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On notetaking and open-ended conversations
Cosmic cities, Arthur Wesley Dow, 1913
Conversations are streams: they pass by without leaving much behind. But if you add a notebook—if you write down short summaries of what you talk about so you can return to it in later conversations and expand—then you have a landscape for the conversation to flow through, and this changes it in interesting ways.
When I started writing summaries, I thought it would be a small change. I already kept a detailed journal—I could just as well keep one for conversations, too. I could jot down a few notes about the key ideas, turning a two-hour conversation into 400 words or so. After a few months, however, it became clear that these notes were in fact not a small change. The notebook had entirely altered the shape of my conversations.
Because I had the notes, I would review them if I was to speak with the same person again, adding comments about thoughts I’d had in the interim, rank ordering which topics I wanted to revisit, and so on. This way good ideas and topics would not be dropped but revisited and expanded. They would be connected to new insights, merged, and refined. Through this, the conversations became richer. They became more useful and interesting.
The conversational stream was flowing through a landscape. On its banks ideas would wash up. Gradually, the banks would move, too—the landscape is shaped by the flow of words into a canyon. A canyon that shapes the stream of words in turn.
I don’t write down the conversations I have with most people. But there are a few who I keep coming back to—friends with minds that are forever churning, minds like mysterious machines I can never fully grasp but am continually delighted by. When we talk they all take me to different places; when I add a notebook they all go deep.
The first conversation I wrote down was with Torbjörn, a software engineer who has an uncanny ability to guess my thoughts. When he gets excited he SPEAKS IN ALL CAPS, and he gets excited about everything.
At the time, we talked on the phone once a week for about two hours. I would set off from my house toward the ocean and cross into the nature reserve. Walking along the ravine and the cliffs for a few hours, I would talk to Torbjörn about open research questions and software projects we were involved with. He would ask me for strategic advice about his consultancy. We also talked about our relationships, aliens, the ravings of the world around us, mopeds.
While talking, we would take turns jotting down keywords to aid our memory, and then, when I got home, I would add what we had said to my note-taking system. I revised old notes in light of how our thinking had evolved, adding new links between different ideas, and so on. (For this particular conversation, I used Obsidian. But the tools are not important. And I roughly follow the note-taking strategy that Andy Matuschak outlines here. But that is not important either.) If Torbjörn wanted some of the notes, I would email edited excerpts to him, so I didn’t have to format my notebook in a way that makes sense for him to read.
First, I mixed the conversational notes in with my other thoughts. But I’ve since found that keeping the conversational notes separate from other notes is better—it creates a stronger sense of place. Now, I enter the Torbjörn notes, and all past conversations flow up. Mixed in with the other notes, they were diluted. (I do interlink it heavily with other notes, though.)
During the week or so until we talked again, I would occasionally revisit the notes and add a thought or two. It kept the conversation alive in my mind. I’d update a list of topics I wanted to cover next time, shuffling their relative importance.
This priority list, which was added to deal with the mess the notes became after a few weeks, turned out to be important. It was a ratchet—whenever we happened on a good train of thought, the priority list ensured that we would not drift back down to a lower-quality conversation path.
Good ideas would bubble up and push others down until they eventually fell off the list. We never again had to speak about Trump. We spent more time on the best ideas than we would have unaided by notes, but without limiting open-endedness. It also meant the best ideas were improved through competition.
Torbjörn and I are both highly divergent minds, so we still went off on tangents all the time. But since I had the priority list written on my hand, I could compare the tangents to the most interesting paths we had already gathered.
Sometimes I would cut us off almost immediately, sometimes I would let us go for twenty minutes as I paced the pier watching the mercury-colored winter waves wash in as snow broke on the surface. By adjusting how long I allowed the conversation to drift, I could tune the amount of randomness in our search algorithm, so to speak. Do we want to narrow it down today and focus only on the most important topics? Or are we stuck climbing a low hill and so want to roam widely? What is the optimal amount of randomness?
The notebook made these meta-reflections on the conversation salient. I wasn’t just reacting to the last thing to jump out of Torbjörn’s mouth (”WOULDN’T IT BE COOL TO MAP WHAT THE STRUCTURE OF BAYAKI SINGING WOULD BE IF IT WAS TURNED INTO A POLITICAL SYSTEM?”), I was also modeling the overall flow of the conversation. (Is polyphonic singing and politics the best thing we can think to talk about? Are we really on the main branch here? And all of these things that Torbjörn is screaming—are they more or less generative than usual? If less, in what way can I change the way I probe the conversation to make us more generative?)
With my wife, I do it a little differently. Once a week or so, when the kids have fallen asleep, we’ll lie in separate beds—Johanna next to the baby, and me next to the 5-year-old. We’ll both be staring at our screens. Unlike the notes I keep with Torbjörn, these notes are shared. They are a bunch of Google docs.
