This is the Sublime newsletter, where we share an eclectic assortment of ideas curated in and around the Sublime universe.

In case you missed it… we released our annual zine: Whoa, Vol. 2: Conversations on AI and Creativity. We’ll be releasing one conversation here each week.

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A conversation with Joan Westenberg

This was my favorite conversation in the entire series.

I agree with Joan’s takes on basically everything. I also like the way she expresses things — it has a very calming effect on my nervous system.

I first heard of Joan Westenberg when her article I deleted my second brain went viral. She then posted on LinkedIn that sublime is the only knowledge tool she enjoys and now I love LinkedIn and I love Joan.

Here is the link to subscribe to her work.

In this conversation, we cover…

• The dangers of AI as a yes person

• Why she prefers copy-pasting over automation

• Her simple philosophy on creative work and why she doesn’t care if a robot wrote it

• Why being unpredictable is the best defense against AI

• and more…

Or listen on Spotify and Apple.

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

The edited transcript

Alex Dobrenko: I’m excited to talk to you. I love your takes on basically everything. I feel like you kind of just appeared out of nowhere—at least in my view. Everything was going on and then Joan was everywhere. It feels like a takeover of LinkedIn.

Joan Westenberg: It’s weird because I’ve been writing online for well over a decade. You never know when you’re going to get traction and break through. You don’t know what piece is going to do it, but hopefully, if you show up long enough, it starts to work out.

AD: Do you feel like there was one piece that made it happen?

JW: Yeah, it was my essay on deleting my second brain and moving away from knowledge management systems. It hit a nerve for people because a lot of folks feel like they’re failures just because they don’t have a perfect second brain knowledge management graph. That’s an awful way to feel about yourself—to feel like you’re getting your life wrong because you don’t have the right number of connected notes.

That one resonated with people. It’s funny though, it’s not my first go-around. I had a blogging career before, and about a decade ago, I burnt the whole thing down and started from scratch. It’s been interesting doing it all a second time.

AD: Why did you burn it all down?

JW: There are two answers. The smarter answer is that I felt like the stuff I was writing had drifted into the territory of just trying to write what people wanted to read. I had a piece go viral because Craig from Craigslist shared it, and then I went down that easy-to-fall-into trap of just writing the same thing because that’s what I thought people wanted to hear.

The dumb answer is that I was drinking really heavily at the time. I got really drunk one night and deleted all of my blogs and social accounts, losing hundreds of thousands of followers in the process. That’s what drinking a lot will do to you—it’s not good. After I eventually sobered up and realized I did want to get back to writing, I had to build it all over again, which took a few years.

AD: Don’t drink and blog, folks. So this conversation is broadly about AI and creativity. What’s your AI vibe?

JW: Broadly, I would call myself a humanist. I’m a big believer in human potential and in humans doing human things. Whatever we do with our work, the things we create with each other, we have to make sure we keep as much of our humanity in the loop as possible. Because if we don’t, I’m not sure what the point of any of this actually is.

When it comes to AI, I tend to see it as a tool. It can be a tool for great things or really crummy things. It can be a tool for cool people and terrible people. It can be used ethically or very unethically. But it’s very much a tool in the same sense that everything else is a tool.

What we do with the things we invent, with the technology we invent, with the tools we have, is what defines us. It’s not the tool itself that does that work.

I think back to really early technologies, thousands of years ago. We discovered fire and invented use cases for it. Some of those use cases burned down London, and some just kept families warm. Fire itself is pretty neutral. We invented the wheel. We did really cool things with the wheel, but the wheel also enabled mass warfare.

It’s what we do with these tools that matters more than the tool itself. I think tools are broadly pretty neutral. It comes down to what we do with it.

AD: I’m curious, how do you stay as a human in your loop? Practically, what do you use AI for? What do you find it useful for?

JW: I use AI to do the things I hate. That’s really my rule of thumb. I hate coming up with titles for videos and essays, so I’ll absolutely use an AI tool to generate a whole bunch of titles that I can test out on my blog and YouTube. I really hate editing videos. It’s not something I’ve ever enjoyed. So I will happily use a tool like Descript to edit a video for me.

