading and a phrase or metaphor is used that I don’t quite understand. For example, I was reading a journal by the French novelist Andre Gide, and he wrote about Kant’s dove. I didn’t know the reference, so I asked ChatGPT about it. It told me it comes from Kant’s Critique of Pure Reason. I was then able to find the passage where Kant writes about the dove, which helped me write a newsletter about it.

In the introduction to Critique of Pure Reason, Immanuel Kant writes about the seductive illusion of complete freedom, a life with no bounds. He compares the longing for unbounded autonomy to a dove cutting through the air, imagining that it could do even better in airless space.

This led me to Gide’s point that art is always the result of constraint. He wrote, “To believe that it rises higher as it becomes freer is to believe that what keeps a kite from rising is its string.” It’s a great illustration of how I get value from AI. If I had read that without AI, I probably would have just moved on. Now, I can use it as a tool to quickly understand references I’m unfamiliar with.

Another use case is when I find a cool framework or model and want to develop it further. I read a quote from Little Women about “head, heart, and hand.” I put it in ChatGPT and asked for real-life examples where this framework or these three different types of work show up. I was just going back and forth, exploring different angles, asking what some “head jobs” are—tasks that are strategic and forward-thinking. It helped me develop the idea more quickly.

This is similar to how Ryan and I work. When he’s drafting an article and can’t immediately think of examples for a point, he’ll put in an “insert,” and I’ll give him options. Now, I’ll go to ChatGPT and say, “Hey, what are some common, everyday situations where people meet circumstances that are not what they would have chosen? For example, your flight gets delayed.” It will quickly give me a list of 20, and I can pick the ones I like. This is a case where the speed of getting a ton of options is helpful.

I also use it as a kind of knowledge partner. I was reading an article that said, “Everything that LLMs say, true or false, comes from the same process of statistically reconstructing what words are likely in some contexts.” I realized I didn’t truly understand what statistics were, so I asked AI to help me understand it simply, in the context of LLMs. It then broke down how weather forecasting works, which is a great example of a statistical process. It collects tons of data and makes predictions based on historical patterns. Like there’s a 70 % chance of rain tomorrow because the last hundred times the weather and the atmosphere and the pressure, etc were like this, it rained 70 of those 100 times.

Now, when I think of LLMs, I can compare them to weather forecasting. This back-and-forth process of drilling deeper and following my curiosity is a great way to use the tool. I think I then asked, where does weather forecasting go wrong? There’s no embarrassment in asking basic questions, so it helps me go several levels deeper into a topic than I otherwise would have. Before these tools, if I saw that line and didn’t understand it, I would just think for a second, how could I go about understanding what that line means? And would probably be like, there seems to me no easy way to do it and just get on with the next thing.

The other thing I use it for is when I’m struggling with a sentence. I’ll say: Can you give me 20 variations of the sentence? and usually there’s not one that’s entirely perfect, but I like this word use here, this phrase here. And then I’ll put the sentence together myself. I could probably sit here for a long time and figure it out but that is a case where the speed of getting a ton of options is helpful.

AD: Do you ever feel like you’re cheating by using it?

BO: No, I don’t. The sentence you’re helping it edit is yours. It’s your idea. If you sent that sentence to ChatGPT and asked for help, and you also asked me to do the same thing, we’d both come up with different versions. Your taste and discernment ultimately decide what to use. You were the conductor. It’s like how Andre Agassi used a ghostwriter for his book Open, which is one of my favorites. It’s okay to have a collaborative partner. A screenwriter gets credit for a script, but I’m sure they had other people contribute or overheard lines they put in. Does that minimize their work? Now, if I just asked it to write a thousand-word piece and then posted it with no corrections, I’d probably feel weird about that.

AD: Everyone’s making predictions about AI. Let’s make a prediction about humans. Where do you think humans will be in 10 years?

BO: I think we’ll be focused more on how to become better humans to get more out of the tools. Instead of courses on how to be a master prompter, we’ll see more on how to become highly competent in a domain so you don’t have to rely on those courses.

