Tool Friday #12 — Obsidian: 4 Months In, My Second Brain Won't Let Me Leave
Four months ago I closed my last Notion workspace. I’d been threatening to migrate for a year. The thing that finally did it wasn’t Notion getting worse — it was Obsidian becoming the only place my AI workflow made sense.
Every doc Claude writes for me — client briefs, blog drafts, competitive intel, agent instructions — lands in my vault. I open them, edit them, link them. I don’t copy-paste into Notion anymore. I don’t export, sync, or convert. The vault is where work happens.
TL;DR: Obsidian is a local-first markdown editor that turns your notes into a linked knowledge graph. It’s free, your data is plain files on disk, and the plugin ecosystem is where it becomes a second brain. Four months in, it’s the first app I open in the morning and the last I close at night. If you run AI agents that write docs, this is where those docs should live.
What does Obsidian actually do?
Obsidian is a note-taking app that stores everything as plain markdown files in a local folder. No cloud. No lock-in. You own your data because it’s literally sitting on your disk.
The superpower is linking. You type [[competitor-intel]] and Obsidian resolves it to the note with that name. Every link is bidirectional — the target note knows what links to it. Over months, those links become a graph. Your past work starts working for you.
| Feature | What it actually does |
|---|---|
| Local markdown files | Your vault is a folder. Open it in VS Code, iCloud, Git — it’s all .md |
| Bidirectional links | [[note]] creates two-way connections. The graph builds itself |
| Plugin ecosystem | 2,000+ community plugins. The reason Obsidian eats Notion |
| Graph view | Visualize your knowledge network. More useful than it sounds |
| Canvas | Whiteboard mode. Drag notes, draw arrows, think visually |
| Dataview | Turn notes into queryable databases (SQL-like) |
| Sync | Official $10/mo, or use iCloud/Dropbox/Git for free |
How I actually use it
My vault has 3,400 files across 25+ folders. The structure is boring on purpose: PARA-style (Projects, Areas, Resources, Archive) plus a top-level brain/ for context files my AI agents read.
Three workflows, all running right now.
1. AI agent output lives here. When Claude Code generates a client brief, a LinkedIn post, or an agent instruction file, it writes directly into the vault. I don’t review in a chat window — I review in Obsidian, with syntax highlighting, wikilinks auto-completing, and the rest of my context one backlink away.
2. Daily operations. Every morning a brief gets generated into notes/daily-briefs/brief-DDMMYYYY.md. I open it, scan priorities, check deadlines. At end of day, a closing report gets written into notes/daily-summaries/. Both files reference brain/context.md and the project files — so when I re-read a closing three weeks later, the links still work.
3. Content production. Every blog post I write (including this one) starts as a markdown file in the vault. I edit it with Templater for frontmatter, cross-link to past posts with [[]], preview with Ctrl+E. When it’s done, it gets copied to my Astro site and deployed. No format conversion. Same markdown, front to back.
What surprised me
The graph view is actually useful. I dismissed it for months as a toy. Then one day I was prepping for a call and zoomed out — every client, every agent, every framework I’ve built is a cluster. Orphan notes (nothing links to them) jumped out immediately: half were stale, half were ideas I’d forgotten. Fixing the orphans is a weekly ritual now.
Plugin quality is wildly uneven. There are ~2,000 community plugins. Maybe 20 are worth installing. The rest are abandoned, half-working, or actively making your vault worse. The signal-to-noise ratio forced me to stop browsing and commit to a handful of core plugins (Dataview, Templater, QuickAdd, Excalidraw) — and walk away from the “AI for Obsidian” plugin rabbit hole entirely.
Markdown portability is real. I moved my vault between three Macs, Dropbox, iCloud, and a Git repo without losing a single note. Try that with Notion.
My take — 4 months in
Most review posts are written in the honeymoon phase. This one isn’t. Here’s what’s actually changed.
What stuck: daily briefs, closing reports, AI agent docs, client project folders, content drafts. These are 90% of my daily volume. They’re faster, more linked, and zero-friction compared to Notion.
What I thought I’d use but don’t: Canvas for brainstorming (I just use a new markdown file), Excalidraw (my sketches are bad anyway), most Dataview queries (overkill for solo work).
What broke my expectations — in a good way: the AI layer. Four months ago I used Obsidian as Notion-but-local. Today I run Claude Code on top of the vault, Smart Connections surfaces stale ideas, and my AI agents read brain/context.md before every task. The vault isn’t storage — it’s the interface between me and my agents.
