Manage your Cowork context files without touching a terminal

Complete Set up your Cowork folder so Claude knows you on day one first; this lesson teaches you to maintain and edit the files that lesson created. If you completed Build your first Skill and put it on a schedule, you also have Skill files to organize into the SKILLS subfolder.

Obsidian lets you read and update your Cowork context files cleanly without touching a terminal, so they stay current instead of going stale. A terminal is the intimidating black command-line window that programmers type into, and the good news is you never open one here. Your Cowork folder runs on plain text files, and that is the source of its power: Claude reads them, writes to them, and the folder stays yours.

Here is the before and after: without the right viewer, a plain text file shows raw markdown (hashtags everywhere, asterisks around words) instead of formatted text, so you close it and never update it, and your context file slowly drifts from who you actually are. With Obsidian pointing at the same folder, you click a file and see real headers, bold text, and bullet points. You edit it like a document, save, and Cowork reads the updated version next session.

Why Obsidian, and why not something else: Obsidian is a free app that opens a folder on your disk and shows it as a tidy, searchable set of notes. You click a file and it shows real headers, bold text, and bullet points. You edit it there and save, and the file on disk is unchanged, so Cowork still reads it exactly as before.

This is the only thing that matters: Obsidian never alters how the file is stored. The other tools each break that rule.

Notion imports your files into its own database, so every time Cowork writes a new file you have to re-import. Google Docs are not plain text files, so you would convert back and forth every session. VS Code shows markdown too, but it is built for programmers and assumes you know your way around a terminal.

Obsidian reads the folder you already have, shows it cleanly, and writes back to disk without touching the format. That is why it fits this job and the others do not.

The SKILLS subfolder pattern: when you build a Skill in Cowork (covered in Lesson 3), the Skill file lands in your OUTPUTS folder by default. Move it into a folder called SKILLS inside your Cowork directory. Now Obsidian shows every Skill as a note: its name, its trigger description, and its body of instructions.

You can search across all Skills at once, find the one that is outdated, open it, change one line, and save. The file is live, so the next Cowork session picks it up. Keep each Skill note lean and matching the installed Skill: do not document the Skill's history inside the note, because the note IS the Skill.

The mid-session update pattern: you are in a Cowork session and Claude does something you want it to stop doing forever. Do not re-explain it in this session. Open Obsidian, find the relevant file (usually about-me.md or your voice file from Lesson 4), and add or change one specific line: "Remember [what you want it to remember]" or "Replace [what it does now] with [what you want] always."

Save the file, then open a new Cowork session and point it at the same folder. Claude reads the updated file and applies the change from the very first message. You prompted once, and it holds forever.

Obsidian is where you maintain your brain. Cowork is where you build. Both look at the same folder.

I just updated a line in my about-me.md file using Obsidian.

The line I changed: [paste the old text here]
What it now says: [paste the new text here]

Start a new task based on this updated identity. Do not reference the old version of this line. If you're not sure which version you read, tell me what the file says about [the topic you changed].

Starting fresh Cowork session. Folder selected: /Users/jane/Claude Cowork.

Your message: "I just updated a line in my about-me.md file using Obsidian. The line I changed said: 'I write responses in bullet points.' It now says: 'I never use bullet points unless explicitly asked. Default to short paragraphs.' Start a new task based on this updated identity. If you're not sure which version you read, tell me what the file says about formatting."

Claude's reply: "I can see in about-me.md: 'I never use bullet points unless explicitly asked. Default to short paragraphs.' Understood. I'll write everything in paragraph form from here. What are we working on today?"

The update took 45 seconds in Obsidian. It will hold for every future session without being mentioned again.

What good looks like

• Obsidian is installed and pointing at your Claude Cowork folder (you can see ABOUT ME, OUTPUTS, TEMPLATES, and any Projects folders in the left sidebar)
• A folder named SKILLS exists inside your Cowork directory, visible in Obsidian's sidebar
• You moved or created at least one Skill note into the SKILLS folder (if you have no Skills yet, create a placeholder note called 'my-first-skill.md' with a one-line description of a task you repeat weekly)
• You made at least one edit to a context file (about-me.md or your voice file) directly in Obsidian and saved it
• You opened a fresh Cowork session after saving, pointed it at the same folder, and Claude's response reflected the change you made

I want to build a SKILLS note for a task I repeat every week.

The task: [describe it in one sentence, e.g. "drafting a client status update email"]
How I currently handle it: [paste the prompt you repeat, or describe what you tell Claude each time]

Help me write a SKILLS note for this task. The note should include:
- A name for the Skill (lowercase, hyphens only, no spaces)
- A one-paragraph trigger description (what you say to invoke it, what NOT to say)
- The body instructions (the exact rules Claude should follow for this task)

Keep it under 500 words total. I'll save this note as [skill-name].md in my SKILLS folder in Obsidian.

What good looks like

• The SKILLS folder in your Cowork directory contains at least one .md note with a Skill name, trigger description, and body instructions
• The Skill note is visible and readable in Obsidian (formatted correctly, not raw markdown symbols)
• If you have an installed Skill from Lesson 3, its note in SKILLS matches the installed version; they are not out of sync
• You can search across your Cowork folder in Obsidian using Cmd+Shift+F (Mac) or Ctrl+Shift+F (Windows) and find the Skill by a keyword in its body