Getting compound interest on your thoughts with Conor White-Sullivan

Welcome to the third instalment of Mindful Makers, where we interview highly creative people and ask them what they think about creativity, productivity, and building products that matter in today’s connected world. In the previous editions, we chatted with Buster Benson and Khe Hy. Today, we are pleased to take a deep dive into the thoughts of Conor White-Sullivan, founder of Roam Research.

Conor has lived many lives already, lives that involved connecting the dots and approaching challenges in novel ways, which may explain his obsession with finding interesting intersections within a knowledge graph. He studied anthropology at the University of Massachusetts, taught classes on stoicism and practical philosophy, created an online town common which was acquired by AOL, and worked on special projects at the Huffington Post, reporting directly to Arianna Huffington. He is now fully focused on Roam, a note-taking tool for networked thought—and, in my humble opinion, the best metacognition tool out there.

Conor White-Sullivan and Anne-Laure Le Cunff interview for Ness Labs

You’ve been working on Roam, or at least the concept of Roam, for quite a long time now. What inspired you to start building this tool in the first place?

I was originally interested in figuring out how you could figure out what’s actually true online. Wikipedia is still bottoms up with institutional news. Their trust still comes from legacy. A thing that gets vetted on Wikipedia has to have first been published in the New York Times or some other third party. And I didn’t think that that was going to work going into the future. So, the first problem that I worked on was trying to do this for hyper-local politics.

The idea was that you had the people who actually lived in a town able to crowdsource the pros and cons of any policy change that was going to happen in that town. You could bubble up the best ideas for an idea, or the best ideas against an idea, or for a local candidate or against a local candidate, etc.

But the more we did it, the more I saw that storing ideas as just strings of text doesn’t actually allow you to do any of the more challenging work. Especially if you have a large group of people and no one person’s going to be able to read everything that every single person says, you need a better way to actually see the structure of arguments, or the structure of trade-offs in a decision, or all the competing factors in the decision.

I eventually figured out that a simpler problem to solve was: how does one person take 20 different people they’re reading and start to create some sort of synthesis or math-like map of the idea space, across a bunch of different books that they’re reading, or a bunch of different observations or conversations that they’re having, and gradually be able to index into the individual things? So somebody else who is reading their synthesis can check and say, “Is this summary actually reflective of the underlying idea?” Or, “Does point A actually imply point B?”

The specific thing I found really helpful was Mortimer Adler’s “How to Read a Book”, where he talks about this idea of syntopical reading. There was a project in the 50’s. It was called the Great Books Series, where this guy, Mortimer Adler, and I think it was Encyclopedia Britannica, they got all the books of western canon and they indexed all the places in Hegel and Kant and John Locke and all of those classic books of western thought, and they indexed all of the different ideas that were being brought up in there.

And they summarised the core ideas and the core differences of opinion across all these different people and then indexed back to where in each of these books it’s said. I thought that that was a really cool project that would be a lot better if it was digital. And it would be a lot better if it wasn’t just these 50 books based on this editorial decision made that those were the 50 books that really mattered. I was like, “I want the syntopicon or synopticon for physics and for ontology and for the Vedas and Upanishads and things that aren’t just in the western canon.”

Those were where some of the original ideas came from. We’ve always wanted to build a layer on top of the web where every person can have their mental model of how the whole world works, and they can start to share ideas across everything.

You’re mentioning two different planes almost. You first mentioned speed of thinking, but taking notes and creating an archive of your thoughts—that encourages depth of thinking. How do you see Roam helping with connecting the two, thinking fast and thinking better?

I think that you need to be able to get compound interest on your thoughts. Good ideas come from when ideas have sex: the intersection of different things that you’ve been reading or different things you’ve been seeing. So you can have better ideas faster if you are actually reviewing the old things and you are building up. You’re not throwing away work.

A lot of times people forget everything they read in books and they’re not often able to think, “Oh yes, this thing that I just read reminds me of this book that I read six months ago, or two years ago, or five years ago.”