I don’t like making graphs and charts, and I don’t like making slides. So I use things like Eraser and Gamma to do those tasks for me. Anytime there’s a task that I hate doing, that sucks the life out of me, that’s when I will reach for an AI tool.

On the other side, there are the things that I love. I love sketching and drawing. I love making and editing music. Most of all, I love writing. These aren’t things that I have any interest in outsourcing to an AI because I want to do them. I really do want to sit down and write. That is something that I look forward to every day.

There’s no way I want to just throw that out to an AI because I’m passionate about it. It is a good time for me. I look at it in the same way as, you know, I enjoy playing video games. I wouldn’t set an AI bot to play my video games for me because I enjoy the thing. I want to do the thing.

That is my simple calculus: I will let AI do the things that I don’t want to do, and then I will do the things that I want to do.

AD: Okay, I love that. I really like the video game thing. The complicating factor for me and a lot of creatives is time. I don’t have enough time. I have to work; I don’t have enough time to do it, so let me see if I can get a little shortcut and have AI help me a little bit. Does that happen to you? What about the more intellectually deep stuff, like having it review a draft and push you on ideas?

JW: I don’t trust AI to review my drafts or to push me on ideas because AI tends to just tell you what it thinks you want to hear. If you get a bunch of feedback on a draft and then you just reply to the feedback and say, “That feedback is wrong,” the AI will say, “You’re absolutely right. Here’s the opposite of that feedback.” You can’t trust it to give you a proper review because it can’t believe the things it’s telling you.

If you send me a piece and ask for feedback, the feedback I give you is stuff that I believe to be true. If you push back on it, I’m going to push right back on you because I have read this piece and I have formulated an opinion on it based on my values, beliefs, and experiences. You can trust that it’s coming from me.

If you have an editor or a review partner who is just a “yes” person, which is what AI is going to be, the quality of what you create will not be good.

I probably have a degree of privilege with my writing because it is most of what I do. It’s not like I have to squeeze in a few hours here and there to try to write my opus. I make a living by writing, and the writing is the core of it. So I don’t find myself trying to find a shortcut necessarily, because the writing is the work.

That being said, I can understand if writing is not the biggest priority for somebody. If their job is being a dev and they also need to write about the thing they’re building, I can understand them using an AI tool to do that. I don’t actually have a broad philosophical problem with somebody using an AI writing tool, but I do think the onus is on that person to make sure the humanity isn’t stripped away from their work.

If you write a piece of software and then use an AI tool to generate all the docs for that software, you still need to go through and read what has been generated and edit what has been generated. I don’t mean edit it to sound less like AI; I mean edit it to be true, valuable, and useful.

AD: That idea of responsibility feels really important. I’ve heard that from a few people in different ways—that you are responsible. You can’t blame the AI; it’s you.

JW: Yeah, the buck stops with you. I don’t really care whether or not somebody used AI to write something that I’m reading. I care if what I’m reading is good. If I enjoy what I’m reading, if I like it, if it resonates with me, if it makes me feel something, that’s what I care about. If it doesn’t do those things, then it is a piece of crap.

I also broadly think that if a piece of work is generated entirely by AI and is good, then I can probably enjoy that. But I’ve also read a whole lot of things written entirely by humans that I didn’t enjoy. Things are good or they are bad. I don’t think that is dependent on the tool used to produce it.

An Aphex Twin album produced on an Amiga is not better than something recorded on tape by the Beatles just because of how it was made. I don’t think something produced today on Ableton is any better or worse than something produced in the 90s on the software they had at the time. It all comes down to whether or not it’s good.

AD: Why do you think so many people have such a problem with consuming AI-generated stuff?

