A setup guide · Obsidian + Claude

Christiana’s writing, searchable.

Step by step, from a blank laptop to a private library of every Word and Google Doc you’ve ever written — one you can search, sort by date or topic, and ask questions of in plain English. No coding, nothing to install beyond two apps. About an hour of setup, then Claude does the heavy lifting. Every prompt on this page has been run end-to-end on a test archive.

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Click a step’s number to mark it done — this page remembers.

Read first · 3 min

What you're building, and what you'll need

You’re setting up three things that work together. Once they’re connected, you mostly just talk to Claude.

Obsidian

A free app that shows a folder of plain-text files as a beautiful, searchable library. This is where you'll read and search your writing.

Claude (Code)

The AI. It runs on your laptop, reads that same folder, and does the work — converting files, organizing, tagging, answering questions.

The Vault

The folder itself, pre-organized with numbered subfolders and instructions that teach Claude how to file and connect things. It's yours; it lives on your computer.

You’ll need

  • A Mac or Windows laptop. This guide is written for Mac; Windows differences are called out where they matter.
  • About an hour for setup, plus time to let Claude work through your files (it can run while you do something else).
  • A Claude subscription. Pro (~$20/mo) is fine to start. If you have hundreds of documents, the people who built this system recommend bumping to Max (~$100/mo) for the first heavy month, then dropping back down.
  • Your Word documents, and access to the Google account that holds your Google Docs.
Why:The one idea to hold onto: the vault is a plain folder on your computer. Obsidian shows it. Claude works in it. Both point at the same folder. Nothing lives in a company’s cloud — if you stopped using either app tomorrow, your files would still be right there.

Phase 1 · about 20 min

Install the three apps

Nothing here needs a terminal. Download, open, sign in.

Create a Claude account and pick a plan

5 min

Go to claude.ai and sign up with your email. Then choose a plan — Pro is enough to get going. You can change plans any time.

Download the Claude desktop app

5 min

This is the app you’ll talk to. Download it, drag it to Applications, open it, and sign in with the account you just made.

Once you’re in, look at the top of the window: there are tabs like Chat, Cowork and Code. You’ll be using Code — that’s the version of Claude that can open a folder and work inside it.

Note:Don’t worry about “Claude Code” sounding technical. It’s the same Claude — it just knows how to work with files. You’ll never type a command yourself; you’ll ask Claude to.

Download Obsidian

3 min

Free, no account needed. Download, drag to Applications, open it once. If it offers Obsidian Sync or a paid plan, skip — you don’t need them.

Python and git — nothing to install, but read this

1 min

The vault uses two small helpers that come with your computer: Python (for the conversion) and git (the undo history). On a Mac you don’t install anything. But the first time Claude uses one of them, macOS may show a pop-up:

If you see “…requires the command line developer tools. Would you like to install the tools now?”:Click Install, agree to the license, and wait — it takes 5–10 minutes and installs quietly. When it finishes, tell Claude “done, try again.” This happens once per computer, and only on Macs that have never been used for anything technical.

On Windows, install Python from python.org (tick Add python.exe to PATH on the first installer screen) and Git for Windows — the Claude app’s Code tab needs it. If either goes wrong, don’t fight it: in step 8 you can tell Claude “install it for me.”

Phase 2 · about 20 min

Set up the vault and connect both apps to it

You’ll download a ready-made folder, put it in Documents, then open it in Obsidian and in Claude. One thing to know up front: the download is a folder with a folder inside it. Obsidian opens the inner one; Claude opens the outer one. Both steps below say exactly which.

Download the vault kit and put it in Documents

5 min
  1. Click the download button below. A file called creator-system-main.zip lands in your Downloads.
  2. Double-click the zip to unzip it. You get a folder called creator-system-main.
  3. Drag that folder into your Documents folder.
  4. Rename it to something that’s yours — this guide calls it Writing Vault. (Click the name once, wait a second, type, press Return.)

Open it and look inside. You’ll see:

  • a folder called vaultthis is your library: numbered folders 00_HOME, 01_INBOX, 02_SOURCES and so on. Your writing will live in here.
  • a folder called tools, and a few guide files like RECIPES.md — helpers and manuals for Claude.

Leave everything exactly where it is.

