Most people deal with messy folders by promising to clean them up “later.” This approach gives that job to an AI with a written rulebook, and it keeps working every day. I just watched a breakdown from productivity creator Jeff Su, and he’s had this system renaming and filing his documents automatically for five months.
There’s a catch, and he says so up front. You need about 15 minutes to write a rulebook that teaches the AI how you like things organized. After that, the AI does the boring part. I like that it isn’t tied to one tool. It works with ChatGPT, Claude and Gemini, and with Google Drive, Dropbox, OneDrive and iCloud Drive.
The key idea: write a rulebook, not a to-do list
The author’s main point hit home for me. We already know we should organize our files. We just don’t want to do the dull renaming and moving every time a new PDF shows up.
His example is spot on. Your doctor emails a health report. You download it, and it sits in your Downloads folder with some random name. You know it should be called something like “Annual Health Report” and live under Health > Resources > Annual Health Reports. But that’s effort, so it stays in Downloads.
The fix is a plain text rulebook the AI can read and update. It has three parts:
- An organization framework: where each file goes and why. The creator uses an “area-first” version of Tiago Forte’s PARA method (Projects, Areas, Resources, Archive). You start with a part of your life or work, like “Health” or “Product Marketing.” Inside each one you add Resources (things you keep going back to), Projects (active work that has an end date) and Archive (finished or old material).
- Naming conventions: rules that keep names consistent and easy to search. Standalone documents get short, clear names like “Email Subject Line Best Practices.” Project folders start with the year and quarter, so you know when they began. Receipts and invoices include the full date, so you can pick out one specific record.
- A filing workflow: tells the AI when to stop and ask you, and how to save your answers so it doesn’t ask the same thing twice.
Old way vs. new way
Here’s the difference as I see it.
The old way: You’re the filing clerk. Every file means a decision about its name and where it goes. You’re busy, so you skip it, and things pile up in Downloads or a vague parent folder. Finding them later turns into a search party.
The new way: You’re the reviewer. Files go into one inbox folder. The AI reads each one, suggests a new name and a location, and waits for your okay. Most days you just type “approved.”
The clever bit is that the system learns. In the demo, the AI couldn’t tell whether two receipts were personal or business purchases. So it asked. The author told it which card was which by the last digits and asked it to remember that. The AI then added a “card rule” to the rulebook on its own. The next batch of receipts got filed without any questions.
The expert says you’ll give more feedback in the first few days, while the AI hits new cases. After about two weeks, he says, the daily reports are around 95% accurate and need very little input from you.
One warning he’s clear about: this won’t work in a normal web chat. You need the desktop apps (ChatGPT, Claude or Gemini) because the AI needs direct access to files on your computer.
🛠️ How to set it up
Step 1: Start with a test folder.
Create a root folder with subfolders like “00 Inbox,” “01 Reference,” “Personal Finances,” “Business Finances,” “Health” and “Travel.” Download the creator’s starter rulebook as a Markdown file and put it in “01 Reference.”
Step 2: Give the AI access and run a first pass.
Connect the desktop AI app to your root folder. Drop a few real files into the inbox and prompt: “Read my rulebook in the 01 reference folder and help me organize the files in the inbox folder.” The AI shows a summary first, then each file’s current name, suggested name and suggested location. Nothing moves until you approve.
Step 3: Map your existing cloud storage.
This is where it gets really interesting. Install the desktop app for Google Drive (or Dropbox, OneDrive or iCloud) so your cloud folders show up in Finder or File Explorer. Then ask the AI for two snapshots:
- 📂 Current state: how your files are organized right now, shown as a folder tree
- 🗺️ Future state: how they could be organized under your rulebook
In the author’s demo, the AI mapped his whole drive and flagged real problems, like business finance records sitting in two places. It also asked clarifying questions. Answer them, because that’s how it learns your preferences.
Step 4: Move things yourself the first time.
This surprised me. The expert suggests doing the first reorganization by hand, with the AI telling you what to move and where, step by step. That way you actually learn where everything lives. Start with the areas you use most. Move whole folders where you can, and skip renaming for now so it doesn’t become a giant project.
Helpful tips from the video:
- You don’t need to make your whole drive available offline. The AI can read folder and file names without it.
- Want a clean start? Make a “Legacy” folder at the root, dump everything unsorted into it, and bring files back over time.
- It’s fine to break your own rules. He keeps a “Quick Share” folder at the root for convenience and writes it into the rulebook as an exception.
- Ask the AI to look at a messy folder and suggest subfolders. Claude grouped his business records into four new subfolders this way.
Step 5: Automate it with a daily task.
Create a “00 Inbox” folder at the root of your drive and pin it to Favorites (Mac) or Quick Access (Windows). Test a few files and give feedback until the results look right. Then, in the same chat, ask the AI in plain English to create a daily scheduled task that checks the inbox and suggests changes for you to approve. Make sure the task runs in the project folder that holds your rulebook and can access your drive.
⚡ Why I think this works
The AI isn’t guessing. The rulebook sets the principles, and your folder structure plus saved preferences show it how to apply them. Each time you correct it, the system gets a bit better. The creator also uses the same idea at work, with an AI setup that renames and sorts video footage into Dropbox for his editor.
The full video walks through every screen, including the exact prompts and the free starter rulebook. It’s worth watching if your Downloads folder is starting to look like a junk drawer.