In reply to Stop and think by Paolo Valdemarin

This made me stop and think. My company contains a well above average number of actual philosophers, 50% of our team. Some with PhDs. Usually combined with practical technical knowledge. Not sure if it gives us a better handle at the future though. Yet, ‘holding questions’ is something I have returned to a lot in the past months. One of my recent little LLM experiments focuses on it (it’s called WittgenstAIn III), and it routes a question through several philosophical schools of thought as lenses, to hold a question not just longer but also differently.

I started asking myself: how good of a philosopher is this guy? If I were shut in a room thinking about the future, is he somebody I want with me? That’s the test now. Anyone can execute. Fewer people can sit with a hard question long enough to find a better one.

Paolo Valdemarin

In the past week I’ve started three personal experiments that use AI (in this case Claude Code). For each, the experiment lies in automating steps in my cognitive work that are useful or necessary but not the actual cognitive work itself. They’re helper activities, supporting the main task. For two of the three that is the clear focus, the third is slightly different.

The three experiments are:

  • Filtering on interests in my feed reader, let’s call it ‘Weak-tAIs’.
  • ‘Slopsidian’, lifting concepts and argumentation from papers into Obsidian notes, and linking them iteratively.
  • Explore questions with pre-existing ‘recipes’ that take a specific philosophical perspective. Perhaps I should dub this type of language game ‘WittgenstAIn III’.

It started from an automation task, which I mentioned here: manipulating non-fiction e-books. I have a script that I can point to an e-book in my Calibre collection, and then will populate a note with elements from the book: foreword, index and literature list, content overview, all if present, and for each chapter of the book the first and last few paragraphs. This is what I look at and skim whenever I want to gain a first impression and understanding what a book is about, and what questions it addresses or what it proposes. All very Mortimer Adler. From it I can then decide which parts of a book to read more closely, which parts likely contain things I am already familiar with or fall outside my current interest in the book. From those skims I jot down things in my note for the book. This quickly turned out to be useful to me, because it removed the wall between the e-book and my notes by bringing parts of the e-book into my notes temporarily where I could more quickly go through them in preparation for ‘proper’ reading (although in fact it is part of reading).

It got me thinking what other helper activities in reading and filtering I could identify.
Helper activities are tasks that support a main task by making it easier or providing guard rails. Checklists are an example, they ensure that you don’t skip important steps. In most cases nothing will immediately go wrong if you don’t do the helper activity but if you do them the main task gets a little easier to do well. A lot of helper tasks can be regularly automated, like the e-book excerpt script above. Others less so because they contain elements of processing actual texts, like the three experiments I describe here. There perhaps using a model like Claude Code can be of value (and hopefully soon, through local model deployment).

A brief description of the three experiments:

Weak tAIs
I order my RSS feeds by social distance for reading. Part of the reasoning is that I want to be well informed about what close ties write, but I am aware that interesting information likely comes from a wider social distance. This practice has been in place for some two decades and enormously valuable all that time. The most interesting stuff usually comes from the third layer, a folder named ‘c150’, in my feedreader: close enough to know who the author is, and engage in interaction if I want, disconnected enough for them to encounter things I am less likely to have already seen myself. That is the The Strength of Weak Ties (1973) as Granovetter called it.

I also keep a list of current interests, a bit like Feynman’s dozen or so currently favourite problems. For each interest I have formulated a few aspects:

  • what is conceptually interesting to me in a topic (e.g. my interest in EU digital and data policy conceptually is that it forms a geopolitical proposition externally, while being a quality improvement instrument internally that takes rights and societal values as yardstick),
  • am I theoretically interested or more practically,
  • do I have a knowledge fundament for the topic or am I a newbie,
  • is there a link with any long term goals,
  • can it be put into a specific context or tied to a specific issue/question,
  • can I shape or create an enduring practice around it,
  • can I build a bridge to outputs, like blogposts, presentations, or client proposals

My feedreader tracks just under five hundred people writing on the open web. That can easily amount to two thousand postings in a week. I can have several intentions to start reading, one of them is to find and read material relevant to my list of current interests. A reading intention does not do away with items, it’s not a filter to remove material. It’s essentially just a view on the entire set of incoming items in the feed reader that I usually construct in my mind. What if I can construct those views on my screen too?
The ‘c150’ social layer, the weak ties, what do they write about that connects to the fields of interest from my list? Such filtering does not lend itself to text based search based on fixed terms. I usually skim titles for first impressions, and click opportunistically through the postings. What if I can have a model weigh the postings and compare them to my list of current interests, to mark them for my attention? In aid of that one specific reading intention.