Why:The kit is the open-source Creator System — a folder structure plus a set of instructions and skills for Claude, released free under an MIT license. It’s what makes Claude behave like a careful archivist instead of a chatbot.

Open the inner “vault” folder in Obsidian

3 min
  1. Open Obsidian.
  2. On the welcome screen click Open folder as vault (or the Open button next to it).
  3. Navigate to Documents → Writing Vault → vault — click the inner folder called vault — and click Open.
  4. If Obsidian asks about “restricted mode” or trusting the author, choose Trust author and enable plugins. The kit is open source and safe. (It may not ask at all.)

You should now see the numbered folders down the left side. Click 00_HOME → Start Here to have a look. Don’t worry about understanding it all yet.

Why the inner folder:The kit’s Obsidian settings live inside vault, and the links Claude writes between pages assume vault is the top. Open the outer folder instead and those links won’t connect.
Tip:Two Obsidian shortcuts worth learning now: +O opens any file by name, and ++F searches the text of every file in the vault. (Windows: Ctrl instead of .)

Open the outer “Writing Vault” folder in Claude

3 min
  1. Open the Claude desktop app and click the Code tab at the top.
  2. In the area where you type, there are a few settings. Make sure Environment is Local. Then click the Project folder selector and choose Documents → Writing Vault — the outer folder this time, the one that contains vault and tools.
  3. You’ll see “Writing Vault” shown near the chat box. That means Claude is standing inside your folder.
Two different folders — on purpose:Obsidian: the inner vault. Claude: the outer Writing Vault. Claude needs the outer one so it can see its own instructions and tools; Obsidian needs the inner one so page links work. Every time you come back, check that Claude is on the Code tab with Writing Vault selected — it only sees the folder it’s pointed at.

Say hello, then type “let’s go”

10 min

First, a quick safety habit that the kit’s own author recommends whenever you download something onto your computer:

Paste this into Claude
I'm not technical and this is my first time here. Please read through this whole folder and tell me, in plain English, what it is and what it does. Is there anything in it that could harm my computer or send my files anywhere? Keep it short.

Read the answer. Then start the built-in setup by typing exactly:

Paste this into Claude
let's go

Claude now walks you through a short conversation, one question at a time. Here is what it will ask and what to say. Use your own words — these are just shapes:

  1. “What’s your name, and what do you do?” — e.g. “My name is ___. I’m a writer — essays and personal nonfiction. This vault is going to hold about fifteen years of my writing from Word and Google Docs so I can search it and find the themes.”
  2. “What raw material do you have?” — e.g. “Mostly Word documents and Google Docs — hundreds of essays and drafts. Not much else.”
  3. “Drop ONE file into the inbox and I’ll ingest it.” — this is the one place to steer it. Don’t drop a single file; paste this instead:
Paste this into Claude
I'm going to bring my whole archive in as one big batch in a moment, following a guide. Please skip the single-file step, set up git now, and tell me when you're ready for the batch.

Claude sets up git (the invisible undo history for the whole folder — it means nothing you do later is unrecoverable) and says it’s ready. That’s the end of setup.

About permission pop-ups:Claude asks before it changes anything on your computer — you’ll see prompts like “Allow Claude to edit this file?” or “Allow Claude to run this command?”. During setup and ingesting, it’s fine to allow them; that’s the work you asked for. If one ever confuses you, just type “What is that going to do?” before you click.
If a macOS window pops up about “command line developer tools”:That’s the one-time install from step 4. Click Install, wait for it to finish, then tell Claude “done, try again.”

Phase 3 · 15 min of clicking, then waiting

Gather your writing into one place

Goal: one folder on your Desktop called My Writing with everything in it. It does not need to be tidy — Claude sorts it.

Word documents → one folder on your Desktop

10 min

You are collecting copies, not moving anything. Your originals stay exactly where they are. It doesn’t matter how many there are — 40 or 4,000 — and it doesn’t matter how messy the names or folders are.