I think solid foundations do make you faster in the long run. That’s the core idea in the Zettelkasten. You move a little bit slower as you go through a book. But you get some nuggets of thought articulated that then end up allowing you to produce, and when it comes time for you to write something, it’s much faster because you have already done a lot of the work ahead of time. And so you’re not duplicating it over and over again.

That makes sense. Talking about building a foundation… I read a tweet from Tiago Forte recently where he was saying that after a while, when you’ve been taking notes for a long time, the extra benefits of new notes start to wane. You don’t need to take as many notes anymore because you keep on reusing what you’ve written about before and just connecting the dots instead of taking more notes. Do you think that’s the case?

I don’t actually buy that thesis. I guess it depends on how far into new territory you’re trying to push yourself. If you learn the pentatonic scale and you learn how to play blues guitar, you can just be like, “Ah well, now I know those fundamentals and so I’m just gonna play blues all the time. And I don’t need to learn new stuff because I’ve got a steady repertoire and I can bang out great blues riffs really easily.”

But you can also keep doing the same deliberate practice and keep the same level of intensity if you’re pushing out into new territory and then you’re incorporating those new notes. I would actually say, as you get a more developed Zettelkasten, you get more evergreen notes.

Then one new thought can generate seventy new thoughts, because there’s more stuff to connect it to inside. So I think the connections can increase. You might take longer when you have a new idea to connect it up to all the old things you’re thinking about, but it can generate more new insight. I read one new observation, and then I can generate more new insight because I’ve got a larger set of things to compare it against.

That makes sense for finding links and connections inside of your own notes. But Roam also allows you to also collaborate with other people and connect the dots across a team. So how does that work? 

Right now, Roam offers real-time collaboration, so you can have multiple people in a single workspace. I think the real opportunity for us is when you can share notes across databases and across workspaces.

If we project ourselves in a year, or two years or whatever, and technology is not an issue, how do you imagine this working in the future? If we’re taking the grandfather of Roam—Wikipedia— with lots of people collaborating on content and connecting the dots. They have a slow moderation system, and there are politics involved because you need to decide what edit is going to be more relevant than another. How in the future do you see all of this work with Roam? 

I see a pretty strong difference from Wikipedia. Wikipedia has this idea that it is possible to get to a single source of truth. Through that slow deliberation, moderation process, there’s a neutral point of view and there’s one thing which just reflects reality, and I think that’s completely bullshit. Roam’s a bit more post-modern in its perspective on how truth works.

It’s more similar to a federated Wiki. Ward Cunningham, who invented Wiki, realized that Wikis don’t allow you to deal with original research. So, what we’re more interested in is, if I like some of your thoughts on meta thinking, if I like some of your thoughts how to use Roam efficiently, and you’ve made those thoughts public and you’ve made this reusable, I can just grab them and put them into my workspace. And if somebody trusts me, they can be listening to my workspace, and they can then grab your notes from me.

And you don’t need to worry about some slow, deliberate, moderation process. If somebody trusts me, it’s much more like Twitter. When I think about the future of collaborative thinking, I think more about how Visakanv uses Twitter of just threads on threads on threads. When he’s making threads, he’s re-tweeting himself, he’s re-tweeting other people, he’s searching through Twitter to find the appropriate tweet for each thread. That’s more what I think about rather than a slow, deliberate system.

What I like about this approach is that I don’t need to trust you because I can go back and click and click and just go back to the source and decide if I feel like that’s a good source or not.

You might need to trust me if I’m the source. If I’m making an original observation, then you need to decide, “Okay, do I want to listen to what Conor is saying about… “

But I get that choice because if everything is linked together I will eventually get back to the original source, so I can decide if I trust you because I will find you, which currently is very hard on the Internet, right? To find out who was the original person who had that thought.

Yup. And you can see if somebody has a critique. There’s a lot of complicated design problems for us to solve when you’re thinking about the multiplayer version of it. But they are still very related to the problems that we have to solve right now. I’ve got a collection of a hundred backlinks that relate to knowledge management, and I’m deciding which of those backlinks I’m pulling up into the body of the page itself. And so taking this big noisy buffer of potentially useful thoughts and then figuring out how I want to structure it and figuring out which one of those basically should be elevated to the body of the article.

