File Management

File Management System

A practical framework for organizing digital files — born from studying two distinct approaches: a creator's asset-heavy workflow (Ami) and a knowledge worker's information architecture (Jeffrey). The core insight: organize by where you'll use it, not where you found it (David Allen).

Guiding Principles

1. Function over form. A folder structure that looks beautiful but requires discipline you don't have is worse than a slightly messy one you actually maintain. The best system is the one you stick to.

2. Organize by usage context. Meeting notes for Project A go inside Project A's folder — not in a global "Meeting Notes" folder. When you open the project, everything is there. When you share it, everything goes with it.

3. Name for searchability. The goal is: 6 months from now, you can find this file in under 30 seconds. That means consistent naming conventions, not perfect ones.

4. Don't over-optimize. Five levels of nested folders with a rigid numbering taxonomy will be abandoned in two weeks. Start simple, add structure only where friction actually appears.

5. Dual backup, always. Cloud + local. Never a single point of failure for anything you can't afford to lose.

Folder Structure

The Numbered Framework

Borrowed from Johnny Decimal, simplified. Use two-digit prefixes to control sort order and signal priority:

Root/
  01-Active/          # What you're working on right now
  02-Work/            # Work-related (projects, clients, deliverables)
  03-Personal/        # Personal documents, finances, health
  04-Reference/       # Things you look up regularly (templates, IDs, guides)
  05-QuickShare/      # Temporary staging area for files to share with others
  06-Assets/          # Reusable resources (fonts, icons, music, graphics)
  07-Archive/         # Completed projects, cold storage staging
  99-Archive/         # Deep archive — stuff you can't delete but rarely touch

Not every folder is required. Use only the categories your life actually needs. The key rules:

• Lower number = used more often. If you access Personal files daily but Work files weekly, swap 02 and 03.
• 99 is always archive. It's the "I can't delete this but I never look at it" bin.
• Max 5 levels deep. Beyond that, you'll get lost. The 6th level must be files only.
• Max 99 folders per level. You'll rarely need more than 10.

Per-Project Structure

For active projects (especially creative/media work), use this template inside the project folder:

ProjectName/
  01-Source/           # Raw footage, original files, source data
    Camera-A/
    Camera-B/
    Screen-Recordings/
  02-Working/          # Work-in-progress, drafts, iterations
  03-Output/           # Final deliverables (video, PDF, slides)
  04-Assets/           # Project-specific reusable elements
  README.md            # Brief project description, dates, status

This mirrors Ami's creator workflow: separate raw inputs from finished outputs so you can archive source material independently of deliverables.

Photo Management

For personal photo libraries:

1. Cull with reverse selection. Instead of marking favorites, delete everything first (move to trash), then recover the keepers from trash. Psychologically faster than heart-ing photos one by one.

2. Album naming: YYYY-MM Event

   • 2025-03 Japan Trip
   • 2024-12 Mom Birthday

3. Archive cycle. Every 2-3 years, move older photos from phone/cloud to external drive. Keep the last 2 years on-device for quick access.

4. Dual storage. Cloud library (iCloud/Google Photos) for sync across devices + periodic backup to external drive.

Naming Conventions

Date-Based Naming

Choose granularity based on how you'll search for it:

Rule of thumb: the more granular the date, the more you need to know which parent folder it lives in. Use full dates only when the parent folder provides context (e.g., Jeff's Sharings/2025-05-05-Inbox-Zero-Training.docx).

Type Keywords

Prefix or suffix files with a consistent type keyword. Pick 5-8 and stick to them:

doc-       # Documents, reports
notes-     # Meeting notes, personal notes
wk-        # Working/draft files
brief-     # Briefs, briefings
slides-    # Presentations
form-      # Forms, templates
ref-       # Reference material

Combined: 2025-Q1 doc-Quarterly-Business-Review

90% findability rule: if you combine a project name + one type keyword, you should find the file in search. That's the bar.

Folder and File Naming Rules

• Use hyphens or underscores, never spaces (shell-friendly, URL-friendly)
• No special characters except - and _
• Lowercase or Title-Case consistently — pick one
• Keep names under 60 characters when possible
• Lead with what changes most (date) so sort order is useful

Storage Strategy

Three-Tier Architecture

Cloud Sync Tips

• Pin frequently used folders offline. In iCloud Drive, right-click > "Keep Downloaded" for folders you open daily. Avoids the spinner tax.
• Use color labels / custom icons on important folders. In macOS: right-click folder > Get Info > drag image onto the icon. Especially useful for external drives.
• Quick Share folder (05) is a staging area: copy slides/docs here before sharing, so the original stays in its organized location and you don't create duplicates.

Backup Rule

3-2-1: 3 copies, 2 different media types, 1 offsite.

Practical version for most people:

1. Working copy on laptop
2. Cloud sync (iCloud / Google Drive / Dropbox)
3. Periodic backup to external drive

Shared Files and Collaboration

When someone shares a file with you, decide immediately:

For shortcuts: create a pointer in your own folder structure (e.g., inside 02-Work/ProjectX/) that links to the original. You organize your way, the owner organizes theirs.

Starred / Flagged files: maximum 5 at any time. If everything is starred, nothing is. Criteria for starring:

1. Used every single day
2. Need quick access on phone too
3. Can't be easily searched for

Metadata Tricks

For files you can't rename (shared docs, system files):

• Google Drive: Press D > Details > add keywords in the Description field. Now searchable by those keywords.
• macOS Finder: Cmd+I > add keywords in Comments field. Searchable via Spotlight, Alfred, or Raycast.
• Windows: Right-click > Properties > Details > add Tags.

Audit Checklist

When helping a user clean up their files, run through this:

1. Inventory. What's in the root? What's taking up space?
2. Frequency. What do they actually open daily vs. never?
3. Pain points. Where do they waste time looking for things?
4. Current habits. What naming conventions do they already use (even informal ones)?
5. Constraints. Cloud storage limits? External drives? Team sharing requirements?

Then propose a structure that starts from their current state — don't prescribe a perfect system they'll never adopt. Migration should be gradual:

• Week 1: Set up top-level folders, move the obvious stuff
• Week 2: Rename the 20 most-accessed files with consistent convention
• Month 1: Archive completed projects
• Ongoing: Apply the system to new files as they're created

Quick Reference: Search Operators

Anti-Patterns

Things that look organized but create friction:

• Global "Meeting Notes" folder. Scatters context. Keep notes with their project.
• Color-coding everything. Reserve colors for 2-3 critical categories max.
• Too many subcategories upfront. You're planning for a library you don't have yet. Add folders when you have 5+ files that belong together.
• Renaming shared files. Breaks the owner's ability to find them. Use keywords/metadata instead.
• Keeping everything "just in case." That's what 99-Archive is for — but set a yearly purge reminder.