  1. On your Desktop, right-click an empty spot → New Folder. Name it My Writing. Open it and make a folder inside called Word.
  2. Find every Word file on the Mac in one go: open a new Finder window, press +F. In the search bar that appears, make sure This Mac is selected (not just the current folder). In the row of filters, change KindDocument, and in the box beside it choose Word. The list fills with every Word document on the computer.
  3. Click any file in the list, press +A (select all), then +C (copy).
  4. Open Desktop → My Writing → Word and press +V (paste). Wait for the copy to finish — a progress bar shows for large batches.
  5. Files on an external drive, in a Dropbox/OneDrive/iCloud folder, or attached to old emails? Repeat: find them, copy, paste into the same Word folder. Duplicates are fine.
  6. Note the count. Click once on the Word folder and press +I. Under “General” it says how many items are inside (e.g. 2,314 items). Write that number down — in step 12 you’ll check it against Claude’s count. (Finder counts folders and non-Word files too, so expect “close”, not exact.)
Old .doc files:Word files from before ~2007 end in .doc instead of .docx. Include them — Claude handles the conversion in step 13. You don’t need to do anything different.
Files with a little cloud icon:If a file shows a cloud symbol next to its name, it lives online (iCloud/OneDrive “optimize storage”) and isn’t on the disk yet. Copying it triggers a download; give the paste time to finish before moving on. If a batch seems stuck, wait a few minutes rather than cancelling.
On Windows:In File Explorer, click in the search box (top right) and type kind:document ext:docx OR ext:doc. Select all (Ctrl+A), copy, paste into My Writing → Word.

Google Docs → download them all with Google Takeout

10 min + waiting

Google Takeout packages up your whole Google Drive as a zip. It’s the reliable way to get years of Docs out at once.

  1. Go to Google Takeout. Even if you’re already logged in, Google shows a Verify it’s you screen and asks for your password again — that’s normal for Takeout. Sign in to the account that has your Docs.
  2. Click Deselect all at the top of the list.
  3. Scroll to Drive and tick its box.
  4. Click the Multiple formats button under Drive. Make sure Documents is set to DOCX (the default). Click OK.
  5. Optional: click All Drive data included (may just say All data included) to pick only the folders that hold your writing. If your writing is everywhere, leave it.
  6. Scroll to the bottom, click Next step.
  7. Leave “Send download link via email” and “Export once” (a one-time archive). Set file size to 4 GB so it comes as fewer zips. Click Create export.
  8. Wait for the email (minutes to hours depending on how much you have). Download the zip(s), double-click to unzip, and drag the resulting Takeout folder into My Writing — rename it Google.
Only a handful of Docs?:Skip Takeout. Open each Doc, then File → Download → Microsoft Word (.docx) (or Markdown (.md), which is even better) and drop the files into My Writing → Google.

Drop the whole folder into the vault’s inbox

2 min

The vault has an “in tray” folder called To Process. Everything Claude works on starts there. It’s buried a few folders deep, so let Obsidian open it for you instead of hunting for it:

  1. In Obsidian’s left sidebar, expand 01_INBOX and right-click the To Process folder.
  2. Choose Show in system explorer. A Finder window opens with To Process highlighted. (Don’t see that menu item? No problem — in Finder go to Documents → Writing Vault → vault → 01_INBOX → To Process by hand.)
  3. Double-click To Process so you’re inside it (the window will look empty or nearly empty — that’s right).
  4. Drag the My Writing folder from your Desktop into that window. It moves off the Desktop and into the vault. Done.
  5. Look at Obsidian: My Writing now shows under 01_INBOX → To Process. The Word files inside won’t open in Obsidian yet — it only reads plain text — which is exactly what the next phase fixes.
Thousands of files? Do it in rounds:Everything works with one giant folder, but if you have more than ~500 documents you may find it calmer to drag in one chunk at a time — for example Word first, run the prompts in Phase 4, then come back and drag in Google. The conversion prompt in step 13 is safe to run again and again: it only touches what’s still in the inbox.

Phase 4 · Claude works, you supervise

Bring the writing into the vault

Four prompts, in order. Copy each one into Claude (Code tab, Writing Vault selected), press Enter, and let it run. Read what it reports back before moving to the next. Every one of these has been run end-to-end on a test archive; they work without installing anything.

One setting first: next to the send button there’s a mode selector (it probably says Manual). Switch it to Accept edits for this phase. Claude will still ask before running commands, but won’t stop for every single file it writes — otherwise you’d be clicking Allow hundreds of times.

Prompt 0 — check that everything arrived

Claude: 1 min

Before converting anything, have Claude count what’s in the inbox and compare it to the number you wrote down in step 9. This catches a half-finished copy or a folder dropped in the wrong place before an hour of work is built on it.