What broke — in a bad way: mobile UX is still janky. Obsidian on iPhone is usable for reading, painful for editing. Collaboration with non-technical people is impossible (nobody else uses it). And the plugin update firehose occasionally breaks things at 7 AM.
What are Obsidian’s limitations?
No real-time collaboration. If you need multiplayer docs, use Notion or Google Docs. Obsidian is a single-player tool that happens to sync.
Mobile is second-class. The mobile app works but the UX is clearly built for desktop-first. Voice notes, quick capture, fast search — all better in Apple Notes.
Plugin dependency risk. If you build your workflow on 10 community plugins and three get abandoned, you’re refactoring your vault on a Saturday. Stick to plugins with >1k stars and commits in the last 6 months.
No native AI. Out of the box, Obsidian is a markdown editor. The intelligence comes from plugins and external tools. Which is a feature — but it means the default experience is “fast Notion”, not “AI brain”. You have to build the brain yourself.
How much does Obsidian cost in 2026?
Obsidian is free for personal use — including commercial use if you’re a solo operator. Paid plans cover sync and publishing.
| Plan | Cost | What you get |
|---|---|---|
| Personal | Free | Full app, all features, local vault |
| Sync | $10/mo | End-to-end encrypted sync across devices |
| Publish | $20/mo | Host your vault (or parts) as a website |
| Commercial | $50/user/year | Required if company >2 people uses it for work |
I pay for Sync. Publish I skipped — I use Quartz (free) for public content. Commercial license kicks in at 2+ employees; solo operators are fine on personal.
Alternatives
| Tool | Best for | How it compares |
|---|---|---|
| Notion | Team docs, databases, client-facing wikis | Better collaboration, worse for linking. Cloud-locked. I left. |
| Logseq | Outliner-first, block-based notes | Free, open-source, MIT license. Similar philosophy, different UX. Less plugin firepower. |
| Roam Research | Networked thought, academic research | Pioneered bidirectional linking. Expensive ($15/mo), cloud-only, losing momentum. |
| Craft | Beautiful docs, Mac-first | Stunning UI, weaker linking, closed format. Great for presentations, not for brain. |
| Apple Notes | Quick capture, voice memos | Free, fast, zero structure. Use it for input → move the keepers to Obsidian. |
My take: if you want team collaboration, Notion still wins. For anything else — if you own your notes and take linking seriously — Obsidian is the answer. Logseq is the closest free alternative philosophically.
Bonus — One repo to make Obsidian a real brain
I’m not going to hand you a list. Most “AI for Obsidian” plugins are consumer productivity-hacker stuff — a chatbot UI stapled on top of your notes, lock-in dressed as convenience, a weekend project one maintainer away from abandonment. The plugin firehose is where people go to waste a Saturday.
The only repo worth starting from: heyitsnoah/claudesidian.
- 2.2k stars, pushed this week, MIT license
- A vault template structured PARA-style (Projects / Areas / Resources / Archive), built explicitly for Claude Code to read and write into
- Ships with kepano’s official Obsidian Skills baked in — Bases, Canvas, Markdown — so you’re not chasing outdated community plugins
- One command —
/init-bootstrapin Claude Code — and you’re running in ten minutes
Here’s the point. Your AI already works outside Obsidian: it’s called Claude Code, or Cursor, or whatever you use. You don’t need to install a chatbot plugin to talk to your notes. You need a vault structured well enough that an agent doesn’t get lost in it — and this repo gives you exactly that.
Everything else — in-vault copilots, embedding layers, MCP server sprawl — is scope creep dressed as a stack. Start here. Add nothing until it hurts.
The verdict
4 months. 3,400 files. Zero days I’ve wanted to go back to Notion.
Obsidian isn’t the best app in any single category. Notion collaborates better. Apple Notes captures faster. Craft looks prettier. But Obsidian is the only tool where my markdown, my AI agents, and my workflow all speak the same language — and the cost of switching is a folder move.
For a solo operator running AI on top of notes, the question isn’t “is Obsidian good enough?” It’s “what else even competes?”
Score: 9/10
The 1 point off: mobile UX is still rough, the plugin update firehose occasionally breaks things, and onboarding for a non-technical person is genuinely hard. But every morning, for 4 months, it’s been the first app I’ve opened. That’s the only review that matters.
Discover Obsidian at obsidian.md
Tool Friday is a weekly series where I review one tool I actually use in my workflow. Just tools that made my work better.