AD: What question about AI and creativity isn’t being asked enough?

BO: Is it actually good, or is it just fast?

AD: What do you wish people talked more about instead of AI?

BO: Books, maybe?

AD: Do you have any book recommendations or recent things you’ve loved?

BO: I recently loved A Swim in a Pond in the Rain by George Saunders. And Consolations and Consolations 2 by David Whyte. The chapters in those are each a word, like “burnout” or “anxiety,” that he explores from a poetic perspective. I also love collections of letters and journals. If I get interested in a person, I’ll find a book like that. It’s a great way to hear their core stories in their own words.

AD: I love those too. All right man, this was amazing.

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A conversation with Anu Atluru

When we asked in the Sublime Slack who we should interview for this series, the most popular answer was: . She writes banger after banger after banger. Some of my favorite things she’s written are Make something heavy and Pursuits that can’t scale

In addition to her longform bangers, she can also craft an unfairly good sentence that leaves me thinking ugh, I wish I wrote that.

In this conversation, we cover:

• Why every human skill becomes either extinct, art, or sport.

• The psychological cost of creating on algorithmic platforms.

• Why the future belongs to people who are part media, part machine.

• Why our ability to detect “GPT-isms” gives hope for humanity.
  

  and more…
  

This conversation is part of Whoa: Vol II: Conversations on AI x Creativity. If you’d rather savor instead of scroll + want access to all ten conversations, grab the physical + digital zine.

Or listen on Spotify and Apple.

(Best if you want to highlight your fave moments with Podcast Magic).

The edited transcript

Alex Dobrenko: There’s a line of yours “I don’t want an AI, I want a teammate” that really hits hard. I’d love to start there. How did you get to that? What made you feel that?

Anu Atluru: For a few years, I’ve had this thesis that we are moving towards a world where people can do so much more by themselves. I wrote a piece a few years ago called “The Rise of the Silicon Valley Small Business” just before AI really took off. Since then, things have accelerated. The discourse around this is that previously, you might have needed a hundred people to create a company of a certain size. Now you might only need 20, or maybe even 10 or five.

In a world like that, my mind goes to, “How do you choose those 10 people?” One way is to choose people who are 10 times better than everyone else, who can produce 10 times more, and who will be 10 times more valuable to the business. The other way is to choose people based on whether you enjoy working with them, if they make you better, or if they help you express your voice, taste, or capabilities.

The question I keep returning to is: what do we actually want people for? In the past, we wanted them for labor, efficiency, and technical skills. Now, we want them for that, but we also want them for more interpersonal things. The test is: would I rather work with this person—or work alone with better tools? That will determine if they’ll be in my small crew. Which is a long-winded way of saying, even with all this tech, I still want a teammate.

AD: Yeah, it’s also a societal question of whether we, as people, will want to work with each other or with a tool.

AA: Right. I think in some cases, we’ll want to get out of the face of tools. We’ve seen this before, even before we called it AI, with the automation of call centers, customer support, and even self-checkout at the grocery store. In some of those cases, we’re okay not having a human there. In other cases, we want someone there. I have this framework in my mind that as we go forward on this automation / AI curve, every human skill will either become extinct, art, or sport.

Extinct when machines absorb it. Art when humans still do it because we care about the person, story, or meaning. Sport when we watch humans test their limits — often for its own sake.

We like to see what humans are capable of. We like to put ourselves in an arena and battle-test ourselves. Nobody will drive anymore out of necessity, but Formula 1 will stay popular. Computers beat us at chess, and yet we still love watching humans play.

What was once a necessary skill for production now becomes a skill in an arena that’s a sport or art. I think even building businesses is going to be more of an art or a sport than a necessity.

AD: The VC funding model feels like a sport. You’re betting on these horses, and it doesn’t matter if most fail as long as a couple are a huge success.

AA: Yeah, there’s a joke that venture capital might be one of the last jobs that won’t go away because it involves a sense of taste and the ability to pick and choose. I fundamentally agree. As long as humans are in control, we will still be choosing where to place bets, whether on entrepreneurs or Elon Musk’s expeditions to Mars or what have you. If we automate everything away, somebody still needs to make decisions about what we’re doing. In the end, when labor compresses, more of the job is judgment from the top of the pyramid.

