Here’s something embarrassing. I’m a systems engineer. Twenty-five years managing enterprise infrastructure. And until recently? My personal file system was a complete mess.
Files everywhere. iCloud, Dropbox, OneDrive, ProtonDrive. Two laptops. External drives with names like “Backup_OLD_FINAL_v2.” Folders buried 8 levels deep with names I made up in 2003 and haven’t thought about since.
At work, I help manage around 5,500 virtual desktops running on VMware ESXi. Before that, I spent years on the server side; I’ve probably built and retired over 15,000 virtual servers throughout my career. I can script my way through complex VMware migrations without breaking a sweat. But ask me to find that PDF of my home insurance policy? Yeah. Good luck with that.
If this sounds familiar, keep reading.
The Problem Nobody Talks About
Digital clutter sneaks up on you. It builds quietly, one “I’ll organize this later” at a time. Then suddenly you’re staring at a search bar, trying to remember which of four cloud services might have the document you need.
Productivity gurus love to say, “Just pick a system.” Easy for them. They’re usually not dealing with:
Work files that absolutely must stay separate from personal stuff
Sensitive documents that need encrypted storage
Collaborative projects scattered across different platforms
Years of accumulated digital life that doesn’t fit neatly anywhere
I tried everything. Color-coded folders. Strict naming conventions. Applied the “inbox zero” mindset to my files. Each approach worked for maybe three weeks. Then chaos won. It always does.
That’s when I stumbled onto Johnny Decimal, on Reddit, of course.
A System That Actually Made Sense
Johnny Decimal is a file organization method created by Johnny Noble. The idea is simple: you get a maximum of 10 areas (your broad categories), and each area can hold a maximum of 10 categories (more specific groupings). Every single file gets a unique ID based on where it belongs.
Instead of wading through /Documents/Work/Projects/2024/Client_ABC/Reports/Final/, you end up with something like 32.14 Client ABC Q3 Report.
The constraints are the whole point. When you limit yourself to 10 areas and 10 categories per area, you actually have to think about how you organize things. Nothing goes deeper than two levels. Every file has a home. You can tell someone “it’s in 32.14” and they know exactly where to look.
I read through Johnny’s documentation, and something just clicked. This wasn’t some organizational B.S. that would fade in six months. It’s a real framework for thinking about how information connects to other information.
But I had a problem.
The Gap Between Theory and My Reality
Johnny Decimal works great when you’re starting fresh with one file system. I was looking at four cloud services, two machines, and years of accumulated chaos that all needed to be cataloged, cross-referenced, and migrated.
I needed more than a methodology. I needed a tool.
Here’s what I was looking for:
A central index to track where everything lives across all my storage platforms
A way to assign and manage Johnny Decimal IDs without going crazy
Something that could grow with me as I slowly brought order to the mess
I searched for existing solutions. Some solid tools exist, but nothing quite fit my multi-platform, sprawling-digital-life situation.
So I built it myself. With an unusual partner helping me along the way.
Next time: What it actually looks like to build an app with AI as your collaborator—the process, the tool I created, and what I learned about this new kind of partnership.
Have you tried Johnny Decimal? Struggled with multi-cloud chaos? I’d love to hear your experiences in the comments.
Until next time—stay curious, keep scripting, and remember: every expert was once a beginner who just refused to quit. I’m James, and this has been As The Geek Learns.
One last thing: if you’re getting value from the show, drop me a rating on Apple Podcasts. Five stars keeps the lights on, but honestly? Even a review that says ‘this guy talks about PowerShell too much’ helps the algorithm. I’ll take it.