Paste this into Claude
Look inside vault/01_INBOX/To Process/My Writing and tell me what's there. I want:
- for the Word folder and the Google folder separately: how many .docx files, how many .doc files, and how many other files (by type)
- the total number of Word documents overall
- the oldest and newest file dates you can see
Don't change, move, or convert anything yet — just report.

Does the Word folder total roughly match your Finder count from step 9? A few off is fine (Finder counted the folder itself and any stray files). If it’s way off, the copy probably didn’t finish or the folder went somewhere else — tell Claude: “I expected about 2,300 Word files. Help me figure out where the rest are.” If it matches, carry on.

Prompt 1 — convert everything to plain text and file it

Claude: 10–90 min

Word and Google files are locked-up formats. This asks Claude to turn each one into a plain-text Markdown file (which Obsidian can search) while keeping every original untouched — using only what’s already on your Mac. It’s the longest-running step; the batch reports let you watch it move.

Paste this into Claude
In vault/01_INBOX/To Process/My Writing there are Word documents (.docx, and possibly older .doc files) and a Google Takeout export of my Google Docs (also .docx). This is years of my writing.

Please:
1. Convert every document to a Markdown (.md) file. Use only tools already on this Mac — textutil (built in) converts .doc and .docx, and you can write a small Python script if you need to. Do NOT install Homebrew or anything that would ask me for a password. If you truly can't proceed without installing something, stop and tell me what and why first.
2. Do a dry run first: show me the plan (how many files, where they'll go) and wait for me to say "go" before moving anything.
3. Keep each file's original filename as the title (just change the ending to .md). Keep headings, paragraphs AND line breaks — some of these are poems, and a line break inside a stanza must stay a line break (in Markdown that means two spaces at the end of the line). Test this on a poem before doing the whole batch.
4. At the top of each .md file add frontmatter with: title, date, date_source, word_count, source (word or google), and original_path. For the date: use a "Written ..." line or a clear date near the top of the text if there is one; otherwise the document's own date. In date_source just say in plain words which you used (e.g. "Written line in the text" or "file date").
5. File the .md files in vault/02_SOURCES/Writing/, in subfolders by year. If the only date you can find is a file date from this year (that's just when I copied it), treat it as undated and put it in vault/02_SOURCES/Writing/undated/. If two files would get the same name in the same year, add (2), (3) — never overwrite.
6. Move the untouched originals into vault/02_SOURCES/Writing/_originals/ (keep their folder structure) so nothing is lost. Never modify or delete an original.
7. Anything that isn't my writing (spreadsheets, PDFs, images, web pages) — move it to vault/01_INBOX/To Process/_skipped/ and list it for me.
8. Work in batches of about 25 files and give me a one-line progress report after each batch, like: "Batch 3 done — 75 of 2,314 converted." (If I only have a few dozen files there'll only be a couple of lines — that's fine.)
9. Save the script you write in tools/ so we can run it again later. If I run it again with new files in the inbox, only process what's still in the inbox — never redo files already in 02_SOURCES/Writing/.

When you're done, tell me: how many files you converted, how many you skipped (and list them), any you couldn't read, and confirm the My Writing folder is now empty. Then save an undo point with git.
While it runs:Claude shows the plan and waits for you to type go. Then leave the app open and go do something else. If it stops to ask a question, answer it and it continues. If it stops without finishing, type “keep going”. If it says it hit a usage limit, wait for the reset time it gives you, then “keep going” — it picks up where it left off, because it only processes what’s still in the inbox.
How you know it worked:In Obsidian, expand 02_SOURCES → Writing. You should see year folders, and inside them your pieces as ordinary readable notes. Click one. If it opens and reads like your document, you’re done. The Word originals are safe in 02_SOURCES → Writing → _originals — they didn’t disappear, they moved.
Poems: check one now:Open a poem in Obsidian. Are the lines still separate lines? If two got squashed into one, tell Claude: “Some poem lines merged. Fix the converter so soft line breaks are kept, and redo just the poems.” (This happened once in testing; Claude fixed it in one go.)
Want folders by kind — Poems, Essays, Journal?:Now is the moment, before the index. Jump to section 7 and run the “sort by kind” prompt, then come back to Prompt 2.