Yes, I’m often faced with the same dilemma. Let’s talk about fun use cases. Either as a team working together or an individual, what are some of the most creative use cases that you’ve seen so far using Roam? 

One of the things that pops to mind is somebody who created a Roam page for every ingredient in their house and then they had another page where each of those ingredients had a check box next to them. They would reference the ingredients in the individual recipes they were using. They were able to see just by opening up their recipe page what they already had all the ingredients for. That was a pretty creative use case that sort of was practical.

When I think about creative use cases, the people who are using it for space repetition is pretty interesting, where they’re taking advantage of the fact that you can expand and clap bullets and set a date for something so that it appears in the back lines of a future day. This way they are able to set up basically flash card systems so that they can get information from their second brain into their first brain. That’s been another pretty creative use case that I have gotten a big kick out of.

That sounds amazing. What about discoverability? When I re-read old notes, it’s either because I’m clicking on a link, either one I proactively created or a bi-directional one that was automatically created, or because I know exactly what I’m looking for. But once we think about the multi-player paradigm, how do you think about discovering stuff that other people created? 

Right now we’re focusing on just helping you re-discover old notes that are relevant. There’s a lot of workflows around that, around how do you take raw temporary notes. We encourage people to use the daily notes and to brainstorm and brain dump, and just write all the things they’re thinking.

I think that the first thing that we’re interested in is, how do you build systems so that it’s easy for you to take those and gradually refine them? There’s a combination of the tool, and there’s the habits people have around the tool. So people are using it for actual knowledge gardening. 

You need to have a habit of tagging something as a to-do to synthesize the idea further, and then periodically go back and review those and write them in a more crisp language, or build up your evergreen notes so that you have this library of thoughts that you are able to get that compound interest on.

There are a bunch of design challenges we’re working on. And there are a lot of things that are going to make it easier. You can do crazy linear algebra stuff over text to find related notes, even if they don’t use any of the same words. So I think there’s definitely a lot of opportunity there for suggesting possibly related notes, but the act of a person seeing the connection themselves as opposed to some algorithm seeing the two words are connected, I think is pretty important, because that’s where you get more insight. The process of drawing the connections is pretty important. So you can’t really automate these things away. The act of drawing the connection yourself is a valuable thing that we don’t wanna take away from people.

I agree. This is why it’s a proper second brain and not just a separate storage place. I want to finish with a topical question. What are some ways you think people can use Roam right now to address some aspects of the pandemic?

There are a bunch of scientists using the tool right now. We actually initially bootstrapped the company by working with a bunch of people in the field of AI research, particularly AI safety. So folks who were at the Center for Existential Risk, and Machine Intelligence Research Institute, and Center for Effective Altruism were some of the earliest people that we were building the tool for. So I talked a lot when we were doing research studies with folks who are modeling pandemics. Hopefully they’re still using Roam and they’re still using it for mapping out their thoughts and figuring these things out.

But I think for most people, if you’re not an epidemiologist and you’ve never done anything in biology, supply chains, or manufacturing, now probably isn’t the time to just start trying to teach yourself everything, to jump into the fray.

Instead, I think it’s a crazy opportunity for people to do deep work, because a lot of the other normal distractions of daily life have been removed. Isaac Newton basically invented calculus when he was in quarantine, Shakespeare wrote King Lear. There are lots of good precedents of people being able to do wild work because they had the time alone with their thoughts. So I don’t think right now is a time for people to just suddenly be like, “I’m going to address this plague.” But I do think it’s a time where people can think about what comes after this. The world is going to look really different.

I mostly think of it as a sort of a window of opportunity for a lot of people to get to spend some time on deep work or just play-work. A lot of times it’s like everything has to be some side project, or some side hustle or some business to get into, but this is a good time for you to think about religion, or mythology, or reading the books that have been on your shelf for forever that you actually want to dive into, and get into some philosophy. I also think it’s a great opportunity to learn a skill that you’ve wanted to learn for a long time.

Thanks so much, Conor! If you want to learn more, here are the other articles in the Roam Research series:

And I highly recommend following Conor on Twitter.

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