chief-of-staff

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.

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

Command	When	What It Does
/setup	Once	Conversational wizard. Generates CLAUDE.md, seeds .claude/memory/, copies vault templates.
/start	Opens every session	Reads Command Center + To-Do List. Delivers Must/Should/Could briefing. Flags overdue Waiting For items. Ends with "what do you want to work on?"
/sync	Mid-session (optional)	Checkpoint. Saves anything worth keeping to memory. Updates Command Center or To-Do if needed.
/wrap	Closes every session	Reflects wins. Updates Command Center date. Queues open threads. Rotates stale memory entries out.

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