I recently published an annotated AI-generated essay, Claude finds Contradictions in My Thinking, which found some interest on Hacker News. Basically, I let Claude loose on two of my Obsidian vaults: one has been gathering dust with my very early yet dense collection of notes and a more recent vault where I publish this site from. As this is a second write-up on Claude exploring my Obsidian and I think there will be some more of this kinda reflection, I will call this the Claubsidian essay series.

So far, I have thought of three reasons for unleashing Claude in my Obsidian vaults. The first and main reason is that I wanted to see what contradictions Claude can uncover in my thinking over 5-ish years of note-taking and to see if any of these were something I didn’t know about myself. My annotations in the first essay indicated that Claude is decent at articulating contradictions but none felt novel to me. The second was to get suggestions for new essays from Claude — this would allow me to convert my fleeting notes into something complete and coherent while also trimming the fat from my note collection. This also allows me to see if any of these suggestions are any good or resonant with my current sentiments —. a good reason to delete those notes perhaps. And the last reason is that even if I don’t convert any of Claude’s suggested essays, it might still allow me to update my old notes in a more manageable manner and perhaps link them to the newer notes that have been becoming essays. The preceding two reasons should also help me overcome the cold start problem with reviewing my older notes as I either get lost in them despite putting in considerable effort to index them à la Luhmann. The indexing of this earlier set of notes can be seen here for anyone interested—I have Claude reference specific notes from this site.

The below are the set of prompts that I used in getting suggestions from Claude (they probably have typos that I haven’t removed or proofread here).

The below is Claude’s output after these set of prompts. What was especially nice was not having to manually replace the backlinks from Prompt 3 with the URLs of my already published notes via Obsidian Publish. That said, I am yet to evaluate the quality of the essay suggestions as I need to sit with these notes. Perhaps the quality of suggestions are not a fault of Claude but the quality and thoughtfulness of the notes themselves. Time may tell.

Revised Assessment

Your newer essays demonstrate you’ve already tackled several themes I initially identified in your Old Vault:

• Thoreau extensively covers the autonomy paradox and digital disobedience
• Graeber and Thiel explores the institutional vs. entrepreneurial tension
• Space Data Center Analysis shows your risk-taking approach to technical criticism

Given this context, here are the most promising connections for new essays:

Essay 1: “The Metascience Entrepreneur’s Dilemma”

Core published notes:

• 16 Metascience entrepreneurs work on new social processes of science
• 16a My approach to metascience entrepreneurship
• 14c How to identify risk-averse researchers
• 16c High risk high reward researchers is a misnomer
• 0f What funders can do to help academic founders

Connection to newer work: This builds on your Thoreau essay’s critique of institutional complicity and your Graeber and Thiel analysis of working within vs. outside systems. Your published notes on identifying risk-takers (“fewer publications, more prototypes”) provide concrete criteria that could form a practical framework.

Why this works: You have both personal experience (16a My approach to metascience entrepreneurship mentions Howler and teaching reforms) and systematic criteria for a genuinely useful piece for others in similar situations.

Essay 2: “The Great Groups Problem”

Core published notes:

• 9c Great Groups culture from Bennis’ in Organising Genius
• 9c1 Xerox-PARC culture
• 0c2a Great Groups and Institutions that generally do unfocused good
• 15 Great Groups are not cults
• 7c Human Qualities I like

Connection to newer work: Your Future Essays note already identifies this as expansion-worthy. The tension between 15 Great Groups are not cults (Bennis) and 9 Ben Horowitz on Organisational Cultures provides a substantive framework.

Why this works: The published notes contain rich details about PARC culture (Metcalfe’s “heaven” quote in 9c1 Xerox-PARC culture) that could ground your analysis of what actually enables breakthrough work vs. what creates dysfunction.

Essay 3: “From Ideas to Influence: A Personal Framework”

Core published notes:

• 6 Ideas
• 6d On good ideas
• 7 Autonomy is freedom from coercion
• 7c Human Qualities I like
• 16a My approach to metascience entrepreneurship

Connection to newer work: Your [[ Digital Disobedience ]] draft touches on this but remains incomplete. Could also connect to themes in Thoreau about individual action.

Why this works: The published notes contain your Newtonian metaphor of ideas as forces (from 6 Ideas), plus concrete examples from building Howler while teaching. This could become a practical guide for academic entrepreneurs.

What’s NOT Worth Pursuing

• Risk-taking essay: Your Space Data Center Analysis already demonstrates the kind of technical contrarianism you were theorizing about in 14a Risk-taking and weirdness go hand-in-hand
• Academic-industrial complex: Already covered in your Thoreau and Graeber and Thiel pieces
• Writing about contradictions: Your existing work shows intellectual evolution rather than needing resolution

Key Insight

Your published notes contain specific examples and frameworks that could flesh out themes you’ve introduced but not fully developed in your newer essays. The metascience entrepreneur piece particularly stands out because you have both personal experience and systematic criteria that could make it genuinely useful to others in similar situations.

Your Future Essays note suggests you already recognize the space technical pieces as expansion-worthy, but the metascience material might be your most distinctive contribution since it combines personal experience with institutional analysis.