AD: So talk a little about your background. You work in VC?

AA: I trained as a doctor, I now build products, invest in and advise startups, and I write – media, machines, and medicine are the three threads that run through my work. My writing ties these interests together. I don’t see them as separate worlds but as different arenas of the same question: how do people engage with them? Whether it’s a product or healthcare, I’m looking at what people want, how they use it, and what motivates them. What interests me most is what stays the same – because people are fundamentally the same even as circumstances change.

AD: I like that frame. It bucks the kind of exceptionalism that’s under a lot of AI talk, which is that this is different and will change everything in a way it never has before. What are the things we always do and how do you see them happening in the next five years?

AA: My bet is the next five years won’t feel as dramatic as the last three. We’ll absorb today’s breakthroughs, settle into plateaus, and then leap forward in sudden step-changes. New technology feels like magic, but we get calibrated to it in a week or two; it’s like we forget the revelation and it just becomes the base case. In ten years, much of life will look the same. We’ll still be ourselves, just with more leverage in our hands, and hopefully with health as the area of deepest progress. I’m not convinced progress keeps moving in an exponential or even straight line. More likely, it flattens and then jumps. I expect the biggest jumps will come in science and robotics—changes in the physical world.

I wrote a piece about the “gentle singularity”—the slower, more gradual shift than the ‘AGI’ moment we’ve been conditioned to expect. In this world, many jobs once considered knowledge work will look more like trades. Research becomes the opposing domain of new discoveries. Interpersonal skills rise in value because you can’t automate away human connection. This slower shift will tease out what is human versus what is machine. While AI gives us a lot of leverage, we still have to find purpose and meaning. I don’t think we’re all just going to be frolicking in meadows.

AD: It’s funny how revelatory the idea of IRL is. I have a friend who does online art workshops, and it blew her mind that she could just do one in her community, like where she lives. We truly have a certain subset of people who are just so used to everything being online.

AA: Exactly. It’s the Lindy effect. What was once will be again. Local communities and connections are where value was before the 25-year internet expansion phase. Everything went online, and we built big marketplaces that allowed for remote work. Now, we’re figuring out there are problems with that in terms of individual value versus the power law, and we’ll come back to what works for everyone, not just a few.

AD: I want to talk about your creative process and AI. How does it fit into your work? How are you using it?

AA: I’ve experimented with AI in every facet of my writing to understand it. I’ve found it’s most helpful in the upstream and downstream phases. Upstream, when I have an idea, I can use a tool like ChatGPT to offload some of the cognitive burden. Instead of just typing notes, I can have a back-and-forth conversation, pulling out the essence of a disjointed thought. This helps me distill an idea or sometimes realize it’s not that interesting. The risk is you get the dopamine of talking through an idea and then lose the drive to actually write. I wrote about this in a piece about how doom prompting is the new doom scrolling.

And then downstream, once I have a draft, I can use an AI tool like a helpful editor. I can ask it to review my work or even act like a specific person to get a critique. This is quite helpful, but like any feedback, you can’t take too many suggestions. You have to trust your own voice and gut.

AI is not great in the messy middle, where you are trying to figure things out. If I ask it to create a first draft, it will give me something, but it’s not me. The prompt would have to be too expansive to capture all the context and voice I have in my head. Starting from something that isn’t your own voice can derail the process, and you can end up iterating to nowhere.

For code and technical work, these tools are phenomenal: they open doors for non-technical folks and give engineers so much leverage. Verification still takes time, but because the work is functional rather than art, the assist is bigger — AI is most useful the closer a task sits to “functional” on that spectrum.

AD: It’s largely similar for me. I’ve tried things like, “Write something like Alex Dobrenko,” giving it notes and ideas. It’s a haunting experience because it’s not me. It almost feels like it’s making fun of me, using too many parentheticals. I try to get it to dial back, but then I’m editing some ghost of myself, iterating to nowhere. I find it helpful with editing, or in the beginning, like “Help me talk this through; ask me questions.”