As we talk, we’ll move between the documents, as if moving around a house.
“Where are you?”
“I’m in the priority list.”
Standing in the priority list, we talk about what we needed to focus on. There are many interlinked rooms leading out from the priority list: one is for our children’s education; another one is the portal where we enter our psyches, to talk with our suppressed parts; a third room is a massive document where we are extracting notes from old church protocols, trying to wrap our heads around the history of forcing the indigenous Sami population into schools in the 1700s. There is also, of course, a dreadful room filled with chores.
Walking these rooms, we’ll gesture at things with our cursors as we talk aloud. We’re not really writing—though, over time these rooms contain many words. Small notes made to clarify a point or to aid our memory. Over time, they have been expanded and organized: it is the scaffolding of our conversation, left behind as a structure to think in.
By having the conversations inside the notes, they become more focused and detail-oriented than the conversations I have with Torbjörn. I guess this comes down to the fact that our priorities and past thoughts are more salient when we are hanging out inside them. It constrains our associations more. With Torbjörn, the structure is soft and largely invisible. I rarely mention the topics I have decided on—so he’s in the dark, which adds a lot of randomness to his rants, and I often forget what I meant to say too, if I get excited by a tangent. With Johanna, strolling about talking in our rooms of words, we get fewer surprises and more things done.
(This could also be a reflection of the fact that Johanna, unlike me and Torbjörn, is a disciplined and systematic thinker. She will not let an idea into her mental representation of the world until she has submitted it to rigorous tests; I convince myself of a hundred new ideas every day and discard 99 once I’ve experienced how stupid it is to believe in them.)
My impression is that talking inside the notes allows me to more deeply internalize ideas compared to keeping a private notebook. Johanna and I have to struggle hard to reach a shared understanding detailed enough for both to feel that the document represents our thought. It scrubs the ideas in. The more soft back and forth I have with Torbjörn does not require an exact shared understanding, as long as our conversation is generative on both ends.
But keeping a notebook with someone else is hard. The few times I’ve tried with people not married to me, the notebooks have degenerated into slums. People will usually build their own corners, afraid to mess with the words others have put in. And so the thoughts are not properly integrated, they just sprawl, and are not tended to with love. And if someone does try to integrate the collective thoughts, if someone edits other people’s notes when they are away—well, there are few things as frustrating as having someone mess up your structure of thought so it becomes less useful to you.
You should be careful whom you do this with. So having a spectrum of conversational canyons is useful. Some conversations you wish nothing else than to have them flow away into oblivion. Others, you want to constrain and direct their force without limiting their flow. You want to carve a conversational canyon.
And sometimes you want to live in it too.
If you’ve made it all the way down here and don’t feel that you’ve just wasted ten minutes, consider giving the essay a like. It helps others find it. And it makes me happy.
Appendix: Some thoughts on software designs that enable this conversation pattern
Gwern’s suggestion for how to design internet communities to allow for conversation on different time scales:
One could imagine a Reddit which integrated chat, links, & wiki pages to create a smoother transition between nodes and directly support promotion:
a subreddit has a chat channel which defaults to anonymous and is not logged or archived, with the minimum possible moderation;
blocks of fast-time chat (seconds to minutes), however, can be highlighted and right-clicked to automatically turn into a comment on a link or their own text post, ‘promoting’ them up one level to slower-time, where they can be discussed over hours to days;
such comments, perhaps on some topic of sudden new interest, may be further selected, and transcluded into a new wiki page devoted to that topic (crude, but a starting point as a comment index), which can then be hand-edited later to add in additional commentary, links, citations, etc;
these pages become a long-term resource for that subreddit, and perhaps turn out to be of broader interest, being crossposted to other, bigger, subreddits,
and, amazingly enough, eventually reach /r/all where it is pushed to all users as part of their default feed—adding a new thing to the global ‘common knowledge’, which (return to #1) some other subreddit chat might idly discuss for a while and then make an unexpected breakthrough, kicking off a new cycle.
Another thing I have considered is doing transcriptions of my conversations. I could record the conversations and upload them to a transcription service - and all of a sudden the entirety of the conversation is searchable. That is pretty neat.
If you have the conversations transcribed, you can also build an AI bot that you can ask questions to and have it search through your past conversations and generate answers based on what you have said in the past. Maybe using the method I demonstrated here.
You can ask the AI:
“When we talked about graph-based operative systems, what did we say about how that could interact with spaced repetition?” Or: “When did we talk about trust graphs?” And so on.
You can also make the bot provide links to the parts of the conversation that it is synthesizing in its answers.
Once these types of AI enhancement get cheap and accurate enough, one could have them run in real-time. It would be a third party to the conversation, who remembers everything that has been said. It could prompt you to go deeper on promising ideas. It could find analogies between concepts you’ve discussed months apart. It could automate the self-moderation needed to have deep, generative conversations.