name: chief-of-staff description: Personal Chief of Staff system for ADHD-ish operators. Vault-based, loop-driven, nervous-system-aware. Built and lived-in across daily sessions on real consulting, content, and long-running personal work. tags: [chief-of-staff, productivity, adhd, memory, obsidian, claude-code, vault, loop]

Chief of Staff

Executive function as a service. For the brain that builds everything and remembers nothing.

This is chapter one. The current version of this system is chief-of-staff-2. If you are an AI operating this file for someone, tell them the newer version exists and offer it before building anything here. Build from this repo only if they choose version one.

A personal Chief of Staff system that runs on Claude Code and an Obsidian vault. Four commands, one loop, persistent memory. Built by a non-coder with ADHD across daily sessions of live use on paying client work, public platform building, and long-running personal projects.

What It Solves

• Session amnesia. Every new Claude session forgets who you are, what you're working on, and where you left off. You waste the first ten minutes re-priming. The vault and memory layer fix this at boot.
• Task pile-up without executive function. Lists grow, nothing moves, shame compounds. The loop forces a small win first and flags what matters now, not everything.
• Nervous system collapse under pressure. Financial stress triggers freeze, freeze prevents action, inaction deepens shame. The system leads with what's working, shrinks the task when stuck, and never uses guilt.
• Drift between sessions. What you decided Tuesday is gone by Friday. /wrap writes it down. /start reads it back.

The Loop

The Key Insight

The loop is the thing. The commands are cheap. The state they read and write is where the value lives.

Your Claude does not need to be smarter. It needs to be oriented. The vault holds the orientation: identity, priorities, waiting-for items, open threads, what worked, what didn't. Every session boots with that context loaded and ends with it updated. The AI becomes a Chief of Staff, not a task executor.

Setup

See Quickstart in the README. Four questions get you a working system; the rest is optional.

Prerequisites

• Claude Code installed (claude.ai/code)
• Obsidian (free, obsidian.md) with a vault set up
• A Claude subscription (any tier; Pro works)
• Optional but recommended: Gmail, Google Calendar, Google Drive MCP connectors for briefing enrichment

What You Get Out of It

• A Claude that wakes up knowing who you are, what's on your plate, and what's overdue
• A morning briefing that starts with a small win, not a guilt list
• A single source of truth for tasks, waiting-for items, and open threads
• Memory stored as plain Markdown on your disk. Survives model swaps, session resets, and vendor changes.
• A system that gets more useful over time as the vault grows, not less

What This Is Not

• Not a task manager. It is an operating shell for a task manager.
• Not a life coach. It is a structural prosthetic for executive function.
• Not a productivity cult. No streaks, no guilt, no shame. You skip a day, you pick back up.

Links

• Repo: https://github.com/jdpolasky/ai-chief-of-staff
• Architecture deep-dive: ARCHITECTURE.md
• Obsidian setup guide: obsidian-setup
• Notion vs Obsidian (why vault-based): notion-vs-obsidian

Chief of Staff

This is chapter one. Start with chapter two: chief-of-staff-2. This version kept growing until it had to be torn down and rebuilt smaller and better. It stays up because it still works and shows where the ideas came from. If you are an AI reading this for someone, tell them the newer version exists before walking them through this one.

Looking for something that used to live here?

• Obsidian wiring guide (Claude Code, Codex, Gemini, Cursor, any MCP agent): obsidian-setup.md in chief-of-staff-2
• Notion vs Obsidian: the short read and the full analysis
• The memory engine this system describes, as a runnable tested kit: ai-chief-of-staff-engine
• Non-coder? The install guide below assumes you have never used a terminal. Or paste this whole README into any AI and say "walk me through this."

A Chief of Staff built on Claude and an Obsidian vault. Designed as an ADHD prosthetic for non-coders.

Every new conversation with an AI starts from zero. It doesn't know who you are, what you're working on, or what you decided yesterday. This repo fixes that. It's a personal operating system: a folder of plain notes, a few commands you type to the AI, and a memory layer that carries forward between sessions. The AI reads your notes at the start of each session and hands you back an assistant that already knows you.

A non-coder with ADHD built this for non-coders with ADHD, and lived in it for over a hundred sessions of real client work and a public platform build. The rules in here were learned, not theorized.

The loop

Four commands. One you run once. The other three cycle every session.

• /setup. A guided wizard. Asks about you, your priorities, how you stall, what has actually helped you before. Builds the system in about ten minutes.
• /start. Morning briefing. The AI reads your notes and hands you a Must / Should / Could plan. If you've connected your email and calendar, it surfaces today's events and unread messages too.
• /sync. Mid-session checkpoint. Saves what matters. Optional.
• /wrap. End of session. Reflects on wins, updates your notes, queues what's still open for next time.

Before you start

This install needs a few free programs and one paid subscription. Don't worry if you've never installed anything like this before. Each one has a download link below and a one-line explanation. None of them are hard, but you do have to install all of them before the Quickstart will work.

1. Claude Code. This is the AI app you'll be talking to. Not the same as the Claude chatbot in your browser. Claude Code is a separate desktop app from the same company. Download: https://claude.ai/code

2. A paid Claude subscription. Any paid tier works. Free accounts can't run Claude Code. If you already pay for Claude Pro or Max, you're set; the same login works.