Prompt 2 — build an index of every piece

Claude: 10–30 min

Now you have hundreds of clean files. This creates one page that lists all of them with dates, topics, and a one-line summary — the table of contents for your life’s writing.

Paste this into Claude
Read every file in vault/02_SOURCES/Writing/ and build a page at vault/00_HOME/Writing Index.md.

Make it a table with one row per piece: title (linked to the file), date, word count, topic tags, and a one-sentence summary of what it's about. Sort newest first.

Also add a "tags:" list to each source file's frontmatter — that's fine, it's metadata at the top of the file, not my text. Use a small, consistent vocabulary of about 15 tags total: each piece gets its main subject plus whatever else genuinely applies (usually 2–5). Reuse the same tag names rather than inventing new ones. When you're done, show me the full list of tags with how many pieces have each one, and save an undo point with git.

Open 00_HOME → Writing Index in Obsidian. This is your library catalogue. It’s a normal file — you can edit any line.

Prompt 3 — let the vault find your themes

Claude: 15–45 min

This is where it stops being a filing cabinet. The kit ships with skills for exactly this: diarize builds a page about one subject from every source that mentions it; emerge looks for patterns nobody named.

Paste this into Claude
Using the Writing Index and the tags, tell me the 10 subjects I write about most often across all my writing, with a rough count and date range for each. (Subjects — not recurring phrases or people's names, unless a person really is the subject.)

Then, for the top 5, run the diarize routine (vault/.claude/commands/diarize.md) on each one to build a canon page in vault/04_CANON/Practice/Themes/ — the vault's usual place for themes. Skip the web-search step; these are my private essays. Each page should describe the theme, how my thinking about it changed over time, and quote or link the specific pieces where it shows up. Every claim should link back to a source file.

Finally, run the emerge routine (vault/.claude/commands/emerge.md) once and tell me what patterns you found that I might not have noticed. Then save an undo point with git.
Why:The vault has a rule: sources are never modified; synthesis lives on separate pages and always cites its sources. So the theme pages Claude writes are its reading of your work, clearly labeled — your original words stay untouched in 02_SOURCES.

Phase 5 · everyday use

Search, sort, and find topics

From here on there are two ways to look through your writing. Use whichever suits the moment.

Searching in Obsidian (instant, visual)

ongoing
  • ++F — search the words inside every file. Results show the matching lines; click to jump.
  • +O — jump to any file by typing part of its title.
  • Click a tag (like #grief or #travel) anywhere and Obsidian lists every file with that tag.
  • In the file list, right-click the Writing folder → sort by name or by date.
  • +G — the graph view: every file as a dot, every link as a line. Your themes show up as clusters.

Asking Claude (when you want thinking, not just matching)

ongoing

Open Claude (Code tab, Writing Vault) and ask in ordinary language. It reads the relevant files before answering, and it can make new pages for you. Some starters:

Examples — pick one, or write your own
Find everything I've written about my father. Give me the passages, with a link to each file and its date.

Which pieces from 2018–2021 are about work? Sort them by date and give me one line on each.

Show me my ten longest pieces and my ten shortest.

I think I've written about "leaving" a lot. Am I right? Where, and how did the way I wrote about it change?

Make a page that groups all my writing into 8 themes, with the pieces listed under each.

Pull the best three paragraphs I've ever written about New York into one file so I can reread them.

I want to write a new essay about X. What have I already said about it, and what haven't I said yet?

Two habits that keep the vault healthy, straight from the kit’s authors:

At the end of a working session:

Paste this into Claude
Write a recap of this session to the log — the recap routine (vault/.claude/commands/recap.md). Then save an undo point with git.

Claude writes a dated note of what changed at the top of 00_HOME → Log, so next time you can ask “where was I?”

About once a week:

Paste this into Claude
Run the vault health check — the vault-lint routine (vault/.claude/commands/vault-lint.md). Tell me which findings are real problems versus template noise, and fix the 3 real ones. Then save an undo point with git.

It checks for broken links, duplicates and stray files. The first run always finds a lot; most of it is scaffolding, which is why the prompt asks Claude to sort real from noise.

New writing:Whenever you finish a new piece, drop the file into 01_INBOX/To Process and tell Claude “new piece in the inbox — convert it, file it, and update the Writing Index.” The library keeps growing.