JW: I think part of it is a deep existential fear of being replaced. For creatives—writers, designers, music producers—who have spent the last 30 years having their work devalued by a lot of folks in tech, this makes a lot of sense. People aren’t afraid of being replaced in a vacuum. They’re afraid of being replaced because a lot of folks in tech have spent the last 30 years trying to replace or devalue them.

We’ve gone from an album costing 10 or 20 bucks, and a musician gets paid when someone buys it, to artists not being able to make a living because all of their music gets streamed on Spotify. When you feel that in your bones, when you feel how much has been taken away from creatives, it’s a very understandable human reaction to say, “Is AI going to make this worse? Is AI going to replace the very act of creation?” It’s not so much a fear of consuming AI content; it’s a fear of being replaced and the human being removed from the equation. It’s a very valid, understandable fear. Tech has done a lot of disservices to creative industries.

AD: What advice would you have for people who fear that?

JW: There’s not a whole lot that can be done to stem the tide of technology. It’s not to say that you should just abandon all hope or abandon your humanity, but attempting to hold back the tide probably won’t work.

You can make decisions for yourself. If you’re an artist, I think you’re better off focusing on creating the art you want to make and doing it the way you want to do it and sharing it the way you want to share it. Put your energy into that instead of putting your energy into hating or trying to fight against AI, because one is creative and the other is reactive.

I don’t think you’ll have a happy life if you dedicate however much time to trying to prevent ChatGPT. I understand this is a really scary time. Economic anxiety is at a massive high. Housing affordability is screwed everywhere around the world. Jobs are disappearing. Incomes have not risen in line with the cost of living. All of that is terrifying for a lot of people.

But I don’t think that fighting against AI is going to stop any of that or fix any of that. I think it’ll just burn a lot of energy and leave a lot of folks feeling pretty disheartened and lost when they can’t fix it all. The best thing you can do as a creator is create. Do it your way, do it how you want to do it. Do it because you’re passionate; do it because you love it. Make what you want to make, and then trust that you will either find an audience or you won’t. And that’s pretty much all you can do.

AD: Right before this, I was watching your Output Native video on YouTube. It made me think of this. The one thing that’s hard for me and for a lot of people is that a lot of people who work online—a lot of artists in general—need the audience. They do it for the audience. I’m curious how you think about that. You have an active audience on LinkedIn and YouTube, and it seems like you’re in conversation with it. How much is that true?

JW: I would be doing what I do regardless of whether or not I have an audience. That’s borne out by the fact that I have a whole lot of creative things that I do that other people just have no idea about. I have an entire noise music project that people don’t know about because I don’t really tweet about it or promote it. I just make stuff and put it online, put it on SoundCloud.

AD: Really? I didn’t know you were into music at all until this conversation.

JW: Yeah. I spent years as a touring musician. I’m a trained audio engineer. I have a whole life in music. I’ve always loved music, and to this day, I still fire up Ableton and work on drone noise scape stuff. I do it because I want to make it, not necessarily because I want to play stadiums. I do it because I care about it.

With the writing, I’ve been writing online for over ten years now. I would be writing if it all went away. It’s what I do. At the end of the day, there’s a lot of crap out there that you have to deal with when you create anything online. I’m sure I would have a much happier life in some regards if I hadn’t dropped out of law school, but I did drop out of law school, and I did it to do this. If this all goes away, it all goes away. We’ll find out what happens.

I have a relatively world-hardened approach to this, where things have been hard, and I know what it’s like for things to be hard. I would rebuild again, because I’ve done that before; I literally deleted everything in a drunken fit. So I do know what it’s like to start from scratch because I’ve done it twice.

AD: It’s funny, today the question popped into my head, you know how everyone’s always like, “What would you do if you couldn’t fail?” I feel like a much better question is, “What would you do if you knew you were going to fail?” That seems like a better question.

JW: I operate on the basis of “we’ll see.” You never know where things are going to turn up.

AD: Are you a spiritual person? You seem very Zen. Very even-keeled.