That’s what the first experiment does: label postings that seem to fit my interests, and express why. So that I can skim the folder of weak ties by interest, and read those items first if my intention is to explore those interests. I limited it to the c150 folder as feeding all rss feeds into the model is consuming a lot of time and tokens, so I started with the part most likely to bring useful results.
The labeling works now as part of my feedreader. I am not yet convinced of the quality of it though. The motivation for the labels usually is along the lines of "it fits interest X but not in the way you’re looking for", which to me means it actually doesn’t really fit.

Slopsidian
This week I read an article about AI documenting its own actions and output in a wiki, and saw one or two similar efforts described. I applied that to a different helper task, which is the preparation of reading a paper and helping me to decide to dig deeper. This is similar to skimming a non-fiction book, but more involved. Can AI reliably pull from a paper the concepts used and introduced, and the line of argumentation? Saving them both in a single note for the resource, and in separate notes for each of the concepts? Additionally can it logically link concepts from different resources? This is what an ‘ingestion skill’ now does for me. I let it store the output it generates in a folder that I can also open as an Obsidian vault, hence the name Slopsidian. The papers come from my Zotero collection, meaning I previously saved them. That original step of curation also means I have a line or two about why I thought them interesting at the time. Feeding that curating decision and the paper into the ingestion skill allows a second order look at a paper. What are the concepts discussed, and, reading the output, do I think some of those are of interest to me? If so, I can look at the paper more closely and do my own note making and paraphrasing and placement in my actual Obsidian collection. Lifting out concepts works rather well, the linking is less useful in the first experiences (too obvious, not sparse enough) and can seem forced when you look at why some concepts get linked.

WittgenstAIn III
The third experiment is a bit more on the edge I think. Here the probabilistic language games that LLMs are have more of a free rein. Part of the university courses on philosophy of science I did 25 years ago was using different philosophical schools of thought as lenses to approach a question. Not to answer the question, that is hardly ever the point after all, but to holding it, and holding it differently. Plato’s essentialism, Kant’s transcendence, dialectics (Hegel), phenomenology (Husserl), Wittgenstein II’s analytical method, hermeneutics (Heidegger), deconstruction (Derrida), and Rorty’s pragmatism. For each of these, for over 2 decades, I’ve had a recipe in my notes to apply to a question.
I put together a ‘language game’ in which I pose a question, which a ‘router’ prompt tries to match to one or more of the 8 recipes, or to a combination of recipes chained together (e.g. first look at a question from an analytical perspective and then feed the results in to a deconstruction exercise.)
My existing multi-step recipes are followed, and output is generated for each of those steps, into a resulting note.
I read those resulting notes, lift out what catches my eye or what resonates and I use it to flesh it out more, for me to hold the question still longer. Models are language games of a sort, so hence the name WittgenstAIn III, a third iteration, extending the second Wittgenstein’s language games to and with AI.
The output here makes me more uncomfortable than the other two. Reasoning is being mimicked, with the usual overconfident wrongness we’ve come to expect from generative AI, and that works out in odd ways sometimes. Still there is utility that can be lifted from the output. It is a good kickstart for exploring questions to quickly see if a recipe might yield something or not, judging by my first attempts in this experiment. It does certainly lower the threshold, as helper task, to engage with the recipes. I’ve used it more in the past days than in the past months. Part of that is the novelty of the experiment, and that may wear off quickly, but perhaps it carries the kernel of more habitual use.

