![[8-Steph Ango.png]] *Dialectic Episode 8: Steph Ango - Tools for Amplifying Our Light - is available on [Spotify](https://open.spotify.com/episode/5RDXPYjvNWqK933eHQNhHP?si=KKCxOuCdQEqbil-TA66ZyQ), [Apple Podcasts](https://podcasts.apple.com/us/podcast/8-steph-ango-tools-for-amplifying-our-light/id1780282402?i=1000688771368), and [YouTube](https://youtu.be/TDP8qzVK5XQ?si=p8b0ps-9NZumj-Uo).* <iframe style="border-radius:12px" src="https://open.spotify.com/embed/episode/5RDXPYjvNWqK933eHQNhHP?utm_source=generator" width="100%" height="152" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe> <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/8-steph-ango-tools-for-amplifying-our-light/id1780282402?i=1000688771368"></iframe> <iframe width="560" height="315" src="https://www.youtube.com/embed/TDP8qzVK5XQ?si=qQxyrqBFmSWYbkzw" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> # Description Steph Ango aka Kepano ([Website](https://stephango.com/about), [X](https://x.com/kepano)) is a designer, writer, entrepreneur, and toolmaker, best known as the CEO of [Obsidian](https://obsidian.md/), a powerful and flexible writing and thinking tool. Steph's education is in biology and industrial design, but he is true [multi-hyphenate creative](https://stephango.com/projects), working across mediums including software, hardware, supply chain and packaging, words, wood, furniture, ink, color schemes, open-source systems, video, podcasts, and more. Above all, he makes tools—deeply opinionated ones—designed to reduce friction for himself and others in the act of creating. Steph joined Obsidian after initially contributing as a fan and enthusiast and impressing its co-founders, Shida Li and Erica Xu. Under his leadership, Obsidian has grown into one of the most beloved and powerful independent software tools in the world, with millions of users. As a daily user myself, I rely on Obsidian for my research and thinking for this podcast. Before Obsidian, Steph founded [Lumi](https://stephango.com/lumi) and [Inkodye](https://stephango.com/inkodye), the former of which was acquired by Narvar. Beyond design, Steph is one of my favorite writers. His concise, sub-500-word [essays](https://stephango.com/writing) have shaped my thinking on design, software, learning, agency, constraints, and creativity. While we couldn’t cover all of his ideas in this conversation, we explored many of them in what became my longest conversation to date—one that is packed with wisdom. I believe these ideas will challenge you in unexpected ways and push you to be more creative, agentic, and optimistic. # Timestamps - (1:56): Constraints and style - (11:51): Aggressively planting creative seeds but being patient for them to grow - (17:42): Stadium of past and future selves - (22:34): Asking what can be removed and making incremental progress - (28:47): Building a product and company (Obsidian) with the "constraint" of ideology and principles - (38:52): Using Obsidian makes Steph better at building Obsidian - (44:09): What makes for good design and seeing the world as something designed (by nature or man) - (53:11): What makes a good tool? - (56:20): Thinking tools and Obsidian - (1:04:32): "In good hands" and caring more than anyone else - (1:21:38): Engaging all five senses - (1:24:46): Creating cohesion or your own cinematic universe - (1:30:43): How to time travel - (1:33:08): Designing for digital durability or permanence & "File over app" - (1:56:46): Investment and "selfishness" in extending your light - (2:05:54): Choosing problems to work on - (2:09:10): "Nibble and your appetite will grow" - (2:12:31): Compounding - (2:19:55): "Caloric energy is precious" - (2:26:21): "Earth is becoming sentient" - (2:39:31): Busy being born and sharing along the way - (2:42:11): Love and freedom # Links - [Style is consistent constraint](https://stephango.com/style) - [Buy wisely](https://stephango.com/buy-wisely) - [Stadium of selves](https://stephango.com/stadium-of-selves) - [What can we remove?](https://stephango.com/remove) - [File over app](https://stephango.com/file-over-app) - [Obsidian Manifesto](https://obsidian.md/about) - [In good hands](https://stephango.com/in-good-hands) - [Pain is information](https://stephango.com/pain) - [Quality software deserves your hard‑earned cash](https://stephango.com/quality-software) - [Don't delegate understanding](https://stephango.com/understand) - [Nibble and your appetite will grow](https://stephango.com/nibble) - [A little bit every day](https://stephango.com/a-little-bit-every-day) - [Caloric energy is precious](https://stephango.com/precious) - [Erewhon](https://www.goodreads.com/en/book/show/516570.Erewhon) by Samuel Butler - [Earth is becoming sentient](https://stephango.com/earth) - [Agents of chaos](https://stephango.com/agents-of-chaos) - [Concise explanations accelerate progress](https://stephango.com/concise) - [Always learning, always teaching](https://stephango.com/always-learning-always-teaching) - [Six definitions of love](https://stephango.com/love) Dialectic with Jackson Dahl is available on all podcast platforms. [Join the ⁠telegram channel for Dialectic⁠](https://t.me/dialecticpod) [Follow ⁠Dialectic on Twitter⁠](https://x.com/dialecticpod) [Follow Dialectic on Instagram](https://www.instagram.com/dialecticpod/) [Subscribe to Dialectic on YouTube](https://www.youtube.com/@Dialectic) # Transcript **Jackson** [00:00:00] Welcome to Dialectic, Episode Eight, with Steph Ango, aka Kepano, as he's known on social platforms. He's a designer, writer, entrepreneur, toolmaker, and CEO of Obsidian. Obsidian is one of my favorite products. I use it every day. It's a robust note-taking and thinking tool that uses bi-directional linking and an extensive plugin system to become one of the most powerful and extensible tools around. **Steph**'s background is in biology and industrial design, but he is one of the most dynamic and multifaceted creatives and designers I've ever met. He's worked across software and hardware to supply chain and packaging with a former company called Lumi. He's an amazing writer. He's worked with wood and furniture. He innovated in printing styles with a former company called Inkodye. He's created his own custom color schemes and design systems and other forms of web and open-source systems. He's made podcasts and videos. He truly is a polymath, and this is one of my favorite conversations I've had so far. More than anything, he sees himself as a toolmaker, and I think you'll see that in our conversation, in the way he sees the world and designs for removing friction, making creativity more possible. We discuss many of his ideas and talk through several of his short essays, which have really pushed my thinking. We talk specifically about design and software, learning and agency, how to use constraints and style. **Steph** is truly wise. He is so energizing to spend time with, and he is prolific creatively. He's an amazing Twitter follow as well, and I would strongly suggest reading his writing after you've enjoyed the conversation. I believe this conversation pushed me and will hopefully challenge you to be more creative, agentic, and optimistic. Here's Steph. **Steph** [00:01:53] Ready to rock. **Jackson** [00:01:54] Let's go. I'm really glad to be here with you. ## [00:01:56] Constraints and Style I want to start on a theme across your work and writing. That seems to be one of the main reasons I experience you as being very opinionated in a good way. And the theme that seems to run across and maybe enable that is you really are thoughtful about constraint, whether that be professionally, creatively, in writing and design. I think this applies to stuff like Obsidian's company structure and some of the ideology and principles behind it, your writing and your brevity, but also frankly, just across your design thinking. I'm curious why constraint is empowering to you. **Steph** [00:02:37] Yeah, that's interesting. I don't know when I started imposing constraints on myself. I feel like constraints just naturally occur from the medium. Like, if you're writing a tweet, there used to be a limit to the number of characters that you could write. Or, if you go to my projects page on my website, some of my oldest projects are Winamp skins from the early 2000s. We're talking Winamp 2, which is before they let you do whatever you want with shapes. So, you had to work within a certain number of pixels just to do a volume slider. You had so little that you could do, but yet that's where all the creativity came from. I would look at some people who I thought were amazing Winamp skin artists back then and I was like, "How did they figure out how to put this entire little animation in a movement of 12 pixels?" That would fascinate me, and I would just think about that and try to come up with something myself. So, I think maybe that's where it started, just out of necessity. Those constraints shaped the way that I design things or think about things. But then, over time, I had eras where I had less constraint. My previous startup before Obsidian went down the VC path. We had a lot more money than any other project that I had ever done before. In a way, I missed having those constraints. The lack of constraint, in certain cases, led us down decisions that were not as good as if we would have those constraints. And so, now I'm always looking for how I can add forceful constraints into my own process and pick good constraints that I think I can live with, that I can have fun with, and that becomes a canvas to experiment within. **Jackson** [00:08:08] Yeah, it seems like obviously you've done a lot of work in the physical world, too. But in digital space, it's funny you bring up the earlier Winamp example. Digital space, video games, software all over the place: tons of constraints. Basically, the last 20 years has been a continuous removal of constraint, or at least a continuous expansion of what you can do. So, I find it particularly interesting that some of your clearest forms of constraint are almost purely fake—or not "fake," but "imaginary"—or self-imposed. Short writing is a simple example. Most people, I think, outside of Twitter, their only reason to do writing outside of Twitter would be long-form. And yet you're doing shorter form. Is that something that requires discipline, or is it actually just like, "Oh, I know the freedom," or, "I know the way it's empowering on the other side, that it allows me to show up more consistently?" **Steph** [00:08:08] Yeah, well, it's definitely self-imposed. But then it's the element of a style. Basically, I think you want things, in general, to be recognizably you and to become easier and easier for you to do. Writing is difficult if you have no constraints. If you know that, okay, I'm going to try to fit in this idea in 500 words, then you know the kinds of things that you're probably not going to write about. A lot of my essays have no reference material. There are no footnotes. It's just like, I'm stating things. This is my opinion. With my essays in particular, I'm writing to a younger version of myself. I'm imagining that the only thing I can pass on to this younger version of myself is X number of words. Here's the most concise way I can communicate this across time to this younger version of myself. So, the conciseness comes from the fact that I know that I wouldn't want to read something long back then, especially. **Jackson** [00:24:24] Probably most of us still. **Steph** [00:24:49] Yeah. **Jackson** [00:07:03] One of the cooler things when I was reading a bunch of your stuff, I was loading it into a "read it later" app. There's something with the rendering where occasionally I would get presumably what was an older version of one of your older pieces. **Steph** [00:07:20] Oh, okay. **Jackson** [00:07:20] And I could see the culling. **Steph** [00:07:24] I removed some words. **Jackson** [00:07:25] Yeah, it was really cool. **Steph** [00:07:26] This is one thing that is kind of weird about my blog: I will edit old pieces all the time. I don't put "last edited" or "versions" or anything like that. I just don't care about the continuity of it. I'm trying to make each one really good. Oftentimes what happens is I'll write a new essay and I try to link very profusely to other essays, because they all kind of build on each other. And when I link, I go to that essay, and it's 10 years old now. And I'm like, "Damn, I could have done this way better." Most of the time, it's just too wordy, and I can simplify an idea. A lot of the words I remove are just connective words that are unnecessary. They don't actually have any calories in there. So I'm trying to get rid of that. Recently, at some point when Twitter stopped letting you link to things, I started putting screenshots of all my essays. I wanted the screenshots to have a certain feel to them so that people, when they saw it, would think, "Oh, hey, that's from Capano," and they would just instantly notice that it feels like one of my essays. So, I came up with this color scheme. The color scheme has basically nine colors, and now I've been using that color scheme for all kinds of stuff. Lately, I've been teaching myself piano, and I've been using these colors to make these little tools for myself to help me bridge synesthesia with the way my brain works. I'm trying to connect colors to notes so that I can learn them more easily. But I have this set of colors, so now it's like, okay, I'm just going to use those colors. And then by default, it's going to fit into everything else that I did. And so it just becomes a sort of signature. It's a little scary. I remember always wanting to do something like this, but I was afraid that I'd have to stick with something that I would eventually not like. **Jackson** [00:09:36] Something like this being the brevity or the color scheme? **Steph** [00:09:39] The color scheme, or even the design of my website or something like that. I felt like the continuity was so important to me, that I had to get it right, because otherwise, then I'm stuck with something that I don't like. It's the same reason that it's really hard for me to imagine myself getting a tattoo. I would have to feel really great about it. I've known people who have lots of tattoos, and they're like, "Oh yeah, this one sucks, but it reminds me of a different time," or whatever. And I like that notion, too. **Jackson** [00:10:09] Yeah, that's ironic. It's easier to relate to your digital self in that way. There's less permanence. The other thing that's so powerful about having consistent visual language online, but also brevity, is in a world where increasingly, you think about old Twitter, somebody followed you, they were pretty likely to reliably get your content because they opted into it once. That's not really how, certainly not how TikTok works. Increasingly, it's not how Twitter works. And yet you're almost hacking that. You're giving people, we were talking before we turned the mics on about using not your face as an avatar. There's a similar thing there, which is it's a little mental visual cue for somebody to kind of go, "Oh, I've seen this before. Oh, I like that guy. Oh, that guy with the little beige face. He had interesting ideas. I read a short screenshot essay from him." And that compounds in a way that I think is actually the way to build a following or a brand on the modern internet, where every incremental piece of content needs to almost earn its place. **Steph** [00:11:15] Yeah, it's like when someone that I've been following for a long time changes their avatar, it's like they have to start, I'm like, "Who are you?" **Jackson** [00:11:23] Your friend had super long hair and they got a crazy haircut. **Steph** [00:11:26] We have to start all over from scratch now. Yeah, I totally agree with that. You've done the same with your color scheme. I know when I see that little pink circle, I know that's you. **Jackson** [00:11:38] But to the tattoo point, it's like now, if I ever want to change it, am I undoing everything? And so this is the other thing I respect about you a lot. You're someone who is so thoughtful about this stuff, but also doesn't default to weight, at least from my vantage point. ## [00:11:51] Aggresively planting creative seeds but being patient for them to grow You're so generative, you're so prolific in how much you create. I'm curious how you balance that very concrete style, very constrained, but also it's just like, I don't know, you put out something today or yesterday about your piano thing. It's just constantly happening. **Steph** [00:12:09] Okay, so the thing is, when I, if you look at my website and you look at the timestamps on the essays there, there's like one a year. I started my first blog in 2005, so there's a lot of stuff. **Jackson** [00:12:29] The oldest one on there now, I think, is 2012, at least the oldest one under linked favorites. **Steph** [00:12:34] Yeah, that's pretty old, I guess. I have some older stuff that I'm culling over time. There might be some good stuff that has been removed that might deserve to be back on there, but yeah, so there was a long period of time where I basically wrote a blog all by myself to myself for 10 years. **Jackson** [00:12:58] Totally, or just no one knew about it. **Steph** [00:12:59] What I did was I made a blog and I had it in private mode because I wanted to set up the visual language, start writing, and have a few good posts before I launched it. Then I just never launched it. So I just wrote, and then I kept writing, and then that became my note-taking app in a certain way: this private blog that I was writing to no one. At some point, a few years ago, I thought, "Okay, I really should start publishing stuff." I had this archive of 10 years of drafts. Some of them were really good, and I still felt good about them. So I think a lot of the process is just planting seeds and waiting for those things to reach a certain maturity where I can look back at them a year later, five years later, and I'm like, "I still agree with myself. Therefore, I should post this." And by that point, I have a clear idea of what the thing is. I do use social networks like Twitter to put the messiest stuff up and see if people disagree. Then I get some good friction from that, which I use to catalog arguments against what I'm saying or try to refine my language. That just goes into drafts. Then sometime later, something happens and I'm like, "It's time." That idea just came back, and I have all the context necessary to just spit it out in a very short burst. It's really hard to do that. It's very frustrating when you're younger. I had a similar thing. I created the series off a blog post called "Buy Wisely." It was basically making the argument that you should buy more reliable, durable things that will last you for a long time and that the extra cost of it will end up being worthwhile. So I made a few recommendations of products that fit that description to me. When I was doing that, I did a bunch of self-research on things that I've owned for a long time: How many times I've used them, how much did they cost me at the time? I tried to understand the cost per use. I did this whole spreadsheet