JW: It’s easy to think that if you don’t live with me. I’d like to be Zen, but you’d have to ask my kid, my partner, and my two cats if I’m actually Zen. They’ll know. I think I have my moments. Every now and then, the existential dread gets to me, or the dishes pile up, and all I can see are dishes. In those moments, I get very stressed.

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.

AD: I feel calmer just talking, having this conversation. You’re settling my nervous system. Thank you.

JW: I’m glad, I’m glad.

AD: You said that absurdism and shitposting are a defense against AI. I think that could be good advice for creatives. I’d love for you to elaborate on that.

JW: AI will mostly make what makes sense because it produces based on its consumption and training—based on the mainstream, based on the entirety of human history. It is the sum of who we are. So it will make what is most expected. But I think that means it can’t make what is weird. It can’t make things that are truly weird because it doesn’t know how and can’t really go against the weighted sum of what humans generally tend to create.

As a whole, yes, it can produce things that will rival Katy Perry’s greatest hits. It can produce books that will rival James Patterson’s greatest novels. But I don’t think it will ever produce something like Merzbow, Japanese noise music made from the sounds of seals and distorted drill bits. It won’t make that because it’s not what most people want, so it’s not what it’s trained on. I think the things that are whacked out and completely unexpected will always come from a human. I don’t think AI can necessarily do what is completely unexpected; it wouldn’t think to do that.

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 things.

AD: The thing that makes me feel okay is that if AI did ever do that stuff, then those people wouldn’t do that stuff. If AI cut up paper into poems, William S. Burroughs would have done something else.

JW: I am always reminded of Jurassic Park: life finds a way. The human in us is always going to find a way. I don’t know what it will look like, but it will find a way.

Most people are probably going to want the mainstream, the slick. Most people will want that, and you know this because most people want Katy Perry. They don’t want Beat Happening. But there will always be some people who want Beat Happening.

AD: You also run a comms company. What do you say to founders and companies as they try to figure out their existence in the world?

JW: It’s hard to find a general response because everyone has a different experience. My job is to help people shape a message and then share it. I don’t tend to work with people if I don’t think they have a message worth sharing. But I do emphasize the human element. For example, there are a lot of PR platforms that use AI to generate lists of reporters and scrape the internet for their contact details. They use AI to generate pitches and send them. And then the journalists use their human intuition to read that slop and say, “Fuck that company. I’m never going to cover them because they can’t treat me like a human being.”

A lot of my friends are journalists, and they hate the way AI is swamping them with information. To stand out, you’ve got to be a human. You’ve got to be a person. You’ve got to treat other people like they are people. I think you can extrapolate from that a pretty clear principle: whatever you’re doing, you have to treat the person on the other end like a person. And that’s what matters.

AD: Alright, can you walk me through some of the ways you use AI.

JW: 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.

AD: You seem so confident in what you believe. Do you ever doubt yourself or your beliefs?

JW: I firmly believe that there are better ways of doing everything that I do. And I firmly believe that there are better tools than the tools that I use. The thing is, you can spend the rest of your life chasing that, because there will always be a better workflow and a better tool. You can spend the rest of your life jumping from one amazing tool to the next.

For the most part, note-taking apps let you do the same thing, which is writing down some notes. Whichever one you want to use is fine. The best tool is probably the one that you’ve got, and that’s okay. My brother is a philosopher and a speechwriter, and he doesn’t use any of these tools. He uses a notebook and writes everything down by hand, and he gets about as much done as I do.

It’s not that I know that my way is right; it’s that I know my way is wrong. I know my way is probably inefficient, and that everyone else probably has better ways of doing things than I do. But that’s okay. It’s okay.

AD: How would you describe your relationship with AI?

JW: It’s an employee. I pay it to do things for me that I don’t want to do. I wouldn’t say I have a relationship with AI. I don’t have any kind of connection to any of the AI tools, agents, or platforms that I’ve ever used.

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

JW: Disagree with me. I’d like AI to be able to disagree with me and tell me why I’m wrong.

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

JW: “Are you happy?” Are you happy with what you’re making?

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

JW: 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.