file-organization

File Organization Guidelines

File Naming Rules

Core Conventions

• Title Case with spaces (not underscores or hyphens between words)
• Target under 60 characters for Finder/Explorer readability
• Filenames in English even if document content is in another language
• Consistent naming within folders — all tax receipts follow the same pattern, all passports follow the same pattern

Date Prefixes

• YYYY-MM-DD prefix ONLY when date is critical to the file's purpose or context
• Date based on original creation/event date (from file contents), NOT filesystem date
• If no date prefix, use word order: [Subject/Project] [Document Type] [Descriptor]
  • Example: "Fairbanks Summer Hours 2016"

Special Characters

• En dashes (–) for year ranges in folder names (e.g., "EastRise 2019–2025")
• Spaced en dashes for separating distinct elements (e.g., "Oliver Ames – Media Release")
• Common acronyms acceptable if universally understood (e.g., "POS", "HR", "Q1")

Versions

• Use: "v2", "Draft", "Final"
• Never use: "(2)", "(copy)", "Copy of", "New"

Examples

✅ Good:

2024-03-15 Board Meeting Notes.md
Lawson's Finest Interview Prep.docx
EastRise 2019–2025 Archive
Oliver Ames – Media Release.pdf
Q1 Marketing Report Final.pdf

❌ Bad:

board_meeting_notes_03-15-24.md
lawsons-finest-interview-prep (2).docx
01 EastRise Archive
media release copy.pdf
Q1 Marketing Report (Final Version).pdf

Folder Naming Rules

• Do NOT start with numbers (no "01 Archives", "02 Projects")
• Exception: YYYY-MM-DD prefixes are acceptable when chronology is the organizing principle
• Use clear, descriptive names that indicate contents

Examples

✅ Good:

Archives
Projects
2024-01 Tax Documents
EastRise 2019–2025

❌ Bad:

01 Archives
02 Projects
Tax Docs
Old Stuff

Organization Principles

Structure

• No loose files at root level of main folders — group into appropriate subfolders
• If multiple files of the same type exist, they belong in a folder together
• Match related files together (e.g., voice memo recordings with their transcripts in dated subfolders)
• Only move files to category folders if directly relevant

Photo Folders

• Large photo collections can be moved as parent folders without renaming individual files
• IMG_XXXX.jpeg files in personal photo folders don't need individual renaming
• Identify photo folders that should remain as-is

Voice Memos/Recordings

• Keep original audio files alongside their transcripts
• Organize into dated subfolders with matched recording + transcript pairs

Work Archives

• HR-related conversation records → "HR Documentation" folder
• Financial advisor correspondence → dedicated folders (e.g., "Trust Financial Advisement")
• Severance and separation documents → parent employment folder

Duplicate Detection

• Find EXACT duplicates only using MD5 checksums
• Verify duplicates by CONTENT, not just filename
• Move suggested duplicates to a review folder first
• Report the full path of each duplicate pair
• Keep the file with the better/clearer name; delete the cryptic one
• Files marked "safe to delete" in filename can be removed after verification
• Redownloadable statements (credit cards, banks) can be deleted if duplicates exist

The Process

When reorganizing files:

1. Deep analysis first — examine contents of every file
   • Use OCR/pdftotext for large PDFs that exceed API limits
   • Create temp smaller versions if needed, then delete temp files
2. Create a reorganization plan with proposed moves/renames
3. Get approval before execution
4. Execute carefully, verifying each operation
5. Verify work after changes
6. Track progress in case of context loss

Quick Reference

Element	Rule
Spaces	Yes, use spaces
Underscores	No
Case	Title Case
Date prefix	Only when date matters
Date format	YYYY-MM-DD
Year ranges	En dash (2019–2025)
Versions	v2, Draft, Final
Folder numbers	Never (no "01", "02")
Max length	~60 characters