and looked into all of these objects that are still with me. There are some new things that I've owned for one or two years where I feel really good about how they will last, but I feel like it's too early to say. My rule for anything that I'll share is: I'm still using it five years later. **Jackson** [00:15:58] You'll share as in recommend? **Steph** [00:16:00] Yeah, exactly. And so it takes five years for one new post to be added to that. **Jackson** [00:16:11] It's a filtration system. **Steph** [00:16:12] Yeah, it's kind of frustrating in some ways. I have some things that I've incorporated into my life in the last couple of years, but they're not allowed in my constraint system because I haven't had them for five years yet. **Jackson** [00:16:24] It's a really cool blend of baseline generativeness or generativity around creating things, liking things, and trying things. It has maybe an insulation, whatever it is that you need to both keep enough distance from it that you can evaluate it maybe not objectively, but a little more objectively, but also have the freedom to create. I think even going back a little bit, the idea of having a private blog or something like that, I think people get caught on one end of that spectrum a lot. They either are constantly sharing everything; there's no filter, there's not a lot of signal. Or they're hesitant to share anything. It seems maybe somewhat deliberately and somewhat accidentally, you've created an interesting kind of amorphous filtration system that allows for all the good on both ends. The creating, like Rick Rubin, create something for yourself and then share it with the world. That is okay advice, but it's hard advice to take. It feels like in some ways you're manifesting some of that in a cool way. And by the way, I've experienced this where you go back and read something that you didn't think was very good and you're like, "Wow, I actually see the wisdom there." ## [00:17:42] Stadium of past and future selves One of the other ideas I love of yours that I think about a lot is the audience of selves, the stadium of past and future use. **Steph** [00:17:49] Yeah. **Jackson** [00:17:49] This is sort of like you creatively negotiating with all of those and working together to figure out how to get to the best stuff over time. **Steph** [00:17:59] That idea is basically, if you think of yourself as, let's say you live 80 years, each new day is one person, it would fill up a stadium. It'd be however many 50,000, 60,000 days in that stadium represents 60,000 people. Your current self, today's self, is on stage. You're in the middle of the stadium and all of your past and future selves are sitting in the audience. So there's like baby you, there's a one-day-old version of you all the way to 80-, 90-year-old you. They're all sitting. In my stadium, I don't know how they're seated. I think they're at random. I've talked about this with other people and they're like, "Oh yeah, in my mind stadium, they're all sitting in chronological order." So there's a baby section, there's an old me section. **Jackson** [00:19:03] I like that you can imagine looking to the part of the stadium. Oh, I'm appealing to my five-year-old self in this moment, all 360 of them. **Steph** [00:19:11] Basically, anything I've ever really tried to create was for a version of myself. That makes it a lot easier in a way, because the more I've gone in that direction, the more I find that other people respond to it. I have a real problem trying to learn musical notation. It doesn't make sense to the way my brain works. I want to get good at sight reading, and for some reason, musical notation is really problematic to me. So I'm trying to figure out solutions to help me with that. I've been posting some ideas, and then other people are like, "Oh yeah, that's cool. That would help me." People are also in the same situation that I am, or they're teachers trying to teach students how to sight read. They're like, "Oh, I could use this with my students." This is just a trope at this point, but it's like, yeah, make something that you would enjoy. You know yourself well, and you're unique, but a lot of people have the same problem that you have. So if you understand that problem well, then other people will probably enjoy whatever solution you come up with. **Jackson** [00:20:37] Making something for yourself is obviously an empowering constraint. Maybe what's so powerful about the way you talk about it is by orienting it around past selves or future selves, there's a separation that allows you to... Sometimes it's like, "Oh, make something," but what does that even mean? **Steph** [00:20:59] What is this? **Jackson** [00:21:00] It's almost like the idea of being able to go back to something you wrote in the past and reduce it, making it even more clear. It's almost like the older, wiser version of yourself going to that young self who was energetic, had the idea, and wanted so much to say about it but didn't quite have the words. You can almost imagine that person, the older you, putting your hand on the shoulder and saying, "Here, let me help you word this." It's a really beautiful metaphor that I think is still anchored around that constraint of the audience of one, this pretty common idea. **Steph** [00:21:32] Yeah. **Jackson** [00:21:32] But it's a cool tweak on it that I think is helpful. **Steph** [00:21:36] People ask this question, "What piece of advice would you give to your younger self?" It sounds so grandiose, but some of my things are just like, "This is the kind of shaver you should buy," or, "This is how you should meal prep if you want to not be hungry at 1:00 PM on a workday." These are not big problems of society. They're just kind of things that helped me become an adult, learning how to be me. **Jackson** [00:22:26] But often the writing from other people that we all find so useful ends up being kind of shaped like that. **Steph** [00:22:31] Yeah, it's just really basic stuff sometimes. **Jackson** [00:22:35] ## [00:22:35] Asking what can be removed and making incremental progress On the topic of removal, you wrote a piece I liked a lot about when you talked about how removal is often invisible, like people cleaning up a beach. **Steph** [00:22:45] Right. **Jackson** [00:22:46] It made me think of the Steve Jobs idea about how focus isn't about just choosing what to work on. It's about saying no to a thousand good ideas so you can work on the things that are really, really important. **Steph** [00:22:57] Yeah. **Jackson** [00:22:58] How do you say no? I struggle with this in writing, for example, or even in editing podcasts and all the other things I do. In how I spend my time, how do you say no to the good stuff so you can spend your time on the really good stuff, especially as someone who's so prolific? **Steph** [00:23:28] The idea of what can we remove is just a question that is hopefully useful for a group or for yourself when you're working on something. Remind yourself to ask that question: What can I remove? What can we remove? What's not contributing to the thing? Oftentimes, when you're writing an essay or you're building an app or you're working on something, some of the prior first draft stuff ends up sticking and staying into the final thing. So that's one of the things that I like about giving myself a long pause before I publish. Then I can see, oh yeah, that was just this weird old cruft that was there from an early version. You get kind of stuck keeping it around because you're in a flow, and you have a memory of your past self from an hour ago when you started writing this essay. It still makes sense. **Jackson** [00:24:36] You needed it to get there, almost. **Steph** [00:24:37] Yeah, you needed to get there. It's like classic wisdom from writers. I forget, it's like "kill your darlings" or something like that. Having that gap where you come back to something with fresh eyes and you're like, "Oh, that's so obviously unnecessary now." **Jackson** [00:25:03] I was holding on to this an hour ago or a year ago or whatever. **Steph** [00:25:06] Yeah, so part of it is one tool that you have is the ability to just come back to it the next day or a year from now. Is it actually urgent? Maybe you're working on something and you can't -- that's not how it works. You have a job to do. You have to ship something tomorrow. We have this all the time with Obsidian. We're working on a new release of Obsidian every few months. There's always a point every single release where it's like, do we want to add this other feature or bug fixer thing, or do we want to ship what we have? An earlier version of myself, in my younger days, would always choose to make it as good as possible and then ship it. But now I'm always just like, let's ship something and cut everything that we can cut so that it's good enough to ship on this particular day. Once you change your mindset to, "I know that I want to put it out there tomorrow," or in a week or a month, it just forces you to trim anything that's not necessary. So that's another tool. It's another form of constraint. One constraint is a time-based constraint: Just wait a year and see how you feel about it. Another constraint is to tell yourself, "I gotta put it out tomorrow." **Jackson** [00:26:38] Yeah. **Steph** [00:26:38] So therefore, I got to cut everything. That zigzagging between those two ends of the spectrum is actually a very common thing that I do. It's like tacking in how you move against the wind in a boat. **Steph** [00:26:55] If you're trying to go straight against the wind in a boat, you have to basically zigzag your way. So you go all the way 45 degrees left and then you go 45 degrees right, and you're making forward progress, but you're doing it in a zigzag fashion. You're bouncing back and forth between left brain, right brain, long-term, short-term, maximalist, minimalist. **Jackson** [00:27:17] Most of us are stuck in the middle, being pulled on both sides all the time. **Steph** [00:27:21] Yeah. Only, there's this quote from T.S. Eliot, which comes up all the time with my partner, which is: "Only those who are willing to go too far can possibly find out how far one can go." So it's just like, let's remove everything. Let's add everything. Let's just see what happens, for science. And then you realize, actually, half of this stuff was not necessary. So, it kind of depersonalizes your attachment to whatever you're doing. I think that was fundamentally the point about that essay, "What Can We Remove?" We get attached to the things that we can see. But when you come to a pristine beach, you don't know who was there before picking up all the trash. **Jackson** [00:28:13] Right. **Steph** [00:28:14] If you're walking around that beach and you see a piece of trash, you should pick it up so that the next person can enjoy a pristine beach. But they will never know that you were there. They will just enjoy the pristine beach. **Jackson** [00:28:29] Yeah, it's not even that they're not thinking about who cleaned it up. They're probably not even thinking about the fact that it had trash. The reason... Maybe there are other metaphors that are better, sometimes interior design or whatever. It's like, it's actually what's not there that makes the space so great. So it's this subversion or this... Yeah, wow, that's powerful. ## [00:28:49] Building a product and company (Obsidian) with the "constraint" of ideology and principles The last constraint-related idea that I wanted to ask about is something you've written extensively about, which is a highly principled, if not ideological, approach to making software and building a company with Obsidian. I think probably the most famous instance of this that you continue to write about in different forms is "file over app." This idea that we should have plain text usable data in files independent of the tool. I'm curious, just very practically, how does having a philosophically driven approach affect the day-to-day of building? And also, how does it affect you over the long term? Even something as simple as how often we can ship an update and what goes into an update. Is it easier to remove stuff because of the principles? Is it harder to remove stuff? Is it harder to add stuff? **Steph** [00:29:44] There are really two totally separate topics here. One is "file over app," which is really a political statement. I think that this is societally important, civilizationally important. It's a rejection of how big tech and a lot of companies are built in the software ecosystem these days, or have been for a long time. That does then become a constraint within what we do at Obsidian, and we try to respect that constraint. But we wrote a manifesto that is very short, very simple, that has five things that we're focusing on, and those are the constraints that we use. They're pretty simple things: one is we want to stay independent, we want to be 100% user-supported, so all of our funding comes directly from our users. We don't have investors, and we don't want to grow the size of the team. That is just a value that has to do with independence. Part of the reasons for that particular set of values--that's one of them, there's also privacy, there's durability of the files. You can go to obsidian.md/about and you can read the whole thing. A lot of those came from the founders of Obsidian, Shida and Erica, who for some reason were naturally just genius about the values. Other things came from my personal experiences having gone through the process of building companies every possible way you can. I did a Kickstarter campaign, my co-founder went on Shark Tank at one point, we raised money through VC--I've done all the different ways that you can raise money and build companies. I just like the "Ocean's Eleven" model the best. It's just the most fun to have a very small team where you just...I love making stuff myself. I don't really enjoy being a manager. I've done it in the past a lot, but I just want to be designing and coding and writing and interacting with the users directly. That's just what I like. Other people might really enjoy working in a big company or being a manager or other things. It's not a prescription for everyone, it's just the way that we enjoy building Obsidian. And it has a lot of limitations. In the previous company that I ran, Lumi, whenever we had a problem, it was like, "Who can we hire who is an expert on this problem?" We'd go find the best person, hire them, and then empower them to solve this problem. Now, if we have this problem, hiring is off the table. We basically don't hire. We have seven people full-time. We've kind of given ourselves a buffer, like in our internal...it's not listed specifically in the manifesto, but it's an internal limit of 10 to 12 people that we don't want to grow past. Currently, we're seven, seven and a half or something like that, because we have some people working part-time. But if the problem comes up, we have to either figure out how to solve it ourselves, or we just decide it's not a problem we want to solve at all. So, that happens all the time. We can't parallel process on 20 different things at the same time; we can only do one or two things at once. Companies are these amazing, symbiotic, super-intelligent organisms that are capable of doing really complicated things. Amazon has a million people working there, so they can do so many things at the same time. But I don't want to run Amazon. I just want to have fun building stuff. I think having an understanding and shunning this sort of...having an understanding of yourself and being brave enough to just reject this sales pitch that is often given, maybe even a default in certain worlds or contexts, that you have to raise money or you have to do things this or that way. You should just do what feels right to you. It's still possible to be very ambitious within that framework. Obsidian probably...I don't actually know how many users we have, but we probably have three or four million users, and we're seven people. That's pretty crazy. It's definitely possible to do something. **Jackson** [00:34:36] Within that, especially on the ambition note, even the set of constraints and ideals you just talked about, some of them are more political. Some of them are about how you and the co-founders want to live your lives and run the company. Some of them are enabling from a truly principled standpoint. **Steph** [00:34:57] Right. **Jackson** [00:34:58] As an example, I think the "File over App" piece, and particularly digital archival, the idea that our data is actually usable in not only 10 years, but 50 years, 100 years, that is something that is almost mission-driven. **Steph** [00:35:10] Right, right. **Jackson** [00:35:11] How does that balance? Maybe this is a false contradiction, or isn't mutually exclusive. But you can imagine a world where the mission is weakened, or getting to the mission on the timeline or at the scale you hope to is weakened by the fact that you guys don't want to manage people, as an overly simplistic example. **Steph** [00:35:34] Yeah. **Jackson** [00:35:35] And there's a world where, 20 years from now or 50 years from now, the world is different. Maybe I'm assigning too much credit or ambition or whatever, but these are, maybe some of them are more just theoretical, but some of them could actually be very practical things where your core principled constraints end up running up against each other. Maybe you don't need to raise $100 million in venture capital, but having 20 people could help Obsidian get much more materially or much more quickly to its mission. **Steph** [00:36:06] Yeah, so you're saying "File over App" is this big idea that could have more influence in the world if there were more people working on it? **Jackson** [00:36:14] I don't know that, but. **Steph** [00:36:15] No, no, I think that's definitely a fair point. It's probably true to some extent. I think that, I don't know, I would argue that even as seven people building this thing that is kind of an example of what we mean by "File over App," it has had more impact than if we had had a million people working on it. Because what we've seen over the last couple of years is the biggest companies, like Microsoft, just put out basically a new tool that converts all these old file formats like Word and PDF, every kind of file format that is proprietary and not open, to open format markdown. They're doing it, I think, mainly because it's the best way to ingest a whole bunch of data into AI. Yeah, but it was pretty surreal for us. It was cool. And there's, I can think of about 10 different startups that have started based on "File over App." And they're like, "We're doing 'File over App' for accounting. We're doing 'File over App' for this or that." It's almost like a request for startups that YC does. It's just like, "File over..." Sometimes I'll post on social media, "We need a 'File over App' of this category." And then people are like, "Oh, I should go build that." There are people doing CAD "File over App." People are doing video. They're taking that and expanding in other directions. And if we thought of "File over App" as a proprietary idea that only we