Whoa: Conversations on AI & Creativity
Mills Baker, Seth Godin, Robin Sloan, Jasmine Sun, David Perell, Joan Westenberg, Venkatesh Rao, Anu...
AI is a tempting shortcut for people who must perform rather than speak their minds. Creators worry it produces disposable, lower-quality work and erodes craftsmanship. A premium market for truly human writing may survive.
6 Sep 2025
You remember when the iPhone came out? Nobody ran around saying you've got to get an iPhone. What happened is you would just see an iPhone and you would see how great the pictures were, whatever the hell, and you'd go, I want that. Nobody had to evangelize you or explain, well, what iPhone does is it co-locates super computing power in your pocket. Nobody would say shit like that, but that's how they talk about crypto and AI.
On the creative front, I don’t think the slop era is going to be meaningful. We've had these eras before where something suddenly gets cheaper or easier. Photoshop's a great example of this. There's this brief period, I remember in the 90s, where I would go online and I would look up graphics and I'd be like, “ooh, here's a picture of a mountain with lightning behind it how cool.”
Anytime you're angry about something and you're writing about it, you should try instead to write about the good thing. So if you're mad about something happening with a political development, instead you should write a post about how you think politics should go in an ideal world. If you're mad about a bad movie, you should write about a good movie instead. I just wish more people spent time writing about things that they loved, things that they admired, things that they thought should happen, not contra something else. Because that's how you get entangled in the nightmare of the world and become part of the problem.
It's probably the talking dog thing, which has two parts. Part one is if you meet a talking dog and its grammar isn't very good, don't forget that it's still a talking dog. It's still a miracle. But number two is just because a talking dog said it doesn't mean it's important.
I think you should begin by creating a series of documents in Word or TextEdit and describe your situation in as much detail as you can. Go on for pages. Write a five-page autobiography. Include your resume. Make a different document with all of your health history. Make another document with relationship history for business or personal things you're dealing with. Then, because remember, you could never do this with a person, when you're going to ask an LLM a question, upload the thing. No one's going to sit there and listen to you read five pages of background when you ask them a question. But AI will. So go spend an hour talking to Claude about that. And don't listen to people on podcasts. Listen to Claude, because it's read your five pages and I have not.
The thing that worries me, in addition to all the other things that worry me, is that Sam Altman has to pay back a lot of people a lot of money. And that always leads to organizations becoming evil, the way Google did. Watching Google become evil, shutting down companies like mine, doing things that they couldn't possibly be proud of, that's sad. And I think advertising will accelerate that. I'm hoping we can stay ad-free.
28 Sep 2025
To your question about what people starting out can do, I think there has been a crisis in criticism. I mean that in the most expansive way—not just hardcore criticism, but consideration of art. Think about the first album from some little band down the street from me. Who will write a review of that on the internet? No one. It was always hard to get attention, but I have this sense that a decade ago, there were more people consciously engaged in the work of telling you about new stuff. One reason that has fallen away is that recommendation algorithms have taken that role. So it's hard to tell people they should spend a lot of time doing that work because it's even less remunerative than making the art. But I try to do that in my own newsletter. I think it's something everybody interested in the future of art ought to be doing more of.
Here's a simple thing you can do when traveling to countries where they don't speak the language. For many years, I gratefully used Google Translate to capture the nuance of what I wanted to say. But it turns out that's not always what you want. I have a little prompt I copy and paste into Claude or Gemini. The prompt is basically: "I'm going to give you a phrase, and I would like you to translate it into Japanese (or any other language). I would like the tone to be extremely polite. However, I would like it to be as concise as possible because I'd like to say as few words as possible. If the meaning is about 70% correct, that would be fine. Please now show me the translation in Japanese script, in the official romanization, and then finally give me a phonetic pronunciation."
That's just what it's like being a human sometimes, I think. It's not that you are Zen, and therefore life is good. It's that every day you wake up and you try to be as calm as you can be and face life with the best energy and intentions that you can. Some days you'll get it right, and some days you won't. But you just keep on trying, which is very much like sobriety. I didn't quit drinking six years ago and then I was sober. Six years in, I wake up every morning, and honestly, I want a gin and tonic every day. Not a day goes past where I don't have at least one moment where I can't stop thinking about how good a gin and tonic would be. It doesn't help that I have a gin and tonic tattooed on my wrist. It's a constant reminder, but every day is a decision not to get a gin and tonic for breakfast. It's the same with everything else. You have to just keep on trying, keep on making that decision, and see what happens.
There's an art to trolling. AI won't create music like the 80s indie pop band Beat Happening, who sort of invented twee pop. Their music was so rough and sometimes off-key. They didn't know how to make music; they just made sounds they liked. AI is not going to do that because it makes music that makes sense. AI writes books that make sense. It's not going to sit down at a typewriter like Kerouac and just stream of consciousness write a novel. It can't be William S. Burroughs and print stuff out and cut it up with scissors and paste it back together. It won't do these things that are so weirdly, stupidly human. That means the opportunity is for humans to do human thing
I pretty deliberately don't use tools that have AI built into them. I use specific AI tools for specific things. For example, I'm not a big fan of Notion with its built-in AI. I like to draft a piece in Obsidian or IA Writer. A piece I write starts on my Freewrite, which is a smart typewriter without an internet connection. I sit at that writing desk and I draft a piece. Then I upload it to the internet, come over to my laptop, download that file, and put it into Obsidian, where I do my tweaks. Then I will take that text, put it into Claude, and say, "Can you generate some blog titles for this piece?"
I'm a big fan of using a specific tool to do a specific thing. I don't like to use hybrid tools. I like to have one tool for one job. I do a lot of things manually. There are workflows I've seen where I could automate the process, but I don't like doing that. I prefer doing things as manually as possible. I'd rather copy and paste something from Obsidian into ChatGPT and then copy and paste it out than connect it all up and have it flow through the apps. I can't exactly articulate why I prefer doing it that way, but I just like being the human in the mix. I'm a believer in friction. Faster and smoother is not always better.
I wish people spent more time talking about things they love. I wish people would say, "I fucking love this thing that I found, and here's why." And I wish that people reading that would go, "That's cool that you love that. Here's something that I love," instead of going, "Fuck you for loving that thing." I just wish we spent more time talking about the things we love. I am 100% guilty of not doing that, and I want to be better at it.