Your second brain, with an AI chief of staff already hired.
Henry OS is a complete Obsidian vault system plus four Claude AI skills that run it for you. Open the vault, install the skills, and from day one Claude generates your daily brief, pressure-tests your decisions, and files away everything you learn. This is the system behind how I built Henry, my AI executive assistant.
What’s Inside
- The Henry OS Vault — a ready-to-open Obsidian vault: Inbox, Daily Briefs, Notes, People, War Room, Projects, plus battle-tested templates.
- 4 Claude Skills — Daily Brief, Council, Session Capture, and Vault Neatify.
- Install guide — 5-minute setup for Claude Desktop, claude.ai, or Claude Code. No plugins, no subscriptions, plain markdown.
Who It’s For
Anyone running their life or business out of Obsidian who wants an AI that actually operates the system instead of just chatting about it.
The Operating Rhythm
Morning brief, inbox to zero, decisions through the council, session capture at night. That loop is the whole system, and Claude runs it with you.
30-day money-back guarantee. Questions? Reply to your receipt email.
Pairs well with Anchor if you want a structured daily-weekly-monthly review system running on top of it, and with The Token Diet once your setup starts feeling heavy.
FAQ
Do I need to already use Obsidian?
Yes. Henry OS is a vault structure plus an AI layer that runs it, so it assumes you’re already on Obsidian.
Does this only work with Claude?
It’s built around Claude, but the vault and prompt structure are portable if you run a different AI assistant.