Phase 6 · read when needed

When you get stuck

Rule zero: ask Claude

It can see the whole vault, so it’s a better troubleshooter than any help page. Say exactly where you are, even if that’s “I don’t know what to ask.”

Paste this into Claude
I'm stuck and I'm not technical. Explain to me like I'm brand new: what state is my vault in right now, and what should I do next? Give me 2 or 3 options and tell me which one you'd pick.
Paste this into Claude
Something went wrong and I want to undo what just happened. Use git to show me what changed in the last hour, and put it back the way it was if I say so.

Common snags

  • “Command not found” / git or pandoc missing — tell Claude: “install it for me.”
  • Claude says it can’t see the folder — you’re on the wrong tab or the wrong folder. Code tab, Writing Vault.
  • Word files won’t open in Obsidian — expected. Obsidian reads the .md copies Claude made in 02_SOURCES/Writing.
  • Claude hits a usage limit mid-ingest — wait for the reset, or bump the plan for a month. Ingesting a big archive is the most expensive thing you’ll ever ask it to do; everyday use is light.
  • Too much, too fast — the kit’s advice: five documents is enough to try everything. Do a small batch first if the full run feels overwhelming.
  • “Where did my Word files go?” — they moved, they didn’t vanish: 02_SOURCES → Writing → _originals. Anything Claude decided wasn’t writing is in 01_INBOX → To Process → _skipped.
  • Claude keeps asking me to drop one file — that’s the built-in onboarding. Paste the “skip the single-file step” line from step 8.
  • Page links look broken in Obsidian — you probably opened the outer folder. Close it and open the inner vault folder instead (step 6).

Privacy, plainly

The vault is a folder on your laptop; nothing syncs anywhere unless you set that up. When you ask Claude something, it sends the relevant files to Anthropic’s servers to think about them and then they’re gone — same as pasting text into any AI chat. The kit’s own rule of thumb:

  • Fine: essays, drafts, journals, work writing.
  • Keep out of the vault: passwords, bank or card details, medical records, other people’s private information.

Good first-week prompt: “Scan my vault for anything that looks like a password, account number or private ID and tell me where it is.”

Go deeper

In the outer Writing Vault folder are three guides written by the kit’s authors — double-click to read, or ask Claude “show me RECIPES.md”: RECIPES.md (24 things to try, each with input → prompt → result), Standard Operating Procedure.md (daily and weekly routines), and Data Sources to Gather.md (what else you could bring in — photos, email, old chats).

Phase 7 · what it can and can’t do

Organizing your writing, and searching the deep past

Once the writing is in, this is what to ask for, what to expect back, and where the edges are. Everything here was tried on a test archive of essays and poems.

Who does what

Obsidian doesn’t read or sort anything — it’s the window and the search box. Claude does the reading: it can open every piece, decide what it is and what it’s about, make folders, add tags, write pages, and answer questions. Anything Claude organizes shows up in Obsidian a second later, and you can drag things around yourself if you disagree with a call.

The one design idea to hold onto: folders for kind, tags for theme. A piece is one thing (a poem) but about many things (your mother, Brooklyn, leaving). Folders can only hold a piece in one place; tags can mark it with ten. So kinds become folders, and themes become tags plus theme pages.

Folders by kind — Poems, Essays, Journal, Drafts

Best run right after Prompt 1 (before the index), but it works any time — Claude updates the links if pages already point at the files. Change the list of kinds to whatever fits your writing.

Paste this into Claude
Sort my writing by kind. Read every file in vault/02_SOURCES/Writing/ (not _originals) and decide what each one is: Poem, Essay, Journal, Draft, or Other. Rules: judge by the writing itself, not just the filename. If a piece is a poem that's also a draft, it goes in Poems (kind: Poem, plus a "status: draft" line) — kind wins over status. Anything you're not sure about, tell me and take your best guess.

Then move each .md into a subfolder by kind — vault/02_SOURCES/Writing/Poems/, Essays/, Journal/, Drafts/, Other/ — keeping the year folder inside (e.g. Poems/2015/Kettle.md). Add a "kind:" line to each file's frontmatter. Leave _originals exactly where it is. If any page in the vault links to a file you moved, update the link.

Also update the import script in tools/ so that next time I bring in new files it sorts them by kind the same way.

