File Organizer

Instructions

1. Understand Scope

Ask clarifying questions before starting:

• Which directory needs organization?
• Main problem? (can't find things, duplicates, no structure, general mess)
• Files or folders to avoid? (active projects, sensitive data)
• How aggressive? (conservative vs comprehensive cleanup)

For broad reorganization, briefly propose a philosophy from the reference guide (PARA, Johnny Decimal, GTD, 7-Folder). Let user choose - never force one. Skip for scoped tasks like cleaning Downloads.

2. Analyze Current State

ls -la [target_directory]
find [target_directory] -type f -exec file {} \; | head -20
du -sh [target_directory]/* | sort -rh | head -20
find [target_directory] -type f | sed 's/.*\.//' | sort | uniq -c | sort -rn

Summarize: total files/folders, type breakdown, size distribution, date ranges, obvious issues.

Anti-patterns to flag:

• Desktop used as permanent archive (goal: zero permanent files on Desktop)
• Unnamed folders (New Folder, New Folder (3))
• Broken versioning (document_FINAL_v2_DEFINITIVE_copy.docx)
• Downloads folder never cleaned (thousands of unsorted files)
• Same file duplicated across locations (use shortcuts instead)

3. Identify Organization Patterns

By type:

• Documents (PDF, DOCX, TXT), Images (JPG, PNG, SVG), Videos (MP4, MOV)
• Archives (ZIP, TAR, DMG), Code/Projects, Spreadsheets (XLSX, CSV), Presentations (PPTX, KEY)

By purpose:

• Work vs Personal, Active vs Archive, Project-specific, Reference, Temporary/scratch

By date:

• Current year/month, Previous years, Very old (archive candidates)

Context-specific structures:

• Photos/Video: Year/YYYY-MM_event-location/ with RAW, Edited, Export subfolders
• Music: Artist/[Year] Album/NN - Track.ext
• Work projects: numbered prefixes (01_Brief/, 02_Research/, 03_Assets/, 04_Deliverables/) with WIP/FINAL_APPROVED separation
• Finance/personal docs: include expiry dates in filenames (passport_exp_2030.pdf), organize by year then type
• Code: map local paths to remote URLs (github.com/username/repo/)

See references/organization-guide.md for detailed templates.

4. Find Duplicates

When requested:

find [directory] -type f -exec md5 {} \; | sort | uniq -d
find [directory] -type f -printf '%f\n' | sort | uniq -d

For each duplicate set: show paths, sizes, dates, recommend which to keep. ALWAYS confirm before deleting. Suggest shortcuts/aliases instead of keeping copies.

5. Propose Organization Plan

Present plan before making changes. Include:

• Current state summary (file count, size, type breakdown, problems found)
• Anti-patterns detected
• Proposed folder tree structure
• Changes to make: new folders, file moves, renames, deletions
• Files needing user decision (ambiguous placement)
• Ask for explicit approval before proceeding

6. Execute Organization

After approval, organize systematically.

Rules:

• Always confirm before deleting anything
• Log all moves for potential undo
• Preserve original modification dates
• Handle filename conflicts gracefully
• Stop and ask on unexpected situations

File renaming conventions (only when user agrees - never auto-rename):

• ISO dates: YYYY-MM-DD for correct alphabetical sort
• Formula: [Date]_[Context]_[Description]_[Version].ext
• Zero-padded versions: v01, v02 (minor: v01.1)
• Separators: kebab-case or snake_case (never spaces)
• All lowercase, filenames under 25-30 chars, let folder context provide the rest
• Zero-pad sequences: 001, 002 (prevents 1, 10, 11, 2 sort)
• Status prefixes when useful: WIP_, DRAFT_, REVIEW_, APPROVED_
• Avoid: < > : " / \ | ? *, accents, emoji, leading dots, Windows reserved names (CON, PRN, AUX, NUL)
• Watch full path length approaching Windows 260-character limit

7. Provide Summary

After organizing, report:

• Folders created, files organized, space freed, anti-patterns fixed
• New folder tree structure
• Maintenance schedule (below)
• Custom bash commands for ongoing cleanup

Maintenance Schedule:

Frequency	Time	Tasks
Weekly	15 min	Empty Downloads, process Inbox to zero, verify recent files are in place
Monthly	45 min	Scan for duplicates, verify backups, archive completed projects
Quarterly	2 hrs	Disk space audit, archive projects inactive 3+ months, test backup restore
Yearly	Half day	Disaster recovery test, retention policy review, structure update