should be the ones focusing on, it would be less powerful. It's better for everyone to have. If the idea is powerful enough, and enough people agree with it, they can just go take that and run with it and build in their area. Now it becomes like there's a shared ownership of that idea. And I think that's, in a way, more powerful than trying to do it all ourselves. But it requires us to give it away and be communicative about like, "Hey, everyone can do this." **Jackson** [00:38:25] Maybe even more simple than that, or more foundational, might just be that the most important part of anyone's work is staying in the game. On some level, you are doing it in a way that allows you to do it, and maybe. Not to mention, if you were managing a bunch of people, maybe you wouldn't have had time to write "File Over App." **Steph** [00:38:45] I didn't. Back when I was doing Lumi, I didn't have time to write because I was managing people. ## [00:38:52] Using Obsidian makes Steph better at building Obsidian It's funny, I'm still probably one of the top Obsidian users. I use Obsidian all the time, and I love using it. So, if I'm not working on it, I'm using it actively at least an hour a day. But I have it open constantly in the background, so I'm bouncing back and forth. Sometimes I'll just literally spend five, six, eight hours in a single day just writing in there. I write my essays in there. I publish from there. I work on my side projects, like this piano thing we were talking about, a lot of my planning. Or sometimes I'll be building plugins. I think if someone who is a user of Obsidian were looking at the way that I spend my time in a day, they would be like, "You could be spending more of your time building Obsidian instead of using Obsidian." Some people are like, "Where's this bug fix that I've requested two years ago?" Or, "Where's this feature? You're spending too much time using Obsidian and not building Obsidian." That's kind of what people are saying, in a certain way, not in those words necessarily. But I don't think I would be building Obsidian if I wasn't using it. To me, actually, the company is secondary to my personal goals of actually using the tool that I want. The reason I'm making it is so that I can use it, not the other way around. And if I wasn't using it, then Obsidian, the tool, wouldn't be as good as it is. **Jackson** [00:40:19] Yeah, that's a powerful paradox, in a way. **Steph** [00:40:20] And that's something that I didn't enjoy as much working on my previous startup, which was, like, we were a B2B supply chain tool. The thing that we were making, we were not using ourselves. And because we couldn't, we were busy building the software that was like a manufacturing and logistics platform. I think, going back to the earlier topic of building something for yourself, if you really care about that, you have to make sure that it remains true even as the thing grows. It's really hard. It's really hard to keep working on it. Just think about any startup, like, that you use their product. How many of them are actually using the thing that they make all the time? **Jackson** [00:41:02] When they probably started out using it, or they had that problem. I mean, presumably, you guys had that problem with Lumi, and that's what, yeah. The, it's almost a craft in and of itself to set things up in a way and maintain them in a way that allows for you to keep playing the game you want to play. **Steph** [00:41:21] Well, and you have to have the stamina. Again, everything I'm saying is not a prescription. It's just, this is what I enjoy doing. If you enjoy, like, if your whole life is like enjoying making things for others and being in service of others, like, there's amazing entire professions and things that are all about that. And that is amazing. I think that if you're interested in building something that you want to use, and you also imagine yourself doing this for a long time, which is not a prescription whatsoever. Lots of great companies get built, and then they get sold, and then people move on. I often wish that I could, I've often had ideas of writing books or comic books or making movies. And the allure of that is so appealing because, like, you make a movie, it's done, and then you make another movie. You do a new thing, and it's over. **Jackson** [00:42:17] You work on it for three years, but. **Steph** [00:42:19] You work on it for three years, or five years, or ten years, but then you're done with it. That artifact is complete, but software is never complete. It's always evolving. It can't be because there's no firm ground to stand on. The operating system is changing. Everything's changing under your feet. So, if you're someone who really likes that idea of being able to move from one thing to the next, then maybe software is not the right category for you. **Jackson** [00:42:50] It's ironic, given how much faster it is than other mediums, but I think that's right. **Steph** [00:42:54] Yeah. **Jackson** [00:42:55] I was at Sundance this weekend, and there's something you could see -- or maybe I'm projecting, but there's the sense of the filmmakers are doing the Q and A. There is this crazy level of, "Whoa, it's out. It's done." Maybe there's still work to do. But the last five years have all culminated. Software is a totally, if not inverted shape, a very different shape. Theoretically, you could work on Obsidian for 50 more years. **Steph** [00:43:21] Yeah, I guess so. I mean, I think it's weird because I'm pretty sure software is going to be different in a major way. We might not be using computers in the same way that we do today. Certainly many of the -- I don't know if we're going to have JavaScript and CSS and the way that we build apps. The way that we build things may change a lot, or there are so many things that it's so unpredictable. **Jackson** [00:43:54] Well, that's the unique thing about software, too. People were making movies a hundred years ago. It was a little different. **Steph** [00:43:59] People will just be typing with their fingers into a thing 50 years from now. **Jackson** [00:44:02] Or even what is the oldest computer or piece of software that anyone uses? It isn't heavily abstracted. **Steph** [00:44:09] Huh. ## [00:44:10] What makes for good design and seeing the world as something designed (by nature or man) **Jackson** Okay. I want to shift gears a little bit and talk about design. You are -- again, when I said you were prolific earlier, I really enjoy your writing, but I think from a design standpoint, that's kind of more what I meant, just given that when it comes to showing up with a strong point of view in many different forms. Even just chatting with you and hearing more about other things you've spent time on, you bring a design-focused approach and a really strong point of view to most of the ways you show up in the world. As a super basic kind of initial question, what makes for good design? **Steph** [00:44:42] Wow. **Jackson** [00:44:44] And if you want to take a second part on it, what has made you a better designer? **Steph** [00:44:49] Constraints is all is what makes design great. Gosh. This is a topic I've thought a lot about, but I haven't written that much about. And so I feel like my thoughts are not as organized as they could be. The way that -- I thought that I was going to become a biologist when I was going through high school. I really focused my studies on physics, chemistry, and biology and decided I wanted to become a biologist and that I was going to specifically become a zoologist or evolutionary biologist. Then I spent some time, that's what I went to school in college for. Then at some point, I realized I had been doing a lot of artsy stuff on the side. I had been making Winamp skins. I had been painting, photographing things. I kind of dabbled with every medium at some point, just as a hobby. And I realized I kind of discovered design late because I think I was 20 or something. I was in China. I was at a Muji store in Singapore, and I was like, "Wait a minute. Someone has decided what the diameter of this pencil should be." It just sort of dawned on me all of a sudden that people had been making these decisions about all the objects that are around me. **Jackson** [00:46:12] Did creative things become more serious when you thought about it as design? **Steph** [00:46:16] Well, I just had never really thought about design as a profession. I always kind of just had been messing around. I didn't realize that it was people's full-time job to do this kind of thing. This was 2005, I want to say. Suddenly, it was like Neo in the Matrix. I was just looking at everything all around me. I was like, "Whoa, someone made that decision and that decision, and this material, and that diameter." And I was like, "I could do that. I have opinions about what diameter something should be." So then I decided to shift and try to become an industrial designer. I lived in the Netherlands and I worked at an industrial design firm there. I went back to school and studied industrial design. Then I met my good friend, Jesse, who became my co-founder for 13 years across two different companies. We turned the things that we were passionate about in industrial design into software. How do we actually help other people manufacture things? I'm skipping a lot of steps, but all along the way, it was exposure to having this other lens on the world where you look at things first from a biological standpoint. I have the choice to either study what nature has created and surrounds us with, or study what humans have created. The human path seemed more appealing because I could actually contribute something, as opposed to just studying something that was already made. I mean, in theory, I could have gone down the genetics route or something. Maybe there's a hybrid of those two, or like wetware or something like that. But I thought it would be more interesting to kind of apply my own process of natural selection to objects, interfaces, and things like that. **Jackson** [00:48:08] Cool. **Steph** [00:48:09] And then, just by coincidence, when I shifted into design, that's when the iPhone launched. It was just a total game changer in terms of what you could do with UI. The touchscreen was so powerful because it really created that connection between the physical hardware and the software. You could literally make buttons that you can touch in UIs. So that was really exciting and kind of pushed me down that software path. But along the way, I took classes in typography, woodworking, and UI. I studied things just by going to the "view source" or "inspector." I've just always had this curiosity about how things are made, how they look, why they look the way they do, and what the structure of things is. I've had just a lot of curiosity. And then you kind of start to see patterns more. You see patterns in nature, and you're like, "Oh, it's, again, the question of constraints." Like how do, you know, Fibonacci sequence type of stuff. You look at how plants grow and how they work, and they're all working within these constraints. So I don't know if I'm answering your question, but ultimately the things that make a system feel appealing to use, ergonomic, intuitive, understandable, beautiful, they tend to find a way to distill what this thing is for into something that is easy to understand. The things that are easy to understand tend to somehow be simple or understandable. That's the thing that I'm always searching for: how to make something understandable, and what's extraneous, what can be removed. **Jackson** [00:50:13] If you reverse that story, you would have a strong case for why so much of great design is so obvious, intuitive, or even invisible. It's almost the two versions of you: it's the first version of you that just is appreciating the world, and it's the... great design almost puts people back in the Matrix. **Steph** [00:50:36] Yeah. **Steph** [00:50:39] That's true. Ignorance is bliss, as Cypher said. It reminds me of my high school biology professor, shout out to Mr. Billiot. He was the first to teach me the idea of "use it or lose it" in nature. It takes nature millions of years to get rid of something like a tailbone or an appendix. Nature has this way through evolution of shedding unnecessary things and being evolutionarily fit to its environment. So, what is necessary for a product to be fit to its environment? It has to be efficient at what it does. The efficiency, in a way, is what creates beauty. I love looking at machinery because machinery is not trying to be beautiful necessarily, but it becomes beautiful just by the form following the function. The function of the thing needs to do a certain thing, and so it has to look a certain way. Through that, there's a certain kind of beauty that we recognize that is not that different from nature. Maybe I come from a more modernist design tendency, a more minimalistic, less maximalist. I appreciate it when I see it, but I have a really hard time practicing it. If you go to Europe and you go to ancient architecture or the Renaissance, it's so beautiful and so complex and so ornate. I have no ability to do something like that. It's really hard for me to design things that have a decorative aspect to them. I'm not sure if that's just because I was trained in the world around me because I grew up in the era of mass production, and everything is designed to be very streamlined, or if it's natural to... I don't know if it's nature or nurture, the kind of tendency towards minimalism that I have. But I can appreciate the beauty in complex things, but I also am always searching for the most pure version of whatever it is I'm building. ## [00:53:11] What makes a good tool? **Jackson** Well, you've mostly spent a lot of time working on tools, which could be one reason for at least a lot of your design manifesting with an emphasis towards function. **Steph** [00:53:22] Yeah. **Jackson** [00:53:23] What makes a good tool? **Steph** [00:53:26] My favorite definition of a tool is it's something that converts what you can do into what you want to do. A hammer is a perfect example. You have what you want to do, which is put a nail into a wall or a piece of wood or something, and what you have is a hand. You have to convert what your arms can do into a point of hard steel that will just drive that nail into the wall. Once you see tools in that particular way, it opens your eyes to questions like, what is a car? What is a computer? Why is a computer the shape that it is? Why do the keys exist? Because we've got fingers. If we didn't have fingers, a computer would look different. Then you start to look all around you, and everything is made out of handles and ergonomics. That translates just as much in the software world. We have eyes. We can speak. These are the things that we have at our disposal. This is what humans can do. This informs the shape a tool designed for human use should have. The best tools conform to us as much as possible and allow us to do something that we want to do. The edge of tool-making is always, what are some new things that we want to do that we never thought of doing before? What are some new capabilities in the way that we can make tools? For example, right now, AI and LLMs are so fascinating because it's a new substrate for us to create tools that are really interesting. Humans are not very good at reading 7 million books in every language. We're not really that good at that. But we have desires, like we want to make a new piece of software and take all of the knowledge from the internet. Every bug that's ever been reported to Stack Overflow is in an LLM. So you can ride on that giant sandworm and take it into the direction that you want it to go. A tool can be made out of that. But then there's also the needs. A lot of our needs as human beings have not changed at all for thousands of years. We still need a comfortable place to sit, a comfortable utensil to put food into our mouth. These needs haven't changed very much. They are pretty much exactly the same as they've always been. How do we satisfy that need in the fittest way possible, given what we're able to create today? ## [00:56:20] Thinking tools and Obsidian **Jackson** Obviously, in the physical world, that explanation is really easy to apply. In much of digital space and software, we've created all kinds of tools for doing things, creating things, consuming things. You work on a thinking tool. Some people use this phrase, "tools for thought," which I think has some baggage with it. But that hearkens back to this classic "bicycle for the mind" idea around computers. I think people are bringing that up again now with LLMs. But in some sense, it's a little more abstracted than even something like, "Hey, I want to consume a book in a shorter period of time," or "I want to create a video," or whatever, so many of the other things we do with software. In some sense, the ultimate thinking tool, the pen and the notebook, hasn't necessarily evolved that much. I would at least put Obsidian and tools like it in a bucket of, yeah, I use it sort of to store things. But you were describing this earlier, like the most interesting thing about Obsidian is I'm using it to think. **Steph** [00:57:21] Right. **Jackson** [00:57:22] Which feels like it's this more amorphous, or at least if not novel, it's a little different than most of the ways people experience using computers and frankly, most other tools. **Steph** [00:57:33] People have had ways to scribble things onto things for thousands of years. I think that Obsidian doesn't necessarily have to do anything fancier than that to be useful. Our needs haven't necessarily changed. The question that I ask myself is, how can Obsidian allow you to think about things in a way that you could not through pen and paper? One of the things that is really core to Obsidian is just that notion of a link, which has been around for decades. That's how Wikipedia works. You can go down a rabbit hole. What if you could create your own rabbit holes? It's really hard to do that with pen and paper because the just notion of clicking on a link on paper, if you've ever read a book that has a lot of footnotes or references, flipping pages is not a very, it doesn't work really well. **Jackson** [00:58:40] It's especially hard to be in a flow. **Steph** [00:58:44] The ergonomics of that just slow you down. It's just slow, and your brain can move so much faster. So I think the most important thing about Obsidian is just being able to click links and connect things with links. It's that simple. All of the extra stuff, everything else is on top of that foundation of just being able to link an idea to another idea. Then I think what, you know, Erica came up with around the plugin architecture is genius because it allows the core of the app to stay relatively simple. We have millions of users. Every user has a different set of plugins. The multiplication of that is just, there's more different configurations of Obsidian in the world than atoms in the universe or something like that. The way that people use Obsidian is so different from one person to the next. And so that plugin architecture allows for