AA: I get that feeling when I ask it to write something in my voice, or someone else’s, just to expand on an idea. It might put “it’s not X but Y” in every other sentence, or create endless lists. That gives me anxiety because it reminds me how mechanical the underlying thing is. I’m sometimes shocked that brilliant people are building these products, and they’re processing at a level far greater than many of ours, yet we can still so readily identify these “GPT-isms” – the new “tics” that arrive with every model update. The fact that we can do this within a day is fascinating and gives me hope that we have some time.

AD: It’s very sophisticated, but so are we. My background is in comedy and acting. You know when someone is lying in a scene versus when they truly feel it. I don’t know how to tell you why I know that, but I just know it.

AA: Right. It’s part of the human instinct to know what makes a relationship or response human. It’s not always predictable; it’s rife with biases, transference, and emotion. It’s a two-way street. People don’t always say yes; they push back and ask questions. This bidirectionality is what we instinctively suss out, and it often doesn’t exist in AI interactions. Until AI crosses that line where people can’t tell the difference, you’ll always feel like you’re controlling it, not engaging in a mutual situation, and human life depends on mutuality.

AA: It’s going to be interesting. Do you think much about education and young kids? I have a four-year-old and a one-year-old. I was showing my wife the GPT talk mode. My son overheard it and asked, “Who is that?” He then talked to it with such ease. It blew my mind because we have so much baggage about this stuff that he won’t have. It’s going to be really weird.

AA: That’s true. There’s a quote that says if a new technology emerges between your teenage years and 35, you adapt. If it emerges after 35, you think it’s horrible and can’t cope. On the other end of that spectrum are kids. This will just be a normal world for them. They’ll probably have tutors and friends that are chatbots. For them, it’ll just be native; just a Tuesday.

AD: That’s wild. Just Tuesday. But I don’t know, I’ve been having these conversations for a bit, and after every one, I feel pretty good. I think that’s a good sign.

AA: I feel like it’s a biased sample set of people you’re talking to—people who are more in touch with or thinking about humanity.

AD: True. But that’s who I want to be hanging out with. I wanted to come back to that idea: what makes for an ideal teammate for you in this new age? Who are you trying to work with?

AA: What you want to feel is that whoever you’re surrounding yourself with amplifies you and lets your edge flourish. This is somewhat intangible. Having an intellectual sparring partner who is a real person is very important. That pushback and conflict ultimately make you grow into a better, more purposeful version of yourself.

AD: In terms of craft, sometimes you ask AI to edit your piece in the voice of someone or critique it from their perspective. Are there specific people you ask it to emulate?

AA: Yes, depending on what I’m writing about. If I’m writing about startup topics, I’ll think about writers I like in that world. For example, Paul Graham is a big writer in the tech world. His style is characterized by brutal clarity and simplicity of sentences. If you ask an AI to critique in his voice, it will often point out the “fluff.” Other writers, like Eugene Wei, write a lot about social networks and have a framework-oriented approach with a lot of structure. It’s nice to get someone else’s perspective, because ChatGPT’s general perspective isn’t great.

AD: I like the idea that every company will be part media, part machine, and the best builders will be fluent in both. If someone isn’t fluent in, say, the media side or the tech side, how do you think they build that in this age?

AA: I think of these two things in concert as the language of the new era. To become fluent in any language, you have to immerse yourself. Be around people speaking it and doing it, and test it out yourself. For builders, that means playing more on the media side. For media people, it means actually making things and using the tools. The barriers to using any of this stuff are pretty low now. You can essentially make software like content, or “vibe code” it. So it’s a matter of wanting to immerse yourself and try things.

Not everyone will master both equally, but those who become competent in both and great at one will have an edge. Founders who are great at storytelling, or storytellers who are great at turning that into products or companies—if you can go in both directions, you’ll have more power than in the past when you existed only in one lane.

