Obsidian, Claude Cowork, Gmail, ClickUp, TextExpander
Nick Milo · Jun 5, 2026
TL;DR
What did Nick Milo use Obsidian for?
A note-taking educator with about 17,000 Obsidian notes gave Claude Cowork three map files (me.md, a vault map and a skill map) so it can find the right notes, and a scheduled skill writes a daily brief every morning. They say the brief is already waiting on their phone by the time they're in the kitchen.
What they did
They keep AI files in a separate AIOS folder inside the vault. A me.md file says who they are and how to work with them, and the CLAUDE.md file only says to read me.md so they can switch AI tools later. A vault map tells the AI where things live, and a skill map lists the skills (stored in their own notes, not inside Claude) and when to use them. Each session opens with a TextExpander snippet asking Claude to read me.md, review the maps and wait. A recurring daily brief skill runs at 6 a.m., pulling from Gmail, the calendar, ClickUp and the vault: weather, yesterday's progress, open loops, deadlines, book progress and the two or three things to do today. They leave replies inside the brief in curly brackets for the AI to act on.
How it went
They say the brief is already waiting on their phone by the time they're in the kitchen.
Worth knowing
- Pointing an AI at a large vault without maps leads it to sample a few notes and pretend it read everything. They use Sonnet for most work, Opus for heavy synthesis, and Haiku only for simple clipping summaries. Files sit on Anthropic's servers for a rolling 30-day window.
- Price check: Obsidian: free plan; Sync: US$5/month, or US$4/month on a yearly plan (US$48/year) (checked Oct 26, 2026); Claude: free plan; Pro: US$20/month, or US$17/month on a yearly plan (US$200/year) (checked Nov 1, 2026); ClickUp: free plan; Unlimited: US$10/month, or US$7/month on a yearly plan (US$84/year) (checked Oct 26, 2026).
Paying for Claude? See cheaper Claude alternatives.
Try it yourself
Paste this into a chatbot, then add your own details underneath.
First, read my me.md file in the Ideaverse folder. Then review the vault map and skill map for relevant context. Confirm you've read them, then wait for my instruction.
Original post
See Nick Milo's original post on YouTube → (Jun 5, 2026)
Sources
- Nick Milo on YouTube, Jun 5, 2026 — the original post
- Obsidian pricing — checked Oct 26, 2026
- Claude pricing — checked Nov 1, 2026
- ClickUp pricing — checked Oct 26, 2026