that without us having to build a zillion features. It's also how we're able to stay small, because we rely a lot on the community to build all those different other extensions on top of the tool and what, and the way other people's brains function. I do think we're kind of in a moment in time right now where we're starting to discover more about neurodiversity and understanding that, hey, I have synesthesia, I have aphantasia. The way my brain works is probably different from yours and different from somebody else's. I can use, Obsidian is about malleability. It's about shaping the tool around your brain rather than the other way around. A lot of tools ask you to shape your brain around it. It's weird because it's like, we're very opinionated about the fact that it should be so unopinionated. We're very opinionated about the fact that you have to be able to customize every aspect of it because your brain is going to be different. Maybe your brain is going to be different from someone else's brain, but it also might be different from your brain a year ago. You're evolving to learn new things. In my own use of Obsidian, my use of it has grown a lot in complexity over time because I started to feel more comfortable with different ideas. There's this idea called Evergreen Notes that I think Adam Matuschak was the person who came up with that term, and I wrote a piece on it, an essay about that, which is just kind of forming a meme for yourself of an idea inside of your notes. So you take a whole concept and you somehow distill it to a short phrase or word that allows you to build on it. And that's something that's really, you know, it's possible to do in book form, but it's really nice to have this set of Legos that you can play with, where you take a whole concept. That's what's powerful about memes or jokes or inside jokes that you have with friends or something like that. You can just say one word, and. **Jackson** [01:01:53] Like, suddenly so much information is packed inside of that. **Steph** [01:01:56] Yes, so much. And so you can create those memes just for yourself inside of Obsidian. The meme can, of course, be something funny or powerful in some way, but it can also just be a shortcut to a group of ideas that only you've had. A lot of people in the Obsidian community like to do world building. They're playing RPG games, they're writing books, they're creating their own little universes for various purposes. They are coming up with ideas that are completely native to that universe that they're creating, which doesn't make sense to anybody else. **Jackson** [01:02:28] It's like a whole bunch of **Steph**topher Alexander little pattern worlds. **Steph** [01:02:31] Yeah, and so that concept maybe allows you to have some more complex thoughts because you're able to more quickly take a whole concept, mix it with this other concept, and now form a bigger concept out of those. What can the tool give you? Enough of those basic building blocks so that you can take your thinking anywhere you like? **Jackson** [01:02:59] Right. Yeah, it seems it's this beautiful idea. In practice, building a tool that is ergonomic enough, affordant enough, and simple enough for anyone to get started on, almost like the beginning first level of a video game, that can then go as wide and as rich and as complex. This tool is probably like one of the hardest design problems conceivable. **Steph** [01:03:24] Yeah, and I think we're not making Obsidian intuitive enough for newbies. I think that's something that we still have a lot of work to do on, making it the first level of the video game more... **Jackson** [01:03:40] It's a Ferrari engine that you can bolt things on top of. **Steph** [01:03:43] Yeah, make it easier to adopt at the early stage. Then, the infinite depth is always going to be there because of the plugin architecture. **Jackson** [01:03:52] Also, alarms and software are going to be easier to create. **Steph** [01:03:55] Exactly. Yeah, you might be able to. We're getting to a place now where you might be able to create a plugin just for yourself. Probably in the next year, there'll be a really good way for you to just make a plugin. It's just for you, and it does whatever the task is. **Jackson** [01:04:13] Computer, can you help me? I want to be able to do this. Okay. **Steph** [01:04:16] Yeah, and that's really cool. But we also have to be able to take someone who's completely new to this idea of this kind of tool and do a little bit of hand holding in the beginning. So that's definitely an area that I'm thinking about a lot. ## [01:04:32] "In good hands" and caring more than anyone else **Jackson** One of my favorite things you've ever written is a post called In Good Hands, which is maybe the coolest way to frame. Maybe I wouldn't have always put it in the design bucket, although obviously, I think there's a lot of design inside it. And it's this idea of omakase. It's like, hey, trust me. Give me a little bit of freedom here, or trust here, to take you somewhere. In many ways, I think it describes at the very least the essence of what I experience good design to be, which is this again, it's almost becoming invisible. And I'm not having to worry about all the details and all these little things. With that in mind, as maybe an overarching principle, obviously it could apply to a specific experience or serving someone tea, but I think it could also apply to building products or designing products. How do you implicitly communicate that kind of care or that kind of trust? **Steph** [01:05:25] Yeah. Well, when I that was one of the essays that just came out all at once really quickly. It's a little different from most of my essays because it's written from the perspective of the consumer. This is what I look for. It's not a prescription of what to do. It's please, world, feed me these kinds of things. **Jackson** [01:05:48] Yeah, yeah. **Steph** [01:05:49] And it is a feeling that everyone has recognized. You watch a movie or you go to a restaurant, you sit down, and like a minute in, you're like, "This is gonna be a good movie. I can tell already." I know. Whether you have the vocabulary to express it or not, if you haven't been to film school or whatever, you may not know, but you feel the way that it's shot, the way the acting is, the attention to detail is coming together in a way that makes you feel like the person who made this, or the people who made this, really cared. **Jackson** [01:06:27] At its best, it's non-verbal. It's like, I actually can't describe what makes this so great. **Steph** [01:06:31] Yeah, exactly. And I think almost by definition, anyone who's listening to this is probably going to be trying to make things in this particular way. But where it doesn't happen is often times in this factory environment. If you work at a large company and you're tasked with solving this particular thing, you're in a factory that makes products, that invents new things. So your project is to grow the number of users or improve the retention or whatever. And that's probably not going to lead towards a thing that makes you feel in good hands. When I think about the movies that I love, not a lot of them come from that factory style of heavy recipe, of making big, you know, Marvel movies or something like that. Maybe some of those early MCU movies were kind of in good hands because you felt like there's some people who are real comic book nerds who were so passionate because they'd been reading the comics their whole life and they wanted to make a really great comic book movie. But then once it had been turned into a formula, you kind of start to lose that feeling. And so fundamentally, I think the best way is to really care. To just, if you and you can feel yourself as the creator, stop caring about things sometimes. And that's a very hard feeling. **Jackson** [01:08:05] Yeah. Oh man. **Steph** [01:08:07] And when you stop caring about something, there's no chance that you're gonna make something that makes someone feel anything. **Jackson** [01:08:12] That's falling out of love in a way. **Steph** [01:08:14] Yeah. If you're not in love with the thing that you're making, how is anyone gonna love it? So it's hard to fake that. You have to be patient and choose things that you want to work on, that you really have the attention span and curiosity to put that amount of attention to detail because you care so much about it, because you would want that thing to be that particular way. And then the decisions that you make don't really make sense from an allocation of resources standpoint. It doesn't make financial sense. It doesn't make sense for you to be spending so much time obsessing about this particular detail. But you have to in your soul because you know that it would give you pleasure if you were on the other side of that. **Jackson** [01:09:07] You're painting the back of the cabinet. **Steph** [01:09:09] Yeah. **Jackson** [01:09:10] You know it's there. **Steph** [01:09:11] You wouldn't be able to sleep at night if you knew that the back of the cabinet was not completed. So I don't know how to find that, really. I don't know how to tell someone to do that. And maybe the thing that you're doing is not going to be a huge commercial success because the thing that you really care about and are super geeky and have infinite patience and attention to detail for is not necessarily something that a million other people care about. And so that can be hard to hear sometimes. **Jackson** [01:09:48] That's a little bit of the advice to create for yourself, right? Maybe it won't, but also the world's pretty big, and the internet's pretty big. It turns out that if you really love it, **Jackson** [01:09:58] Maybe part of this is that the love has to come first. Then you can't necessarily control how wide that reach might be. **Steph** [01:10:06] If you care -- the recipe for success in almost anything is to just care more than someone else. In my experience, that's my way of going about it. There are other ways. You can make it cheaper, you can make it at bigger scale. There are a lot of other ways to be successful, but my favorite way of building things is just to care the most out of anybody. I know that I can really care about all the details of this particular thing. And then, okay, you can care a lot, but then you have to have the craftsmanship. You see, again, movies are a great example. You can see great filmmakers evolve over their career and see, like, if you go to old Ghibli films and you go to the newest Ghibli film, you can see how Miyazaki -- the detail work is so much better. The way that they're using color, the animation is so much smoother. They have more time to be able to spend on all these details. You can see the vision that he might have had earlier in his career come to fruition. Your earlier attempts may not have the same level of craftsmanship because you're still learning the technical skill to be able to accomplish your vision. **Jackson** [01:11:24] Yeah. **Steph** [01:11:25] And that is also frustrating because sometimes you're like, "Man, I really wish I could do this." For example, I'm learning how to play piano, and I suck at it. I've been working on it for a little over a year. My partner is an amazing pianist. She's literally a genius. She started playing piano when she was four years old, and she's just brilliant. I can see how frustrating it can be for her to teach me these really basic things, but she's also a great teacher. The stuff that she was doing at four years old, I'm struggling with right now. It's so frustrating because I have aphantasia, which means I can't see pictures in my mind visually, but for some reason, I can hear music extremely well. It's like I'm listening to an iPod or something in my head. If I just want to play a song, I can just play it. Close my eyes, I'm listening to a whole song, it's great. But I can't see images for whatever reason. I have music in my head, and I want to be able to express it, but I can't. My fingers will not do the things that I can think of. **Jackson** [01:12:37] You don't have the interface. **Steph** [01:12:38] Yeah, and I can whistle, I can hum -- I'm not a great singer. I'm at that place. But I feel like I've been having a bit of a breakthrough in the past few months where I'm starting to use a different skill set, which I have, which is making products and tools. I'm trying to use that skill set to train myself, to create my own approach to learning that is going to work for me. I've tried every app that's out there, and it's not working for me. I have a great teacher at home, but she's not full-time. **Jackson** [01:13:16] She also can't see totally inside your brain. **Steph** [01:13:18] Yeah, and so I'm trying to kind of get to this place where eventually, I'd like to be able to recreate the music that's in my head and play it on a piano. **Jackson** [01:13:30] Sounds like a bicycle for the mind, by the way. **Steph** [01:13:32] Yeah, it's a -- I don't know what it is for the mind, but it's a thing for my mind. **Jackson** [01:13:38] Well, the whole thing about the bicycle is like, it turns the human from one of the least locomotive -- **Jackson** [01:13:44] The example you just gave expresses what is so wonderful about design in general and tools, but also what excites me so much about where technology might go. There's this Ira Glass quote about when your taste and your abilities don't line up. This was maybe inspired by games, but there's this really empowering idea from this guy, C.T. Nguyen. He talks about how game designers sculpt agency by aligning the player's goals and their abilities. **Steph** [01:14:21] Yes. **Jackson** [01:14:22] How many people have had the experience that you described with piano in countless ways? We've made tools, somewhat. The internet and software and technology are really powerful. They've done a lot of cool things. But maybe the surface area of allowing us to have more agency in all kinds of ways, to do things we haven't maybe been able to do or haven't even considered trying. **Steph** [01:14:47] Right. **Jackson** [01:14:48] Especially when software is free and really fast to make. That feels like such an amazing opportunity and kind of unlock, and huge. To allow a person the ability, maybe the dream would be that you can sit down at a piano and have the same comfort that your partner does. Despite the natural affordances of the piano not meeting you where you were, at least initially, and not having that history. That feels like a dream. **Steph** [01:15:22] In the Matrix, they have this technology where they can just download knowledge into your brain, and you're like, "I know piano." And you suddenly, I'm like, just like, that happens. I'm just imagining a future where that exists. Or there's an, you know, and, like, somehow my brain gets downloaded with piano knowledge. Or there's another universe where, instead of my brain becoming, you know, downloading all how to be a concert pianist, the piano downloads my brain. And it's like the piano is like, "Oh, I can see your thoughts now. I can hear the music that you can hear." That's another world. But then probably neither of those things is going to happen. What's going to happen is another essay, which is "Pain as Information." Which is like, the pain of having to go through learning anything is painful. I mean pain in a very vague or broad sense. It requires work, and it requires you to reshape your brain. And so I'm going through that process right now. But I know that I have enough stamina for this particular problem, like piano. I care enough about piano that I know, even if it takes me 10 years to get to the place where I can do what I'm imagining right now, I have enough stamina that I'm willing to power through that pain. And that is something that, again, it's like, do you care enough about this that you're going to go through the pain of becoming a craftsperson in whatever it is that you want to give the feeling of being in good hands to someone? **Jackson** [01:17:09] Yes. **Steph** [01:17:09] And that's. **Jackson** [01:17:10] That's what being a designer is on some level, right? **Steph** [01:17:13] Yeah, but everyone's a designer. I'm like ratatouille on this. It's like, you know, everyone can be a chef. **Jackson** [01:17:19] I guess my point would be, I agree. It's just that most people aren't going to take it quite as far in their willingness to design their life around them to get to what they want. Their willingness. You know what else is interesting is I love what you said about just caring more. In some sense, that's a beautiful other side of the coin of this pain point, which is to say, when you care more, sometimes you're willing to go through more pain. In fact, that's what allows you to go through more pain, to get through more information and eventually get to the point where the pain isn't there and you can do it. **Steph** [01:17:55] Once you accept that learning anything is going to have pain, then the pain becomes less bad because you're like, "Oh, pain. I'm learning." If you associate pain with learning, then you can also see when you're having pain that is just repetitive. You're literally banging your head against the wall or you're putting yourself through something. Not all pain is good. If you keep having the same situation happening to you over and over, you need to experience new pains. You need to go. Even though I feel so far away from my goal when it comes to piano, I do see that I'm a million times better than I was a year ago. There are certain things that I understand now about piano and playing and following along to songs, playing by ear. There are so many things, both in terms of just the vocabulary of it and the muscle memory, so many details where I'm so much better than I was a year ago. That makes me feel like, okay, I know that I can keep working on this and I care enough about it that it's worthwhile for me. So I think maybe that's the thing to emphasize. If you're trying to make something that will elicit that feeling, you have to keep working on the craftsmanship of it. In order to get to the place where it's really going to feel that way, you have to have enough curiosity or passion to keep going. **Jackson** [01:19:24] Are there any all-time or just recent experiences or tools or products that you either just really admire from a design standpoint or that specifically have kind of given you that feeling of being in good hands? **Steph** [01:19:40] I was just thinking about some of my favorite experiences from last year. Some of my favorite movies: I really liked *Perfect Days*. **Jackson** [01:19:49] I love that movie. **Steph** [01:19:49] That was a great movie. I really liked *Challengers*. I thought the music was so amazing. **Jackson** [01:19:56] Those two are really quite a pair of features. **Steph** [01:19:58] I know, very different. I liked *Tampopo*. **Jackson** [01:20:03] I just watched that last year, too. **Steph** [01:20:04] *Tampopo* instantly shot up to my top five favorite movies of all time. And *Tampopo* is kind of about being in good hands. It's this 1985 movie about this lady who wants to have a really good ramen shop. It's so goofy. The actors in it are all like, it's like a superstar cast from these Japanese, it's a Japanese movie. It's so good. And then I had a lot of great sushi in the past year. There are a few omakase places. I really took the omakase thing seriously, and I was like, I gotta find some really good. You know, an acquaintance of mine started a Michelin star sushi place, and that kind of put me down this path of exploring other interesting sushi places. Literally to the point where the next project I'm working on is basically building a sushi restaurant inside of my house. **Jackson** [01:21:06] Of course you are. **Steph** [01:21:07] Because I love cooking for people, and so I want to cook in omakase style for my friends and make them feel in good hands from that perspective. That goes into a whole other side of it. **Jackson** [01:21:21] Have you ever had anything where you're like, "Ah, I probably couldn't do that."