AD: It’s interesting hearing you say that. I’m definitely more on the storytelling side. What’s funny is that with storytelling, I think, “That’s hard to make good,” because I know a lot more about it. But when I think about coding, I think, “I can make that; it’s going to be great,” because I don’t know enough. The thing I know more about in storytelling is taste. That’s the magic word.

AA: The magic word these days. Title this podcast, “The First Talk on Taste.”

AD: You were talking about it pretty early though, right? You were one of the OGs.

AA: Well, some would say that. I wrote an essay last summer, a riff on Marc Andreessen’s blog post “Software is Eating the World,” called “Taste is Eating Silicon Valley.” I had been thinking about where tech is going and what becomes valuable in building products. If everyone can code and replicate products, then what’s left?

Distribution is one thing, and there’s an art and science to that. But as we automate more, even that is becoming more mechanized. The phrase “GTM engineering” has been coined, meaning distribution is becoming more technical. If you assume all of this can eventually be mechanized, then what is there?

I suggested that taste might be one of those things. It’s hard to define but can be understood in many ways. My one-liner is: in a world of scarcity, you want tools; in a world of abundance, you want taste. When you have so much, you need to choose what to align with or what represents your vibe or scenario—the more intangible aspects.

Taste is discernment expressed: informed judgment plus the courage to show it. It only exists once you make a choice. ‘Discernment’ as in having a judgment based on a strong set of references, understanding the differences between things, and being able to articulate why you like or dislike something. ‘Expressed’ as in you have to make choices;You can only demonstrate taste if you do something with it.

So it’s about discerning quality and then expressing it. Of course, it is somewhat subjective, but I’m curious how you think about that word.

AD: I think a lot of people have good taste but don’t realize it. They like things and if they had the confidence, they could tell you why. But they feel like they’re not allowed to, maybe because the thing they like is considered “dumb,” like a show such as Love Island. I think that can be good taste.

AA: That’s the antithesis of how people often use the word taste, which is to say that few people have it.

AD: Exactly. I think that feels weird to me. What I love is someone loving something. I don’t care if I think it’s terrible. There’s a lot of power in admitting you like things you’re not supposed to. That intersection of high-brow and low-brow tastes is where the “juice” is for a lot of my own work.

I think there’s so much judgment about what intelligence is. Intelligence and taste are like siblings. My wife watched Suicide Squad and really liked it. I was like, “I can’t believe you liked that movie. The movie’s so bad.” And she was like, “Why are you bothered? You haven’t even seen it.” I was being annoying. That happens a lot where it’s like, “How could you like that?” when the reality is, who cares? She liked it.

AA: I do think there is a part of taste that is somewhat scientific. Like visual-spatial intelligence, which is related to design sensibilities. You have to understand balance and how things are meant to be. There is a technical aspect to it that isn’t just a feeling or emotion.

One of my favorite pieces is Malcolm Gladwell’s “The Cool Hunt.” One of the maxims of the essay is that by the time you spot and name “cool,” it’s already moved on. Taste has that same slippery, compound of intelligence and intuition and expression — partly learnable, partly felt, and only partly explainable even if there’s a lot of fine details that go into it.

AD: Definitely. And in that one example of my wife, she’s a makeup artist and a visual artist, and the makeup in that movie is really good. Ok, let’s jump into the ways in which you are using AI in your work..

AA: The only thing that quickly came to mind, specifically with writing, is using AI for critique. Mostly, for a first, second, or third line of critique. I used to ask people for feedback using the ABCD framework: What’s Awesome? What’s Boring? What’s Confusing? And what do you not believe? I find that to be a helpful way to get feedback. Sometimes I do that with ChatGPT. It’s a nice first line because I get a little sycophancy. I tell it, “Tell me what’s awesome,” and I need to hear that before it cuts me down with the rest of it.

You know when you publish an essay and in the first two days that people are reading it, you find what quotes people pick up and what resonates with them. And sometimes it’s what you thought and other times not at all. Obviously I appreciate finding that out much more from people than I do from ChatGPT, but it is still useful.

