cleanup

name	cleanup
description	Clean and organize Desktop files and conversations/ folder. Deletes stale research, empties trash, moves misplaced files to proper domains. Use when user says "clean up desktop", "organize files", "declutter", or when Desktop/conversations/ gets cluttered.

Desktop Cleanup

Aggressive but safe cleanup of Desktop root and conversations/ folder.

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Protected (Never Delete)

Always Keep

• IDENTITY.md, MEMORY.md, TODAY.md, SYSTEM-INDEX.md
• morning-brief.md (daily output)
• Domain folders: career/, finance/, health/, learning/, and any domain folders you've set up
• App folders: email-triage/, any with APP-SPEC.md
• System folders: logs/, projects/, diagrams/

In conversations/

• Active specialist folders — Check team("list") before deleting any session-id folders
• Chief's folder — Keep clean but don't delete (contains handoffs and temp files)
• Files < 24 hours old — May be in active use

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Cleanup Actions

1. Audit Desktop Root

List all files and folders:

ls -la Desktop/

Move misplaced files:

• PDFs about learning → learning/
• Resume/portfolio files → career/
• Specs (ending in -spec.md) should stay on Desktop root (correct location)

Delete stale research:

• Old .md files (> 3 days, not specs, not in a domain folder)
• Temporary outputs no longer needed (NOT specs - those persist)

Ask before deleting:

• Anything unclear in purpose
• Folders that might contain active work

2. Clean conversations/

ls -la Desktop/conversations/

Check for active specialists first:

team("list")

Safe to delete:

• Specialist folders NOT in active list (> 3 days old)
• Temporary files in chief/ (after organizing to Desktop or deleting)
• .py, .txt, .json temp files

Keep:

• Any folder matching an active specialist ID
• chief/ folder itself (but clean its contents)
• handoff-*.md files (auto-generated, needed for reset)
• Files modified in last 24 hours

3. Empty Trash

rm -rf Desktop/.trash/*

Always safe — trash is for deleted items.

4. Check _paused/

If exists, audit contents. Usually safe to delete if folders are empty or contain only stale placeholders.

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Cleanup Conversation Flow

1. Show current state:

   Desktop: X items (Y folders, Z loose files)
   working/: X items (Y specialist folders, Z files)
   .trash/: X items
   

2. Propose actions:

   • "Delete these stale specialist folders: [list]"
   • "Move these to proper folders: [list]"
   • "Clean chief/ folder: [list of temp files to organize/delete]"
   • "Keep these (active/recent/specs): [list]"

3. Get confirmation for anything ambiguous

4. Execute and report:

   Deleted: X items
   Moved: Y items
   Kept: Z items
   

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Example Session

User: clean up my desktop

Claude: Let me audit Desktop and working/.

**Desktop/** (25 items)
- 4 core files ✓
- 8 domain folders ✓
- 6 stale research files (> 3 days)
- 2 misplaced files
- 5 other folders to check

**working/** (45 items)
- 2 active specialists (keep)
- 12 old specialist folders (delete)
- 28 stale .md files (delete)
- 3 spec files (keep)

**Proposed:**
- Delete 6 stale Desktop files
- Move resume.docx → career/
- Move system-design.pdf → learning/
- Delete 40 items from working/
- Empty .trash/ (15 items)

Proceed?

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Anti-Patterns

Don't	Why
Delete without checking team("list")	May kill active specialist work
Delete -spec.md files	These drive specialist loops
Delete files < 24 hours old	May be in active use
Delete domain folders	These are permanent structure
Delete without showing what	User should see what's being removed

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Success Criteria

• ✅ No active specialist work disrupted
• ✅ No spec files deleted
• ✅ Misplaced files moved to correct domains
• ✅ Stale research cleaned
• ✅ working/ reduced to active items only
• ✅ .trash/ emptied
• ✅ User informed of all changes