? **Steph** [01:21:25] Oh, yeah, all the time. **Jackson** [01:21:27] Because from the outside it sort of just seems like you don't have enough, like there's infinite possibility, it's just there's not enough time. **Steph** [01:21:33] That's also true, but the two are not mutually exclusive. ## [01:21:41] Engaging all five senses I really like when all the senses can be engaged in an experience. Restaurants are great for that, and movies to some extent, although smell and taste are not usually as evoked in that medium. But it's why on my website there are essays, recipes, everything. I'm working on the music side, the color. I've got my color scheme, website sound effects. Basically, where I'm projecting 20 or 30 years from now is that all these things are interacting with each other. There's touch, taste, sound, sight, and somehow mind is in there too. All these things are intersecting with each other, and it's really synesthetic. How do I let other people see the world the way I see it in this very synesthetic way? I can't think of something more fun than that. It's so fun. There's not really a medium for that, that I can think of, aside from software and restaurants and homes. Connecting all these different things to each other. But the fun of it to me is, how can we make these things cohesive with each other? **Jackson** [01:23:01] Totally. Maybe some Neuralink type things in there too. What I love so much about that is, one of the patterns of my life the last year has just been, I find myself increasingly pursuing and chasing quality of attention. Increasingly feeling like attention is the only thing, and I want deeper attention, whether that be how present I am or how long I'm doing one thing. It seems that engaging multiple senses, especially engaging all the senses, is a really great path or proxy to that. **Steph** [01:23:37] And this is why, when you see a really great creator that you love, you're like, "I would love... What would it be like if **Steph**topher Nolan had a restaurant?" How would it work? And now that we have these AI tools, you see, like, what if this film director made this other property? Like a Wes Anderson or something. There's the, let's take style transfer between movies or something. **Jackson** [01:24:12] Or a Studio Ghibli Pokemon. **Steph** [01:24:14] Yeah, there was Star Wars like Wes Anderson. And that's so fascinating of an idea that maybe we could get there at some point where I just want to go inside of some different people's brains and see what it feels like to be completely enveloped by that person. **Jackson** [01:24:33] That is a great way to describe how you, at least, are starting to show up online. It's really cool. It is starting to become more of a world, so I'm excited to see it in 20 years. ## [01:24:46] Creating cohesion or your own cinematic universe **Steph** Oh God. **Jackson** [01:24:47] Yeah. **Steph** [01:24:48] But that is... I forget who said this. Someone had a good essay about this that was like, basically everyone should be creating their own cinematic universe. It's like, what is the **Jackson** Cinematic Universe? What does it feel like? I had this unwritten draft of an essay, which was back in my Lumi days. I felt that my title was Chief Cohesion Officer or Cohesiveness Officer. It was like, what is... I feel like sometimes companies need that person, which is kind of the role of the CEO, but it could be also a taste thing. You're the chief cohesiveness officer of your life and of your output as a human being. **Jackson** [01:25:34] Yes. **Steph** [01:25:35] Your job is to make these things kind of feel harmonious across the different mediums that you're working in. **Jackson** [01:25:45] You're choosing to use your language. You're choosing, with relatively scarce resources, at least in terms of time, which things you're going to really care about. And then, by the way, being able to do that and bring them together, that's an amazing, really empowering blueprint for creativity, I think. **Steph** [01:26:06] Last year I had two experiences, one shortly after another. One was seeing the French band Justice. I don't know if you know them. They have a really incredible live experience. **Jackson** [01:26:20] Yeah. **Steph** [01:26:21] And then the other one was an exhibit by this Icelandic artist called Olafur Eliasson. He does installations that have a lot to do with prisms, mirrors, and colors. Large-scale installations. The Justice thing is so cool because they've been following in the mold of Daft Punk in terms of how they release albums. So they'll release one album, and then they do the live version. For the first one, it's just remixing their first album. But then the second one, it's like, take the first two albums and mash them up together. Then they created a third album, and then they did their live album, which is a mashup of the three previous albums. Now they're on to their fourth or fifth, I forget. I think they've released four studio albums. So their latest show is: how do we mash up these four albums? Everything is an ingredient in this mega soup. If you're someone who knows all four albums really well, it's kind of mind-blowing because you're like, "Oh, my God, they're taking the beat from this song and putting the lyrics from that song, and then the melody is from a third song." You're experiencing this, and it's like, "Wow, I'm really inside of the brain of these two guys." On top of that, they're doing a lot of amazing light show visuals. **Jackson** [01:27:40] I went to the one in New York. The visuals were unbelievable. **Steph** [01:27:43] It really made me feel like another way to do what we're talking about is to keep giving yourself future ingredients for future remixes of your thing that you're making right now. If you think of the thing that you're making right now as a future ingredient, then it also tends to push you towards simplicity of the ingredient. You want the ingredient to be useful for remixing. For example, the color palette that I created for myself is like, here's a red color that I like, and it goes well with this blue and this green. Later, I'm going to make a piano thing, and I'm going to reuse those colors. It informs how much composability--composability is like a word from software where you want to make each piece functional and useful when combined with other pieces. That composability is one of the best ways to think about creating more complex experiences over time. The Olafur Eliasson exhibit was a similar thing. He's done a lot of work with prisms and mirrors and different things. You can see in his work the evolution of his--it's kind of hard to describe, but it's like large-scale kaleidoscopes, large-scale mirror installations. You can see how the pieces are interchangeable and modular. He is living inside of this palette of materials that he can work with, which is like mirrors and lenses and colors. I think that's another way to go about doing what we're talking about. You can do that with anything, like words. So we were talking about memes. Your own self-memes are future ingredients for yourself to have thoughts that you can compose together, flavors, ingredients that you like to work with in the kitchen, sounds. It could really be anything, could be an ingredient into something that you'll make in the future. **Jackson** [01:29:55] Yeah, they're little bridges across that whole arena of selves. **Steph** [01:29:58] Yeah, exactly. **Jackson** [01:30:00] And it provides the coherence that-- **Steph** [01:30:02] The cohesiveness. **Jackson** [01:30:03] The cohesiveness, exactly. That so many people are--it's always interesting. Someone who's spent lots of time zigzagging, I have my own relationship to through lines. People always struggle to understand where you've gone before and where you will go. I love the just example too, because it's the way to have the old and the new, especially in music. Such a classic example: "Oh, I like the new album," or, "the old album, why aren't they doing the old stuff?" It's like, I'm giving you a little bit of a reference to where you were and where you wanted, but I'm also going to take you where I want to take you. And there's connectivity there. ## [01:30:44] How to time travel **Steph** I've been working on this essay for a long time. It's one of these that's in the draft state. I'm going to have to come back to it in five years. I haven't figured out what the title is, but it's something like "How to Time Travel." It's basically instructions for how to time travel because one of the most powerful things that you can do, I think, is create milestones for your future self to be able to go back in time to. Creating those sense memories for me is a really useful way of doing it: places and flavors and sounds. The reason those come up for me is because I enjoy having a certain type of sensory experience in a specific place with a specific person. So that in the future, I can recreate that just by bringing those flavors back into the thing, and then I'm back at that place. I can go back in time to a place just by combining those feelings with each other. It's still in this nebulous state, this essay, but it's about controlling the grain of your life, the texture of your life, so that you can, by planting these milestones, speed up time, slow down time, go back in time, just by the way that you plant these sensory markers in your life. **Jackson** [01:32:10] I suspect if we are able to make real progress on time travel in the way you're describing more broadly, it will involve all of the senses to your earlier point. **Steph** [01:32:20] My method of time travel is not like getting into a time machine, it's more like getting a time machine into your mind. **Jackson** [01:32:28] Sure, but obviously people have researched how the olfactory, the smells, but if I really wanted to immerse myself in the memory of an experience, at the very least, I would not just visualize it. I would not just have the sounds. And maybe the point is that the more you stack senses, the more immersion you have. **Steph** [01:32:48] For sure. I don't know if at some point we're going to neuralink this thing and it's just going to plug in and you'll be able to go wherever you want. But yeah, there is something about that multi-sensory power as a way to anchor time and space. ## [01:33:08] Designing for digital durability or permanence & "File over app" **Jackson** Okay, changing gears a little bit, but on the note of time, we talked about file over app. One of your more important ideas that we briefly touched on is this notion that most software and most of the information we collect today is ephemeral or at least likely to be ephemeral. Obviously, the world has a rich history of archival, and then we also have a rich history of losing things. But in theory, much of human culture and society is encoded from hieroglyphs to books and architecture, all these things. And yet now we're having this digital existence, we have very little digital permanence. A couple of ideas I wanted to read of yours that I think convey this well. One is: the ideas hieroglyphs convey are far more important than the type of chisel that we use to carve them. To read something written on paper, all you need is eyeballs. Finally, if you want your writing to still be readable on a computer from the 2060s or the 2160s, it's important that your notes can be read on a computer from the 1960s. So, obviously one empowering idea here is this notion of tools that use Lindy formats, file over app, plain text, whatever. Are there other ways you can design for digital durability or for digital permanence or even products or tools that could become more self-sustaining or repairing? **Steph** [01:34:32] The Lindy effect definitely rules in this respect. The older the format, the more likely it is to still be around in the future. If you want to have more permanence, then use a format that has been in use for a long time and is still in use today. Then you're maximizing the chance. I had this thought before I started working on Obsidian full-time. I was thinking it would be a fun hardware project to make a computer that can last for a thousand years. What if you could make a hardware device that was robust enough in every respect, in terms of the types of materials that you would use, that the connections wouldn't get dilapidated over time? This could literally be an artifact that someone could dig up out of the ground in a thousand years and make some sense of. **Jackson** [01:35:37] One-year-old iPhone. **Steph** [01:35:37] Yeah, it wouldn't have a lightning port on it, probably. How would you get data in and out of the thing? Would it have some other port? It started raising all kinds of interesting questions about what the timeframe is that we could possibly think about here. Or is this all not relevant, and we should just use analog formats for our most important stuff? Is it still useful to print things out on paper, or some other medium, if you really want to preserve it? Not everything deserves to be preserved for a thousand years. I have like a hundred thousand photos on my iPhone. Nobody cares about 99.999% of them. I think that question is a little hard to answer in the present time. What of what we are seeing right now deserves to still be around a thousand years from now? It's a very difficult question to answer because we don't know what the world will be like at that time. **Jackson** [01:36:49] What about even 15 years from now? **Steph** [01:36:51] The predominant way that things are stored currently is in the cloud, in a database, on a service that you have no direct access to. You're relying on those providers to still be around, and you have to have an internet connection to be able to access those services. So if you lose your internet connection for whatever reason, or you're on a flight or something like that, do you still have access to that data? Who controls that data? Can they train their LLMs on it? What kind of privacy do you have? Who else can read it? Is it securely encrypted? All those types of questions come about, and a lot of that has to do with the types of apps that you're using. The software ecosystem is really geared towards selling back access to your own data. You're feeding a service data, and then it's selling you access to that data that you fed into it. We have sort of accepted that that is the deal, but it doesn't have to be that way. That's what Obsidian is trying to prove in terms of giving you control over your own data and making sure that any data that is being synced between your devices is always completely encrypted in such a way that it's private to you. We can't read it, we can't train on it, we can't do anything. It's your data. Obsidian doesn't store things in a big database in the cloud. It is all stored on your devices, across multiple devices, and we just facilitate syncing the data between those devices. You can apply that idea to any other kind of medium of information that you're trying to preserve over time. If Obsidian goes out of business, if the tool becomes not useful for you for some reason, you don't want to use Obsidian anymore, you still have your data. If somehow the app gets deleted off your machine, all your data is still there. It's always in your control. **Jackson** [01:39:12] Yeah, it's the inverted relationship. To your point about selling back the data, most products or apps we use are portals to our information. It should be the inverse. It should be, "I have my information, now let me decide what I want to do with it." **Steph** [01:39:28] We're just not living in that world broadly. But when we see, there's a great book, *Tools for Conviviality* by Ivan Illich, that I would definitely recommend. Everyone who's listening to this, read that. I think it explains this problem really well. We live in a time where there are six or seven huge corporations that control all of software. It's possible, especially with how easy it is to create software now, to have a more homegrown approach. I talk about this in a different essay, "Quality Software Deserves Your Hard-Earned Cash." What is the difference between a jar of mass-produced jelly filled with corn syrup that you buy at the grocery store, and one that you make at home or that you buy at the farmer's market from someone who really cares? When you're buying from Apple, Microsoft, Google, or Facebook, you're buying industrial-scale software that is loaded with high fructose corn syrup. It's loaded with privacy-invasive trackers. It's loaded with proprietary file formats. It is trying to make things at a large scale, at the cheapest possible price to maximize profit margins, and it's not designed to be caring for you as a human being. Because it's now possible to make... Obsidian, we could not be a seven-person company without the toolset that exists today. There's been so much work over the past 30 years getting us to the point where a seven-person company can serve millions of people. But it's almost like the world hasn't caught up to the fact that that's possible now. That's very empowering to startups, to people who want to make a new tool. It should also be very empowering to individual people, consumers, users, whatever you want to call yourself. Those options are now available to you, and they're getting really good. So you have the choice of using those tools that are designed with more care and more principles. **Jackson** [01:41:50] It's a good explanation of why that healthcare or food analogy you use hasn't necessarily materialized in the digital space yet. It would just be really hard to actually make handmade jam equivalently. The other interesting idea that comes out of this is wabi-sabi. It's an idea I really love too. It captures both imperfection and repair, as well as ephemerality. The other downstream effect of this would be that you actually could have software that, maybe to the point we talked about earlier, you patch and mod and tweak because you have the ability to, or because it's really cheap or fast. **Steph** [01:42:34] Right. **Jackson** [01:42:35] That is a little more DIY. At least to me, that could be one reason why people, or even speaking of ephemerality, like the notion of spinning up a piece of