When you're done, show me the counts per kind and the list of anything you weren't sure about, then save an undo point with git.

In testing, Claude sorted 44 pieces into Essays 34 / Poems 5 / Drafts 5 in one pass, explained its reasoning (poems: short, lineated, stanza breaks; essays: prose paragraphs), and listed four borderline calls for the writer to decide. That “not sure” list is the part to read.

Themes — tags and theme pages

Prompt 2 already tags every piece and Prompt 3 builds theme pages for the top five. From there:

  • See everything on a theme, instantly: in Obsidian, click any tag (e.g. #grief) — or open the Tags pane on the right — and every piece with that tag lists, across all kinds and years. That’s your “folder” for a theme, without moving anything.
  • More theme pages: “Build a theme page for #brooklyn the same way you did the others.”
  • A theme you name yourself: “I think there’s a thread about silence in my work that no tag captures. Read everything, find it, tag it #silence, and write me the page.”
  • Re-tag with your own vocabulary: “Rename #new-york to #nyc everywhere and merge #brooklyn into it.”

What you can ask — real examples

All of these work today. Claude searches for likely words, reads the candidates, and answers with links you can click straight into the file.

Finding things
Find everything I've written about my mother. She's "Mom", "Ma", "my mother", and sometimes just "the kitchen". Give me the passages, each with a link to the file and its date, oldest first.

Which pieces from 2012 to 2016 mention the apartment on Graham Avenue?

I wrote a paragraph once about a letter I never sent. Find it — it might be in an essay or a poem.

Show me every poem that mentions light. Which image comes up most often across the poems?
Sorting and comparing
List my essays longest to shortest with word counts.

Which years was I most productive? Give me a table: year, number of pieces, total words.

I have three versions of "The Pitch". Show me the differences between them and tell me what changed in how I told it.

Group all my journal entries by season and tell me what I tend to write about in winter versus summer.
Seeing patterns
How did the way I write about leaving change between my twenties and now? Quote the evidence.

Which people appear across the most pieces? Make a page for each of the top five with every place they show up.

Read all my drafts. Which three are closest to finished, and what would each need?

I want to write a new essay about running. What have I already said, and what haven't I said yet?
Making things from it
Pull my best three paragraphs about New York into one file so I can reread them together.

Make me a chronological reading list of everything about my father — a page with links, one line on each.

Draft a 300-word bio of me as a writer, using only what's actually in the vault. Cite the pieces you drew from.

The honest limits

  • Claude searches by words first, then reads. It does not have a magic index of every sentence. If you ask about your mother and a piece only ever says “the woman who raised me”, a quick search will miss it. Two fixes: give Claude the aliases (as in the example above), or ask for an exhaustive pass — “read every piece from 2010 to 2015 in full and…” — which is slower and uses more of your plan, but is thorough. For a few hundred pieces this is fine; for thousands, ask a year-range at a time.
  • The better the index and tags, the better the deep search. Claude uses the Writing Index, tags and theme pages as its map. If searches feel thin, ask: “Add a two-sentence summary to the top of every piece” or “tag every piece with the places it mentions.” Each pass makes the next question sharper.
  • Obsidian’s own search is exact. ⌘⇧F finds the word father, not dad. It’s instant and never wrong about what it finds — use it when you know the word. Use Claude when you know the meaning.
  • Claude’s memory is the vault. Each session starts fresh; it remembers only what’s written in files. “The piece I asked about yesterday” works only if yesterday’s recap is in the log — hence the recap habit. The upside: nothing is locked inside a chat; it’s all in plain files you own.
  • Repeated refrains count as many hits. If you reuse a passage across pieces, a “find everything about X” will surface it each time. Say “show me one instance per piece” if that’s what you want.
  • Versions aren’t merged. The same essay in Word (2016) and Google Docs (2025) becomes two files. That’s correct — but ask “mark older versions of the same piece as superseded” if you want the noise reduced.
  • Old-file quirks. A very old Word file can carry odd characters (an em-dash that shows as —). Claude will flag these; “fix the odd characters in that file” handles it.
  • Cost. Filing and indexing hundreds of pieces is cheap. Asking Claude to read everything to answer one question is where usage goes. Fine on the Max plan; occasionally limit-hitting on Pro — it tells you when, and “keep going” resumes after the reset.