Favorited Headless Everything For Personal AI by Matt Webb

I see this being adopted around me too. Not just CLI’s though, also more APIs, pulling in data sources from elsewhere. And most interestingly: I see adoption by people who did not program or treat their computer as their personal toolbox they can adapt before. Until generative AI lowered their barrier to entry. Going from 0 to using the command line (which coincidentally is what it was until 30 years ago anyway). Even without AI, CLI tools, like Automator on Mac did before, allow the creation of workflows around a piece of software. Matt mentions the Obsidian CLI, and I’ve been using that to manipulate Tasks in Obsidian without going to the Obsidian UI. For about a decade I’ve treated application UIs as just views on my data, with functionality geared towards the viewing, and interfaces as different queries on that data. Going headless means removing the viewer, and using the output of queries directly programmatically. Combined with how I see the arch of generative AI bending significantly towards deterministic code, I look forward to the type of things people come up with. Not their tools, but what they come up with. Because the path to scale of these things imo is not adopting or buying what someone else made, but adopting what someone else came up with conceptually and creating your own local version. Like we do socially too, contagion spreading through effective behaviour, and culturally, the contextual and local sum of all time greatest hits of our group behaviour. The invisible hand of networks rather than markets. It would be highly ironic if unethical corporate extractive AI not only creates the incentive but also actually paves the way for the masses to Walkaway.

It turns out that the best place for personal AIs to run is on a computer. […] ideally your computer. That way they can see the docs that you can see, and use the tools that you can use, and so what they want is not APIs (which connect webservers) but little apps they can use directly. CLI tools are the perfect little apps.

Matt Webb

Favorited AI Policy and Human.json by Claudine Chionh
Favorited Adding human.json to WordPress by Terence Eden

Claudine Chionh and Terence Eden both mention human.json, a data file that lists people and sites you know are written by humans, as opposed to generated by AI. A rekindling of FOAF?

In these days of needing to assume anything you encounter is machine generated unless proven to be human made, we continuously have to apply a Reverse Turing test: do I have enough indications to assume something was created by a human.

When I first wrote a Reverse Turing page I mentioned much the same things as Terence Eden does about vouching for other people to be human authors.

Not sure if having a machine readable file makes the right point here though, ironic as it is. Blogrolls, webrings come to mind too, because Long Live the Author.

One element I think we’d need to contemplate is to not just list, but also provide URI’s to some supporting evidence. Expose the depth of a connection. Only met at a vouching party countersigning your credentials, or two decades of in person and online encounters and proof thereof are different in depth and quality, and may well impact how the Reverse Turing test turns out for others perusing your human.json file.

Favorited I used AI. It worked. I hated it. by Michael Taggart

An excellent post by Michael Taggart on how it felt to him to make a much needed bit of code with the help of Claude Code. The results worked, but he hated how it made him feel. He explores those opposing outcomes without trying to resolve the tension. Much in here that I recognise from my own experiences, as well as what I see others do and how they talk about it. Towards the end he talks about ‘the real monster’ here, and I think that is the right frame: we have created a technology monster once more, and Smits’ monster theory (2003) is a tool to bring to bear again. Where will we adapt the monster to our tastes? Where will we shift our cultural understanding of ourselves and the world to make room for the monster? Once we’re done embracing it until the bubble bursts, or rejecting it outright no matter what.

I hated writing software this way. Forget the output for a moment; the process was excruciating. Most of my time was spent reading proposed code changes and pressing the 1 key to accept the changes, which I almost always did. I was basically Homer’s drinking bird.

Michael Taggart

Favorited If you thought the speed of writing code was your problem – you have bigger problems by Andrew Murphy

Good blogpost on how ‘speeding up’ code production (x lines committed this week, yay!) by using AI, will likely cause more trouble in an organisation. Because the theory-of-constraints bottleneck in an organisation will never be the speed and volume of writing code.

For non-coders making personal tools, this is I think different.

When you optimise a step that is not the bottleneck, you don’t get a faster system. You get a more broken one.

Andrew Murphy