software for a job that only you are going to do, let alone a job that only you are going to do once. **Steph** [01:42:53] Right. **Jackson** [01:42:53] That would have been previously inconceivable, but maybe we are entering that world. Obsidian feels like a pretty cool... In order for that to be maximally useful, I think you would want a foundation of a tool like Obsidian, rather than, similar to, I don't know, if you never cook, it's not that interesting to use homemade or organically sourced, high-quality, high-care goods. You might as well go to the fast food restaurant anyway. And so, it's almost like a divergence. **Steph** [01:43:23] Sometimes when I talk about these things, I feel like I'm just shouting into the ether and nobody cares. For example, in the past, we had cars that were serviceable. Anyone could open the hood of a car, look at the carburetor, and literally unscrew every part. Now we have these factory-produced assemblies that are getting simpler and simpler over time, less and less repairable. But maybe they're cheaper to buy. It's much less expensive if you can buy a mass-produced thing that works well and is reliable. That also exists. It's not a Luddite mindset. It's not like we should reject everything that is. We shouldn't try necessarily to be completely self-sufficient. There's a purpose to society, there's a purpose to having specialization. The intent is not to say you should be completely self-sufficient, and everything you use should be ground up, artisanal, mom-and-pop. But there's something where I think we've come to a place where the entire big tech ecosystem is driving towards confusing people into thinking that things should be free. You're overlooking the fact that the reason they're free is because... Why are these products free if Google is worth $2 trillion? Where does that revenue come from? **Jackson** [01:45:12] Also, why is McDonald's cheaper than healthier food? **Steph** [01:45:15] Exactly. So, I think that for some reason, even though tools like software provide a lot of value in your life—the amount of time it might save you doing a particular task might be worth tens or hundreds of hours—we still feel very uncomfortable about spending more than $2 on an app. Why is that? I don't know exactly why. **Jackson** [01:45:41] There's some kind of digital-physical physics thing that I think is partially people getting over. But yeah, it goes back to this notion of a change in disposition to this stuff. Part of it for a while was that the only way to have really good software at scale for a low cost or for free would be to have some of these more traditional bigger models. ## [01:46:05] "Don't delegate understanding" You started to get at something that I'd love to talk more about because I think it's one of the most timely and important things you've written about, which is a post you wrote called "Don't Delegate Understanding." I'd like to read just an excerpt of that that I think is helpful for the audience. I think it's the intro. You say, "There is a parasite. I see it everywhere. It consumes your health and wealth. It preys on ignorance and is easy to catch. It's so common you may not even notice you have it. The parasite has a simple and attractive proposition: Let me take care of this hard thing for you. Trust me, I know better. Instead of understanding it yourself, you choose to give the parasite control over your health, education, money, housing, business, identity, data, infrastructure, climate, justice, even your beliefs." And then there's—I thought it would be interesting to include a paragraph from the oldest blog post on your website, which is called "Chaos Agents," that I think, interestingly enough, you were on a similar theme 15, 13 years ago. You wrote, "A world where knowledge is captured and categorized, interpreted by the masses almost instantaneously, digested, regurgitated, masticated, ruminated, and immediately available to access, pre-chewed." So I think you're getting at the dominant intellectual epidemic of our time: this world of tribalism, socialized truth, fast information. There's this book called *Non-Things* by Byung-Chul Han, and he has this line where he's like, "We don't have time to linger anymore." There are maybe people out there who would push back on aspects of this, and I would encourage people to read your full post. But I think most people hear this and would agree. They would agree both that you're right, but also would agree that it's happening to them. And so maybe my question would be, how do you fight back? How do you find the time? How do you actually block out the noise and seek signal? How do you even have the energy for it? I think most people's experience is not that they don't believe you or even that they're totally ignorant to this, although maybe it's partly that. It's just that there's so much, and there's so much to do. And by the way, Google software is cheap or is free, and McDonald's is cheap. So I'm curious, maybe just personally, but hopefully it generalizes in some way. How do you start to push back against this parasite, as you call it? **Steph** [01:48:49] Well, last year I bought a house for the first time, and that was such an enlightening experience on this because there are so many points in the process of buying a house and owning a house where there are so many parasites. It's like every aspect of it. I feel like this is probably one of the few essays that has a very negative tone. I try not to write in a negative way, but I feel like I must have been upset about something that made me write it in that particular way. Even hearing you read it back, I was like, "Man, that is very negative." **Jackson** [01:49:25] But I don't think it's off, though. I don't think it's wrong. **Steph** [01:49:27] Whether you own or rent, you face situations where there's a leak in your roof, your drain is backed up, or your electrical system has a problem. These were all real problems that happened to me in the last year. You run into all of these issues because a house is a living system. It has power coming into it, it has gas, it has electricity, it has water, and all of these things can go wrong. When you face that problem, unless you have experience with this, you're trusting an expert to come and take a look at the problem. They'll tell you, "Well, I've been an electrician for 20 years and here's the problem." **Jackson** [01:50:22] Or, by the way, you're probably saying, "Hey landlord, I'm not even going to think about the specificity of the problem. Can you solve it? Make it go away?" **Steph** [01:50:27] Yeah, and in the moment, the thing is, you're trying to solve a problem which is, "My furnace is broken and I'm cold. I need heat in the place." You're back down to level one of Maslow's pyramid. So, a person comes and looks at your furnace or your HVAC system or whatever and is like, "Well, here's the problem, the coil or whatever." Oftentimes they won't even go into the explanation. They'll just sort of give you a high-level overview and then they'll be like, "Okay, it's $500 or something." One thing that I try to do whenever that happens is spend time with those people and watch them work. I'm actually curious. I want to know how this stuff works. I want to understand how -- like I have a furnace in the house, and I want to know -- I had never really thought about how a furnace works. I'm just trying to learn the parts of it and literally how it functions and what is going wrong. So that when the person tells me that this part is broken or this fan is not working anymore because it's reached a certain age where this type of part fails, then I'm really understanding what they're talking about. And now I can make a choice. Sometimes I've made the choice of, "You know, it turns out that I can find the instructions on YouTube and repair this part myself. I can just order it online." Now this thing that seemed completely inconceivable to me, which I had no idea -- I had never looked on the inside of my furnace before. A week later, I have this part that came off of the internet, and I have a YouTube video that's five minutes long, and I'm doing my own repair in the furnace. Same with, you know, the toilet valve not working. Home ownership challenges you with so many of these things. Most people will do the kind of thing that I'm talking about. Sometimes you're like, "Okay, well, this is a problem that even after looking at the YouTube video or whatever, I'm still not confident in my abilities. I don't want to electrocute myself. I'm gonna rely on someone who's been doing this." **Jackson** [01:52:43] But at least we live in a society you have -- you can rely on it sometimes. **Steph** [01:52:46] At least I know what I'm paying for, as opposed to just, "Here's... maybe it's solved, maybe not." I need to understand what the problem is. Most homeowners go through the same process, but then we don't do it when it comes to education, healthcare, or other things where we're always trusting accountants or whoever it is to be doing the right thing, as opposed to trying to understand how it works. Maybe you can come up with a much cheaper approach, solve the problem a different way, or avoid the problem entirely. Once you're educated about it, you can make those decisions. If you're not educating yourself about it, you're allowing these predatory systems to live on top of you and extract your money, your time, your resources. There are entire industries that are just really good at doing that. Their job is to extract dollars out of people who don't know what they're doing. I faced this problem over and over again in different ways. Now I'm just trying to be more conscientious about when I'm letting go, when I'm doing it. This is a place where I don't know what I don't know, and even after some cursory research, I know that I'm not interested in getting a full education on how to become an electrician. **Jackson** [01:54:31] You're not letting the map become the territory. Patrick Collison talked about how just visiting a city totally changes your relationship to it. **Steph** [01:54:59] Yes. **Jackson** [01:55:00] Another example would be the first time I rode my bike around LA in a meaningful way and covered a lot of ground. It created a connectivity of the city that I hadn't gotten from driving and following turn-by-turn directions. In a broader sense, what you're really describing is the compounding that happens with agency, either gaining agency or losing agency. **Steph** [01:55:11] Yeah. **Jackson** [01:55:11] My friend Jason has this thing: "Confidence is the memory of success." So much of this conversation and how you live, but this example as the kernel of it, your default is, "Hey, I'm capable, I'm smart, I should probably learn how this works at a very basic level." Then I can decide if I want to go deeper, hire somebody, or whatever. The more any of us opt out of that, the more likely we are to opt out of it next time. That's how you gradually gain the parasite. You lose your agency. **Steph** [01:55:46] What's the point of being alive? The world is so complex, and that complexity is so beautiful. The fact that a person is literally just an electrician, and all day, every day, that's their living and breathing, understanding how houses and places are electrified, I just think that's amazing. So I'm curious about it. When I'm dead, I probably won't have time to think about electricians. This is the time to think about electricians. I want to find out what they're all about, what makes them tick, and why they... The world is really rich. There are so many fun things, and you end up learning so much. It might inform another part of your life in a way that is totally unexpected. **Jackson** [01:56:37] Yeah, there's this old quote where it lists all these things that a man should be able to do. **Steph** [01:56:41] Oh, yeah, I love that one. **Jackson** [01:56:42] "Specialization is for insects." **Steph** [01:56:44] Yes, it's a great quote. ## [01:56:46] Investment and "selfishness" in extending your light **Jackson** Another theme about your life that ties into what we were just talking about is a theme of investment. At least it ties in around compounding, I feel. Which is to say, you invest in tools, you invest in style. You obviously talk about this with products and the "buy wisely" stuff. You seem to have almost a non-necessarily purely commercial, but investing-oriented or attuned to what investment means across your life. So I'm curious what you've learned about investing time and money. **Steph** [01:57:15] Most people have a really short time horizon, and I try to have the longest possible time horizon in both directions. We've been talking about it in the scheme of thousands of years, both looking back and forward. How do we -- you know, we're talking about hieroglyphics, and we're talking about needs that people have had for thousands of years in the past, like listening to music and feeding themselves and sitting on a chair. We're talking about what people will remember of what we are doing right now in a thousand years from now. Obviously, your lifespan is short in that, but I think that having a very long-term view of everything -- you know, unless you intentionally are choosing to have a short-term view and say, "I'm choosing to make this decision right now, and I only care about it for the next day." That's fine. But I think there's almost never a case where thinking about the impacts of that decision for the next 10 or 30 years really harms things that much. So I try to do that. I try to think, "How have people been doing this particular thing for a long time, and what is likely to last for a long time?" And then it makes certain kinds of decisions a lot easier. Do I want to spend more time with this person? Do I see myself? Every hour that I spend with you is an hour where, I don't know where our relationship will go ten years from now. I don't know where we will be. But I feel like -- you know, I haven't done any podcasts for a year, and this is the first one that I'm doing because, for whatever reason, I get the feeling that we might -- there's a commonality here. The feeling I have is that it's worth investing my time in. I can't really pinpoint it, but I know that in the past, I've had this feeling before with other people, and I've trusted that, and now I'm trusting it again. I am not a very money-driven person. I guess I'm driven by people having an interest in what I create, that being useful, I suppose, is a motivation for me, more so than money. I'm motivated by having a lot of creative control over the things that I do, more so than the scale of them, if that makes sense. I really learned that the hard way. That's also why the team is small at Obsidian. I care way more about having that fine-grained -- what some would call micromanaging is no longer micromanaging if there's no one to manage, it's just doing the thing. I prefer to do it than micromanage someone who's trying to do it with my breathing down their neck the whole time. So I think that the kinds of things that I like to invest in are having -- I feel so selfish talking about these things. It's so interesting because this conversation has really been about selfishness in a certain way. And I think most people should be more selfish because this is the great thing about emergence. Societies, democracy, things work because people are making -- the reason you can drive down the freeway at 100 miles an hour and not crash into someone is because everyone is being selfish. Nobody wants to crash into each other. And it's marvelous that you are driving so quickly past someone who's equally driving at the same speed in the opposite direction, and the number of car crashes are so few. That's completely driven by self-interest. And so I think that people probably would make better decisions by having a long-term, a more selfish long-term view of what they're going to want 10 or 100 years from now. **Jackson** [02:01:42] But that speaks to selfishness in the stadium of selves sense, because I think people are selfish, but they are selfish in a way that is the **Jackson** of today is the ruler of the arena, and screw everybody else. And then on top of that, the other thing that's interesting to me is it made me think of is people, most people experience the world as sort of like out in. So they are selfish, but it's all about what the world is convincing them of what they should want. I find that actually, people like you, in some ways, we've been speaking like it's originating with you, but actually the world it's in out. The world gets to benefit. **Steph** [02:02:23] That is honestly, I might shed a tear. There was a time 10, 12 years ago where I was really depressed, and I was really struggling with these things. I didn't feel like I had the skills to do what I wanted. I was kind of stuck in a place doing work that I didn't enjoy. And there was a point where I saw this quote by Stanley Kubrick, which I can send to you. I can't explain it or read it, like memorize the whole thing, but the nugget is, however vast the darkness, we must supply our own light. That's the conclusion. He's talking about the universe is uncaring. It's sort of an agnostic view of the universe, which is like space, nature, things are happening whether you like it or not. Cosmically, existentially, we might never understand why we're here, what the meaning of anything is. And that's pretty depressing. It's kind of nihilistic in a way. But if you do what, like exactly what you were saying, and think about taking care of this little flame that's inside of you and focusing on making that radiate out towards the rest of the world, then you can, that's something you can control. You can't control how people are going to feel, whether you're going to have a job tomorrow, how the world is going to change. You don't have much control over those things, but you can control this little light inside of you and try to take care of it and try to figure out what it is, what it's interested in, and let it grow. If you try to learn about that thing inside of you, it will teach you about what you should invest in, because you have interests, you have passions. You can't explain them, but there's things that make you curious. And if you just let that curiosity grow and you go down that weird rabbit hole, maybe it'll lead to nothing, but maybe it will be a milestone that a year from now you'll be like, "Oh, I remember reading that thing about that thing, and now it makes sense to me." **Jackson** [02:04:46] Yeah, an older, wiser you gets it. **Steph** [02:04:48] Yes. Maybe it's the, you know, it's retro causality. It's the future talking to you in the present and pushing you down that path. So I guess what I'm saying about investment is I'm not here to recommend any stocks or something like that. I actually found that I did make some wise stock picking decisions based on the things that I cared about. That had to do with like, "Oh, you know, I've been really curious about this thing, and I think that I'd like to see more of that in the world." And I don't really care whether this makes money really in the long term, but I know that