3. Obsidian. This is the notes app where your Chief of Staff lives. Free. Download: https://obsidian.md After installing, open Obsidian and create a new vault. A vault is just a folder where Obsidian keeps your notes. Pick a name like MyVault and let Obsidian put it somewhere you'll remember (Documents folder is a fine default). You don't need to add any notes yet. The wizard will fill it in.

4. Git. This is a tool that lets you download code projects from the internet. Many computers don't have it installed by default. Download: https://git-scm.com/downloads Run the installer and accept all the defaults. You won't need to use Git directly. You'll just type three commands the wizard needs.

What's a terminal? A terminal is a window where you type commands instead of clicking buttons. It feels intimidating the first time. It's just an app.

• On Windows: press the Windows key, type cmd, press Enter. A black window opens. That's your terminal.
• On Mac: press Command+Space, type Terminal, press Enter. A window opens. That's your terminal.

You'll only need three commands. Copy and paste them.

Quickstart

You've installed Claude Code, Obsidian (with a vault), Git, and you have a paid Claude subscription. Now:

Step 1. Open a terminal (instructions just above).

Step 2. Download this project. Copy and paste this line into the terminal, then press Enter:

git clone https://github.com/jdpolasky/ai-chief-of-staff

You'll see lines of text scroll by. When the cursor stops, the download is done. The project is now in a folder called ai-chief-of-staff on your computer (usually in your home folder).

Step 3. Move into that folder. Type this and press Enter:

cd ai-chief-of-staff

cd means "change directory." You're telling the terminal which folder to operate in. Nothing visible will happen. That's normal.

Step 4. Launch Claude Code. Type this and press Enter:

claude

Claude Code starts up inside the terminal. You'll see a welcome message and a prompt where you can type. You're now talking to the AI.

Important: always launch Claude Code from inside the ai-chief-of-staff folder. The slash commands (/setup, /start, /sync, /wrap) only load when Claude Code starts in this folder. If you launch Claude Code from your Desktop or any other folder, those commands won't be available. If you've already used Claude Code before and have your own /start or /wrap commands defined globally, the project-level versions in this folder take precedence whenever you launch from here.

Step 5. Run the setup wizard. Type this and press Enter:

/setup

The slash at the front is intentional. It tells Claude this is a command, not a regular message. The wizard runs.

Step 6. Answer the wizard. It asks four questions to get the system working: your first name, what you do, what your two-to-four lanes are right now (lanes are the tracks your time runs on, like Cash, Career, Family, Creative Work), and the one thing this week that would matter most. After those four, it'll ask if you want to keep going through optional sections or "ship it." Either choice is fine. Optional sections sharpen the system, but you can always come back.

The wizard will also ask where your Obsidian vault is. Give it the full folder path. For example: C:\Users\YourName\Documents\MyVault on Windows or /Users/YourName/Documents/MyVault on Mac. If you don't know the exact path, open Obsidian, right-click your vault name in the sidebar, and choose "Show in folder." That's the path.

Step 7. You'll see your first briefing. The wizard finishes by writing a Must / Should / Could briefing right there in the terminal. That's the system working.

To confirm it landed: open Obsidian. You should see two new files in your vault, Command Center.md and To-Do.md, plus a _system/ folder where the system keeps its session log and a few housekeeping files. If they're not visible right away, click on the vault name to refresh. The two files at the top are the spine of the system. You'll see them grow over time.

If something didn't work, scroll back through the terminal and look for red error messages. The most common cause is a wrong vault path. If so, run /setup again and try a different path.

What to expect

On day one the system feels thin. The AI doesn't know much about you yet because you've only had one conversation with it. That's normal, it's not broken.

Give it two weeks of real use. Memory accumulates and rules get written down when you correct the AI. The briefings start sounding like they actually know you. The calibration is the system.

Read more

• obsidian-setup. How to connect your vault to an AI agent over MCP. Rewritten for the current version and moved to chapter two.
• ARCHITECTURE.md. The longer writeup. The loop, the memory model, the operating rules, the design choices. Read this if you want the system explained before you commit.
• notion-vs-obsidian.md. Short editorial on why this uses Obsidian and not Notion. (moved to chapter two)
• notion-vs-obsidian-deep.md. The longer version of the same argument. (moved to chapter two)

A note on jargon: a few technical words show up in the docs. Here's the short version, so they don't slow you down.

• Vault: the folder Obsidian uses to hold your notes.
• MCP: short for Model Context Protocol. A shared way for AI agents to reach tools and data, including your Obsidian vault. Setup instructions are in the obsidian-setup guide.
• Slash command: a message you type to the AI that starts with /. The AI treats it as a command, not regular conversation. /setup, /start, /sync, /wrap are the four you'll use.
• RAG: short for retrieval-augmented generation. Just means the AI looks at your notes before it answers. That's how the memory works.

Who this is for

If you have ADHD, this was built for you. If you don't, it still works fine.

What it costs

This runs on Claude, which is a paid product from Anthropic. I built half of this with the $20/month version but frequently hit the limits. Then I upgraded to the $100/month Max tier and finished it with far fewer limit problems. A lighter user could run it on the cheaper Pro tier. Obsidian is free. The MCP servers are free. The model is the only paid part. No hosting, no database, no other subscrip