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
bash
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 (, )
- 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 (, , , ) with WIP/FINAL_APPROVED separation
- Finance/personal docs: include expiry dates in filenames (), 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:
bash
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: for correct alphabetical sort
- Formula:
[Date]_[Context]_[Description]_[Version].ext
- Zero-padded versions: , (minor: )
- Separators: or (never spaces)
- All lowercase, filenames under 25-30 chars, let folder context provide the rest
- Zero-pad sequences: , (prevents sort)
- Status prefixes when useful: , , ,
- Avoid: , accents, emoji, leading dots, Windows reserved names (, , , )
- 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 |