this little candle light inside of me seems really passionate about that idea. And so I'm going to, I see other people who are kindred spirits, and I would like our flames to be in harmony with each other. So let's try to just do that and then you'll see. **Jackson** [02:05:52] Maybe it turns into a bonfire. **Steph** [02:05:53] Yeah. ## [02:05:54] Choosing problems to work on **Jackson** You've written—just to double click on this. You've written about choosing problems. **Steph** [02:05:59] Oh, yeah. **Jackson** [02:06:01] I so agree with everything you just said. But you also care about a lot of things, and you're really capable. **Steph** [02:06:08] I don't care about that many things. **Jackson** [02:06:09] Okay, well, within that, you at least could work on a lot of things in lots of different mediums and disciplines. Maybe since you wrote that piece, I'm curious, are there any revisions on either the advice you gave or just you chose to work on Obsidian with a really meaningful amount of your time? You have this line actually, specifically, I think is, "People work on things that aren't important. The problem you should solve is the biggest problem you are capable of solving." **Steph** [02:06:42] Boy, this is an old essay. I don't even know if I agree with myself. I have to reread that one. I haven't read it in a while. But I think what I was trying to say is that the essay is "Solving Problem Finding" or something like that. Which is, how do we get good at finding good problems to work on? And I think it comes down to the same thing that I've been describing. I started making this little tool to help me learn piano. The reason I did that is because I spent a whole bunch of time playing piano, and it was really frustrating. I think we don't get taught that following those rabbit holes is actually the way that you find interesting problems to solve. **Jackson** [02:07:26] If anything, we get taught implicitly to stop once we have that friction. **Steph** [02:07:30] Yeah. And so I think it's this constant process of finding new rabbit holes that I enjoy. But the things that I care about are not, there's not that many, really. I know, this is one thing that I figured out about myself, that once I kind of started to figure that this was important to me, it helped me have an understanding of what I should do, which is I like making tools. So I figured out that I like making tools at a pretty early stage. And now I'm just living life, sitting on furniture, trying to make music, trying to make food, trying to be a good partner, trying to think about ideas, trying to read books, trying to do the same things humans have been doing for thousands of years. My unique ability in the world is somehow noticing where there's friction and making a tool that reduces that friction. And I'm pretty good at doing that. So now when I go down a rabbit hole, I'm not necessarily thinking, "Wow, this could be a great opportunity to make a tool." Most of the time, I'm just trying to do the thing that I'm trying to do. And then I'm like, "Oh, wait a minute, this could be a tool." But for other people, that's my little flame inside: what tool can I make for myself to help me solve this problem? And maybe other people will find that useful. But for other people, it's something totally different. And I don't know what that is for whoever's listening to this, but that's the thing to nurture. ## [02:09:10] "Nibble and your appetite will grow" **Jackson** You have this little bit, so on the investment theme, you have this essay, "Nibble and Your Appetite Will Grow." **Steph** [02:09:19] Oh, yeah. **Jackson** [02:09:20] Which feels a bit like what you were describing. It's this French phrase that I'm surely going to butcher, but "L'appétit vient en mangeant." **Steph** [02:09:26] "L'appétit vient en mangeant." **Jackson** [02:09:28] Thank you. Appetite comes when you eat. And to me, this feels like maybe the seed, this idea that perhaps the inspiration we need is on the other side of starting or going down that rabbit hole. **Steph** [02:09:42] This is something that I can't wait to learn about when, if, hopefully someday I have kids. A lot of my friends have had kids recently, and I've been hanging out with a lot of babies. It's so fun to see them experience the world for the first time. Everything is new. We get so jaded. Somehow connecting back to that childlike feeling inside of you. That's why I was like, "Electricians? What do I not know about electricians?" Just having that connection to that childlike version of yourself where everything seems new and interesting, potentially. Maybe that's just how I am, but I think that there's value in exercising that muscle of curiosity because the only thing you need is that initial spark of curiosity. What "nibble and your appetite will grow" is talking about is just, if you see something that you're curious about, just go nibble at it and see if it's enjoyable to you. If it is, your appetite will grow. So that could apply to anything. Exercise is a really good one. There's another essay that's related that I wrote about. I forget what the title of it was, but. **Jackson** [02:11:15] It's about showing up in the smallest way possible, right? **Steph** [02:11:19] Lower the bar as much as possible. Just do one pushup, right? **Jackson** [02:11:23] It's amazing how once you're on the ground, prone, assuming you have the ability, it's really hard to only do one pushup. **Steph** [02:11:31] This is classic New Year's resolutions. People are coming up with all these new goals for themselves. "I'm gonna run a marathon. I'm gonna do this or that." The way that you start from having done nothing to running a marathon is somehow you got to run one step. The activation energy, if you can lower that somehow, is the most important thing. If you can just literally do one pushup, one sprint down the driveway, one whatever it is, and you do that every single day, then eventually you'll be like, "I've been doing one pushup." Honestly, no one could do one pushup every day for 30 days. That would be remarkable if someone actually managed to do only one pushup a day. Within three days you're gonna be like, "This is stupid. I can do five pushups." **Jackson** [02:12:29] Also, you tend to feel compounding. ## [02:12:32] Compounding This is the one question I had is like, where have you compounded most? Clearly the curiosity and frankly like the meta nature of this. So yeah, one question I would have would just be, where have you compounded most? **Steph** [02:12:46] Where have you compounded most? I'm actually curious, how would you answer this question? **Jackson** [02:12:56] I'm not sure how deliberate it's been. There's something about people and how I... It's hard for me to discern or separate this question from the "Where do you get your energy?" or "What's your Novak Djokovic tennis ball you like to hit?" I think it's less deliberate, but because it's something that I find so energizing, I have probably compounded something around pushing people and getting deeper into how they work -- the mechanics of how they work. I'm sure there are other things too. I'm pretty attuned to media and products and things that are cool and interesting. I'm pretty attuned to my taste around those things. But again, I don't relate to being someone who is like... Maybe the implicit in my question for you is, "What is a skill that you compounded a lot?" But that wasn't the question, by the way. Compounding can very much be about a disposition. In some sense, it's almost like, where is the strongest link of the stadium of use? **Steph** [02:14:12] One thing that I couldn't have expected to be so powerful, even though it felt so important at the time, was writing the Obsidian manifesto because it actually felt really easy to write. It was just five things. And then what it did in turn is... We only have one or two meetings per year at Obsidian. I have no meetings. My schedule -- if you look at my calendar, there's zero meetings. I have a dentist appointment in a month. I've got our one -- we call them destination meetings -- we have it coming up next week. **Jackson** [02:14:52] Okay. **Steph** [02:14:53] So, we'll spend like five days hanging out. We don't actually really talk that much about work stuff. It's mostly a way to hang out with people because everyone on the Obsidian team lives in a different place. We rarely get a chance to hang out and just kind of get a feel for what people's personalities and everything are like. So there were two aspects to that. One, well, maybe three. One was I feel total confidence that I could disappear for six months and the team would do almost exactly the same thing as if I'm around. **Jackson** [02:15:26] That's a crazy feeling. **Steph** [02:15:29] It's so great because the manifesto and everyone who's working on Obsidian is really passionate about those values. So it's like, hey, we're going to launch this new feature. We launched a feature last year, the Canvas feature. We know that we're focused on open file formats, and there is no such thing as an open file format for Canvas. So it became a no-brainer that we had to create our own format and just open-source it and let other people build on it. I think that there are these decision points that come almost with every project where it's like, should we build it this way or should we build it that way? If there's an option to make the thing malleable and there's an option to make it non-malleable, we're always going to pick the malleable one. So, it's this decision framework that helps everyone on the team just continue rowing in the same direction. I don't have to do anything. Everyone's just working on it together. It has removed a whole bunch of decisions that we didn't have to make because everyone knows what the Obsidian way of doing the thing is. It has completely given me freedom in my time because I don't have any meetings. And it has multiplied my contributions to the world because now lots of people are taking that manifesto and basically running with it. They're like, okay, we want to share that same kind of set of values at our company. We want to do "file over app" with our startup. These are good principles. They're not specific to Obsidian. They're just a way of building that anyone can run with. And so, from a leverage or multiplying, compounding value in the world, that simple act of saying, "This is what our principles are and what we believe in," has had a million X return. **Jackson** [02:17:29] What's interesting is, when I asked the question, I had a thing in my mind, even when I answered it, around effectively, where am I showing up most consistently? Which obviously can lead to compounding, and I've experienced that. I'm sure you have too. But you actually answer in a more important way, which is, to tie it back to finance, it isn't about necessarily investing money every day. It's about putting money in a market so it can compound, so it can multiply. What's cool about the example you gave is actually it was one decision, probably more than a little bit of time, a lot of time thinking about it, but ultimately one decision to write and put something out that you've just gotten to reap the rewards of in some sense for a long time. **Steph** [02:18:13] There are a few things like podcasts, writing software, where you make it once and then it goes out and works. People can read it an infinite amount of times. You don't have to do anything. That is something: the concept of being able to make money while you sleep. If the only way that you make money or get value or somehow earn wealth in the world is by selling your time or some version of that, you will never compound. You cannot compound by selling an hour of your time. I mean, you compound in the sense that maybe along the way you build some abstractions and tools and stuff. But basically, things like writing or sharing these artifacts, whether they be artistic or software, are great examples because you can make it once and then a million people can download it at no extra cost. Those types of things are really powerful. My previous company was completely in the world of bits. It was like, what are the compounding effects we figured out? Factories are compounding machines. They figure out how to make something at scale. And then, yes, of course, they have material costs that we don't have in the software world, but they have a machine that can spit out a million of something. You want to figure out how to build these machines, like a little machine where once you build it once, an infinite number of times that thing can be used. ## [02:19:55] "Caloric energy is precious" **Jackson** On the exact opposite end of the spectrum, meaning the lowest sort of efficiency thing possible, you've written about caloric energy and why it's precious. **Steph** [02:20:06] Oh, yeah. **Jackson** [02:20:07] You say electric energy gives us the freedom to choose how we use caloric energy because caloric energy is precious. This notion that increasingly we're automating everything else. Electric energy for a long time was doing a lot of things that we might need to do physically. And now we're getting to a point where even cognitive things are powered by electric energy. In a world, maybe we're not that close to it, maybe we are, where we actually have most of the quote-unquote work done for us. **Steph** [02:20:37] Yeah. **Jackson** [02:20:38] What types of caloric energy do you find most precious or beautiful? **Steph** [02:20:44] Well, okay, so first of all, that is one of my favorite essays that I ever wrote, and I think it's one of the least popular ones. Nobody cares about that essay. Same with, there's another one called "Earth is Becoming Sentient." **Jackson** [02:20:56] It's on my list. Those two are crazy. **Steph** [02:20:58] Those two essays... Everyone's always like, "All right, file over app guy, give me another banger with whatever software," and I'm like, it's so... you know, my actual... "File Over App" was another essay that I wrote. That was not a draft that had been sitting around in my archives for a long time. One day, some troll account came at me with some dumb thing, and I was like, "You'll see." I wrote that essay... I think I was really mad, and I wrote it up in like an hour and published it. And that's by far the most-read essay that I've written. It's so funny. You can't control anything. But then these other ones that I've been thinking about for decades, that are really at the core of the things that I care about, are not at all resonating for whatever reason. And the weird thing is, last week I was reading Samuel Butler. Do you know this, Erewhon? It's a book from the 1800s about... The Book of the Machines is a chapter within a book he wrote called Erewhon. And it is literally, almost word for word, those two essays. I was reading this, and I was both amazed and sad. It was so weird because I was like, "This person figured out the exact same things that I was writing about, except 180 years ago." You know, the point of "Caloric Energy Is Precious" was just saying how, with the Industrial Revolution, we figured out how to take what muscles can do and turn them into machines. And now we're doing the same with intelligence. We're taking things that are very tedious to do with our mind and allowing a computer to do it, which means a computer doesn't have to eat food. It can just think about stuff using electrical energy. So the calories that we eat can be servicing more interesting needs. And this guy, Samuel Butler, is writing about this almost exactly the same way. He uses the same analogies about horses and oxen. He uses the same analogy about blood from the other one. I don't know how this happened, but it was so cool. I felt so connected to this person as I was reading that part of the book. But he was looking at such primitive examples by comparison. He's like, "When we want to measure something precisely, we rely on rulers." His examples of technology are rulers. Whereas, you know, I'm talking about servers and all these different things. It's so interesting. But anyway, I'm not answering your question. I think the point about that article is that we're constantly allowing ourselves to delegate efforts that previously required our own manual labor. And I still love to... I like to slice vegetables and make my own stew. I'm choosing to use my caloric energy to do that, even though I could buy a ready-made meal. I could hire somebody to fix the stove. I could do everything. I could pay for any part of making a meal, but I probably cook 90% of all my meals, and I love putting in my caloric energy to make my own calories. But I don't think that's necessarily what everyone should do. The point of the article is about the freedom that it provides and to think about what are the things that you actually don't really care about that you could be delegating. And the number of things that you could be delegating are becoming greater. It's kind of like the antithesis of the parasite point. It's sort of saying... I mean, for me right now, I've been learning... I've put out more side projects than ever before, mostly because I don't really care about the quality of the code with that, and I'm just using the new AI stuff so much. And I have a really good sense of what I want out of the tool, like these random little piano things. And I've gotten pretty good at leveraging those tools to write code. It does... like, the output is what I want. And so I can focus on... What I want to do is learn how to play piano and use my caloric energy to move my little fingers around so that I make music. **Jackson** [02:25:34] Right. **Steph** [02:25:35] And-- **Jackson** [02:25:36] If you wanted to share that with others in a way that they could use, you would have also had to previously spend a whole bunch of caloric energy. Now, perhaps the beautiful thing is that you can still do that and spend far less time on the mechanics of it. **Steph** [02:25:50] To do what I did with some of these little tools that I made, I would have had to spend at least a year or two learning how to code a MIDI controller or something like that, so that I can plug in the USB into my computer to my Yamaha keyboard. [00:00:00] Right. [00:00:01] And, but by the way, you would have also had to previously spend a whole bunch of caloric energy if you wanted to share that with others in a way that they could use. [00:00:07] Right. And now perhaps the, the beautiful thing is that you can still do that and spend far less time on, on the mechanics of it. [00:00:15] Yeah, to do what I like this, these some of these little tools that I made, I would have had to spend like probably at least a year or two, like learning how to code MIDI controller or something like that so that I can plug in like the USB into my like computer to my, to my Yamaha keyboard. **Jackson** [02:26:07] That's cool. I read that piece. It's funny you mentioned that it's underrated. I read it a while ago and didn't really think about it, and then it started to find a foothold in my mind. I started to think about it more and more and more. ## [02:26:21] "Earth is becoming sentient" The other