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How the Obsidian CEO Built His Claude AI Skills (and Why It Matters for Your Workflow)

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🎧  Jim reads this post

Look, I’ve been using Obsidian for about three years now. I’ve got thousands of notes scattered across my vault—old client projects, ideas from 2am, random research rabbit holes, meeting notes I swear I’ll organize someday. The problem is exactly what you’re experiencing: I know the stuff is in there somewhere, but finding it? That’s a different story. Last week I heard that the CEO of Obsidian just released some GitHub skills specifically designed to teach Claude Code how to actually read your vault. Not chat about it. Actually read it, understand it, work with it. That changed everything I was thinking about for 2026.

Why This Keeps Coming Up

We’re the generation that actually kept journals. We built filing systems with real intention. We labeled folders, created hierarchies, tried to impose order on chaos. But here’s the honest part: we also did all of that and then the system became so complex that it defeated its own purpose. I’ve got notebooks within notebooks. My vault has subfolders that reference other subfolders. I know intellectually that something useful is in there, but I can’t retrieve it because I can’t remember if it’s under “Projects” or “Research” or “Clients” or some three-level-deep structure I created at 11pm on a Tuesday. Claude Code couldn’t help with this before because it couldn’t actually access my files in a meaningful way. It could talk about what might be in there, but it couldn’t do anything real.

What I Actually Found Out

The Obsidian CEO built five specific skills designed to let Claude Code actually understand your vault structure. I’m talking about Claude reading your actual files, understanding how they relate to each other, and then rewriting them, reorganizing them, pulling information from them. This isn’t theoretical. You can point Claude at your entire vault and it can start working through it like a real assistant who actually knows where everything is. The skills teach Claude how to navigate Obsidian’s system, how to find files based on content, how to understand your linking structure. It’s the difference between describing a filing cabinet to someone versus handing them the keys and a map.

What surprised me is how much this opens up. I started thinking about all those meeting notes from three years ago that probably contain context I need now. Or the random ideas I jotted down that could connect to something I’m building right now. Or the client research I did that I’m half-remembering but can’t quite locate. Claude can find all of that. Not just search for it—actually read it, understand it, surface the relevant pieces.

What You Can Do With This Today

Honestly, start by just setting it up. Go grab the skills from the GitHub repo the CEO built. Get Claude Code connected to your vault. Then give it a simple task—something like “read all my notes from 2024 and tell me what ideas keep appearing” or “find every note that mentions X topic and summarize what I’ve learned.” Let it do actual work on your files. Not organizing everything at once, because that’s paralyzing. Just one real task that shows you what this can actually do.

I’ve been running some experiments this week. Asked Claude to read through my entire project vault and suggest which old ideas might actually be worth revisiting right now. It found connections I’d completely forgotten about. Last night I had it clean up a folder of meeting notes from 2024, pulling out action items and decisions I’d buried in prose. This is the kind of actual grunt work I’ve been avoiding because it requires sitting down and manually reviewing everything. Claude just does it.

For someone our age who’s spent decades building knowledge systems, this feels like finally having someone who actually respects the vault you’ve built instead of treating it like clutter. You’re not starting from scratch with some new tool. Your Obsidian vault is still your vault. Claude just gets permission to actually help you use what’s already there.

Go set it up. You’ll figure out pretty quickly what you can do with it. I did, and I’m still discovering new angles.

Watch the Full Video

I covered all of this in a short video too — sometimes it’s easier to watch than read.

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What I Recommend

If you want a head start, check out the AI toolkit I actually use — it’s what I point people to first.


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