The other thing, depending on what audience you are writing to, is asking yourself, who do you admire? Or what are the traits that you think are worth having a lens on your work through? Pick those five or 10 people and just be like, “hey, critique it through the lens of this person’s eyes.” And I find that to be quite helpful too.

And then honestly, not much more than that. It can get really tempting to go back for too many rounds of things, but for writing, I think that’s most helpful.

AD: Yeah. It’s funny you say that about the banger lines. I’ve been very shaped by Substack and their quoting feature. It feels a little dark because now when I write, I think, “That’s going to be a banger. They’re going to quote that.” And I don’t like that. I don’t like how my writing has been shaped by Substack in general.

AA: What else do you think has been shaped besides the quotable stuff?

AD: The cadence. I feel like I have to post a lot. I’m affected by the numbers. They changed their algorithm or whatever, and I feel like all my writing sucks now. That can’t be true, and yet I deeply feel it. This is just work I have to do. Substack was the first place where I really succeeded.

AA: The same thing happens on Twitter. The usefulness of your followers depends on the algorithm of the day, and that keeps changing.

AA: Before Substack, I thought in tweets. My brain became tweets. It changed how I thought.

AA: Substack is almost the inverse of Twitter in terms of expansiveness. I’ve been thinking a lot about how in the modern age, finding the medium of digital expression that you’re good at is like a rite of passage. Some people are really good in small groups. Some people are really good at thinking in tweets. Like Naval famously, right? And on TikTok, people invent formats, like the get ready with me videos and 60 second dances that other people imitate. On Substack maybe the diary entry or listicles. It’s a natural extension of what people always try to do, but it’s much harder when you’re competing in a global arena on platforms that are judging and amplifying. The presence of a “rising” leaderboard implies the presence of a “falling” leaderboard, which we don’t see.

AD: The presence of a “like” implies the presence of a “not like.”

I recently saw a quote from Ben, the CEO of GitHub: “It matters where you get your dopamine. Get your dopamine from clarifying your ideas more than from their visibility.” I plastered that on everything because I’ve gone way too far toward thinking, “Finally, people love it, they love me, here we go.” I’ve defined that as my first success, but it’s not sustainable.

AA: It’s a constant barrage. We’re only human, and it’s hard to keep it in proportion. You need people in your life who will judge you harshly in a loving way and also gas you up honestly to keep a balance.

AD: Totally.

AA: On the digital side, you usually know how good you feel about something internally before you put it out. Of course, sometimes you put something out that you didn’t think was great and people love it. Other times, you put something out that you thought was phenomenal, and it doesn’t get the same response. But most people have their own internal barometer. It’s helpful to hold on to that. People often ask, “What’s your favorite piece you’ve ever written?” I could just say the most popular one, but I like to hold on to a few that are not the most popular but that I feel strongly about. I wrote an essay called “The Great Movie Theory” and it’s not on my most popular list, but I feel strongly about the idea.

AD: How would you describe your relationship with AI? Is it an assistant, a partner, or something else?

AA: It’s probably both. Sometimes it’s an incompetent research assistant, and other times it’s brilliant. I like to think about it as an experimentation partner

AD: I like that. What do you wish AI could do, but fear it never will?

AA: It can’t take away human suffering. On a long enough timeline AI may be able to do almost everything else, but humans are the source of their own suffering, so I don’t think AI will ever be able to take that away, unless it lobotomizes us.

AD: Everyone’s making predictions about AI. Let’s make a prediction about humans. Where do you think humans will be in 10 years?

AA:I think we’ll largely be in a similar place, but just with more leverage and hopefully a lot of strides on the health side.

AD: What question about AI and creativity isn’t being asked enough?

AA: In some circles, there’s a lot of AI is at odds with creativity. It’s always helpful to ask the question: where exactly can AI augment creativity?

AD: What do you wish people talked about more instead of AI?

AA: I would say just talk more about people. I actually think we did that. So I wouldn’t denigrate our conversation. People — why we are who we are, why we do what we do, think how we think, feel how we feel. That’s the unifying thread.

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