piece you mentioned in the theme, perhaps, of where we're going and the way that we are building a new kind of intelligence is you call the sentient Earth, or why Earth is becoming sentient. It's a bit long-winded, but I thought it would be worth reading a few excerpts of this, although I think people should read the whole thing. You say: Earth is not a vehicle but a body, the body of a planet-sized being that is developing senses and intelligence, a will, and even the ability to reproduce. We are cells building this body and maintaining it. The Earth's mind is emerging, mind in quotations, and then invert the theocentric view that artificial intelligence is the coming of a God, a super intelligence inside the machine. Rather, humans are inside the super intelligence. We are inside the Earth-sized machine. This super complex, super intelligent superorganism will not try to destroy us for the same reason that no human wants to destroy their own blood. Then there's one more bit of it in another excerpt from your essay, that really old one on chaos, that I thought were interesting to pair together, especially in this moment where there's lots of question about what it is that we're doing and whether or not we should be building this, and whether it's going to be good for the world or bad for the world, or what it means to be human. I was curious to pair them together. The last paragraph from Earth is becoming sentient, you say: Earth has inherited what all living things share, the élan vital, I'm sure I'm pronouncing it wrong, vital, the will to live, the abhorrence of vacuum. Earth is imbued with the desire to spread, and we are watching it undergo its first mitosis. With rockets, we are giving Earth spores so it may reproduce. And then from the chaos bit: Decision-making becomes relegated to algorithms, but agents of chaos and pioneers are constantly being born. Our free will is relegated not because of an omnipotent power or universal order, but because of a system we ourselves created that reinforces the very course we have set. Our identities are constantly being funneled towards understandability, and yet something in us is unpredictable, not because of entropy or serendipity, but because of a bug, a malfunction, a short circuit that our brain always seems to find, a fuse that gets blown. We challenge the predictions, and that chaotic force unbalances any possible calculation. Even those calculations that attempt to correct for our unpredictability cannot fully understand the rhyme or reason of this odd gene. The fact that it can't seem to be codified is what keeps us from truly falling into the singularity. I don't have a specific question here, but I thought it was really, you wrote the Earth piece obviously recently in light of how much has changed, and you wrote this other piece 13 years ago. Both of those ideas to me paint a not necessarily too prescriptive, but optimistic and, in some sense, like deeply human, maybe human's the wrong word, but deeply inspiring picture of where we might be going. That there's something inside, there's something natural or something innate to how life is shaping the universe for itself. **Steph** [02:29:55] Yeah. **Jackson** [02:29:56] Amidst all this doom and gloom that we're going to get zapped or that we're going to build a God who we're going to, any of these possibilities, there's something in that. Do you, is there a connection there for you? Is there anything hearing that back that comes up? **Steph** [02:30:10] I haven't read that old essay from years ago in a long time. It's interesting because that one was a stream of consciousness. I wrote that essay all in one go, and it wasn't even an essay; it was just a note from my archive somewhere. Whereas the one from recently, I spent a lot of time thinking about. I do think, in a way, it comes back to the point about selfishness that I was making, which is that I'm a big believer in the concept of emergence. Complex systems come from simple things doing simple things within a simple set of rules. Your blood cells are governed by relatively simple rules, and they're just doing a function in your body. I have never met someone who said, "I wish I didn't have blood or blood cells." When I hear people talk about their fears of AI and superintelligence, I'm like, "Why would this thing want to destroy the thing that is taking care of it?" We're literally inside of this thing, maintaining it, taking care of it, connecting the wires together that make it possible for this thing to even have thoughts to begin with. We're inside of this system. We're the blood. We are governed by relatively simple rules, whether we find that dissatisfactory or what. But our rules are not that complex. Human beings have relatively, as we've been saying throughout this conversation, our needs haven't changed that much. We're just trying to live life, eat food, reproduce, maybe find some meaning along the way, build tools, make stuff, and try to continue this process of complexity that nature seems to be pointing towards. And so within a system that is emergent, it relies on all of the individuals within that system to act in a selfish way. The *élan vital* that I keep pronouncing, is the idea of this French philosopher, Bergson. I never actually read his whole deal, but it's just kind of the idea of, "Why do things seem to have this natural impetus of life?" Why do things want to be alive? Why do they move forward? Why does nature seem to, like when you back a dog into a corner, it attacks you. What is the reason that living things have to live? Whereas a machine, you use your computer, you turn it off, the computer doesn't care. It's like, "Been turned off, it's fine." Whereas humans and nature have this striving nature to them. We're imbuing the earth with striving. We're creating this system that is wanting to strive. Weirdly, capitalism is kind of like a kind of equivalent to natural selection in the sense that it is, coming back to that duality of, "Should I have pursued biology or should I have pursued design?" Industrial design is living within, or UI design is living within a capitalistic framework, whereas nature is living within the natural selection framework. Both are governed by a similar thing, which is the weak will die, and only the strong will continue to evolve and spread. The reason we all have iPhones is because evolutionarily, within the capitalist system, they were fit, and they forced themselves to reproduce. **Jackson** [02:34:03] Yes, yes. **Steph** [02:34:05] I'm very optimistic about this because I think that humans are essential in the complexification of nature right now. We're like the blood cells, and I'm okay being a blood cell. I think that's the part that people are not happy about. It's the constant Galileo-type moment where people are always feeling like they're the most important thing in the world, and that computers are these Terminator-type scenarios. I think it's kind of boring. It's just very us being stuck in some kind of way. **Jackson** [02:34:42] We're stuck in our part of the ladder. We're only able to think about the next thing as an adversary on our level or something. **Steph** [02:34:48] And literally at the same scale, like physical scale. We don't care about blood cells or ants or anything that's small because they're small. But if the thing that we're that is coming about is the size of a planet and it's interacting with other planet-sized things, it is existing at a scale that we don't really understand and we don't relate to. **Jackson** [02:35:12] But it doesn't mean we're insignificant. **Steph** [02:35:14] No, do you think blood cells are insignificant? Or mitochondria? The mitochondria is one of the most successful things that's ever been invented. It's amazing. Nobody on Earth wants to not have mitochondria. So I think it's very optimistic for humans because we're essential to this complexification of nature, and we will probably keep going. I don't have too many fears about our self-destruction. **Jackson** [02:35:46] Have you read *The Beginning of Infinity* by David Deutsch? **Steph** [02:35:50] No, but I have listened to quite a few of his podcasts. I think he's fascinating. **Jackson** [02:35:54] I haven't read the whole book, but in one of the first chapters, he has this section that is just so on point with everything you're saying. He talks about these two core ideas that have defined the Enlightenment or this post-scientific revolution. One, that man is insignificant. It's a **Steph**en Hawking idea that we're trivial beings on a trivial rock in a vast universe. **Steph** [02:36:14] Right. **Jackson** [02:36:15] And the other is the spaceship Earth idea, that we so fortuitously happen to be on this planet that, in a vacuum, happened to be hospitable to us in a cold, dark, inhospitable universe. And Deutsch's point is actually you would be better off believing the exact opposite of those two ideas. **Steph** [02:36:31] Hmm. **Jackson** [02:36:32] In fact, we are significant. We have explanations that are able to describe what is happening on galaxies so far away from us. And two, and more importantly, the Earth has been shaped by life and by us to be our home. He's like, "I'm writing this from Oxford, England. If it weren't for technology, I would die in eight hours from frostbite." There are very few fossils of old people. 99% of species are gone. The replacement rate on species going extinct is barely over zero. **Steph** [02:37:02] Right. **Jackson** [02:37:03] And yet, actually we are a critical part. We shouldn't just be grateful to go back to nature the way it was. We are a critical part of shaping this habitat we have. It feels like a really cool parallel and matching shape to your idea. **Steph** [02:37:17] Definitely. I really like his definition of explanations. I think that is something that I really retained, and I think it was influential for my essay about being concise. It's back to that idea of memifying your ideas even within your own mind. The "spaceship Earth" idea, that's from Buckminster Fuller. He was very influential to me when I was first studying design. When I heard that, it was a mind worm. I could never unhear the phrase "spaceship Earth." But the more I thought about it, that's why I came up with the word "thinking Earth." It's like "spaceship" implies that it's a vehicle. **Jackson** [02:38:04] A vessel that's empty, that's mindless. **Steph** [02:38:06] Well, I'm open to different interpretations of the word "vehicle," but "spaceship" is like you're either on the spaceship or in the spaceship. We're traveling with the spaceship. How did the spaceship come about? I think what you're saying that resonates with "thinking Earth" is more like, yeah, it's not a vehicle, but a body. It is like we are growing on top of it, like a moss or something like that. We are shaping it. We're digging holes into it. We're starting to put out spores around it. This thing that was just barren rock is like a moldy piece of cheese in your fridge. You find this thing and you're like, "Oh, God, this thing is alive now." You zoom out, and it looks like a petri dish that is starting to grow with stuff on it. And it will spread because that's the "nature abhors a vacuum" kind of idea. It wants to spread, and we are literally building the spores to spread it everywhere. I think that's great. I think that there should be trillions of humans in the universe. Yes, there will be more suffering, but there will also be so much more joy in the universe if there are more people. And I mean humans or living things in general. I think there should be more living things out there. ## [02:39:32] Busy being born and sharing along the way **Jackson** We're about to wrap up. One of my final questions: you have this really old essay where you have a professor who quoted Bob Dylan, "He not busy being born is busy dying." It reminded me, there's this book called *Tomorrow and Tomorrow and Tomorrow*, this novel I really enjoyed. And in that, there's a line that somebody says, "It isn't a sadness, but a joy that we don't do the same thing for the length of our lives." We've talked about this. In some ways, this might be a reiteration of a question that I've already asked, but you've done so many different things, and you continue to be prolific. There's one other line in there. You say you should be continuously running from the pack of ravenous dogs while dropping a trail of fresh meat behind you. You're connoting this idea of just continuing to reach out into the unknown. You're teaching along the way. You're talking to those past selves. The question that came to me in thinking about this was, what is most important to hold on to? **Steph** [02:40:36] I think I wrote that essay pretty long ago. I was working on this physical product at the time, and we were so ruthlessly copied. A company completely ripped us off, including everything that I had been working on for years. I felt so frustrated. And then I really changed my outlook on it. I just went through that pain as information process. The stuff that I've done over the years has been copied so many more times since then. It's a nice reminder of just not feeling bad about that at all, like I did back then. In fact, I try to make things easy for people to copy. I've open-sourced a lot more of my stuff over the years. Even old stuff that wasn't started open source, I ended up sharing completely. It's like that idea of dropping meat behind you. It is a compelling force to basically push you forward. Just keeping giving everything away is a mechanism to force my own curiosity. I don't want to rest on my laurels. I don't want to stay stuck in my old place. So if I just keep feeding these ravenous dogs behind me, then that's going to force me to keep running. If I stop doing that, then maybe I won't have enough will to keep running. **Jackson** [02:42:09] Maybe that's the constant. ## [02:42:11] Love and freedom Okay, my last question for you is that you just got engaged pretty recently. Congratulations. **Steph** [02:42:17] Thanks. **Jackson** [02:42:17] What have you learned about love and yourself from your partner? **Steph** [02:42:20] God, I wrote an essay about love like a year ago, and now I've learned so much more about love recently. I'm like, I gotta edit that. It's interesting. We have, I think, a mutual friend, Nadia Egba, and her partner, Delian Asparova. They got married and they have an interesting podcast. I've been meaning to listen to it. The only thing I remember is this quote, because I haven't listened to the podcast yet. **Jackson** [02:42:51] It's just like being in jail. **Steph** [02:42:52] Yeah, and I heard that she was like, "Marriage is like being in a jail that you chose," or something like that. That's the only thing that I heard, and I was like, wow, I'm about to get married. It doesn't really match my experience of a relationship where I... And so I haven't listened to the conversation, and maybe she meant something, like maybe they just clipped that bit out. **Steph** [02:43:20] Can't trust them as a teaser. But I kind of feel like, to me, love and finding someone in your life is something that is one of the most freeing feelings I've ever had in my life, where I could see how the kind of commitment to someone could feel like it's closing other avenues, other people that you might spend time with. To me, it's been incredibly freeing in the sense that, in one essay I wrote about love, I was describing it as having a safety net that allows you to do something that is more scary than you could have otherwise done. If you have someone in your life, and I mean, love can be expressed in many ways. Maybe that person is someone in your family. I think someone who is a romantic partner has a view, a more full picture of you than probably anyone else in your life. If you find someone who's really great for you, they give you this feeling of always having a safe space that you can come back to, even if you make mistakes, even if you are going through pain. They're a person who can challenge you to go and find those edges and trust that they'll catch you. That is a really, really beautiful feeling that I had never experienced until I met my partner. So that really changed my life. And I have no advice on how to find or how to do that. People would always ask me about this when it came to like, "How did you find your co-founder?" when I was working on Lumi back in the day, and even now Obsidian. I don't have it. I don't know how. I think it's just luck. I have no idea how to. **Jackson** [02:45:18] You know it when you find it. **Steph** [02:45:20] Yeah. I guess the only advice is just to have high standards and to keep yourself to that standard, and to not settle, I suppose. **Jackson** [02:45:30] You care a lot, and you show up in the world in very specific ways, which I think helps. **Steph** [02:45:35] Yeah, but maybe that's not how we found each other. But it could be. I think that definitely helps to increase your surface area as a human being that people can find out about you in some way. It is very powerful because it's created a lot of new relationships, non-romantic ones, for me. I could see how, for some people, it would create a new romantic relationship if people have access to you and can find out about you from the outside. Yeah, I wish I had better advice on that. **Jackson** [02:46:10] I didn't ask for advice on that. **Steph** [02:46:11] No, no, I know. It's an interesting thing because it's come up a lot recently. **Jackson** [02:46:15] I mean, I'll take advice, but I don't know. **Steph** [02:46:17] Yeah, it's come up a lot because I think it's so. We're in such a weird time when it comes to love and all of those things, the kind of dating apps and like, how do people meet each other? Touching grass, all these types of things. We're trying, we're like child-rearing. There are all these weird subjects that are kind of, I think we're in a malaise, societally, in terms of how we find each other and connect on these things that are really deeply animal. The more we transcend ourselves as beings, the harder it is to be connected to what makes us human, which is we're animals. **Jackson** [02:47:02] Yeah, but maybe more than any of that, the first thing you said, what can you want in a partner? You want someone who sort of gives you the freedom to shine, right? Who can protect that flame? **Steph** [02:47:15] Yeah. **Jackson** [02:47:16] And that's the most beautiful part of love, I think. **Steph** [02:47:20] Yeah, that is the kind of thing that you know it when you feel it. I guess I did have that essay, "Product Market Fit." I don't know if you know that one. It's something like, if you don't know whether you have product market fit, then you probably don't yet. Love is a little bit like product market fit. You know it when you have it. **Jackson** [02:47:43] There's our sound bite. **Steph** [02:47:44] Uh huh. **Jackson** [02:47:45] This was really, really fun. We went way over. Thank you for being so generous with your time and your wisdom. I expect this will be quite energizing for many people, so thank you. **Steph** [02:47:55] Thank you. Thank you for having me.