Stop Organizing Files Yourself.

Video authored by the channel shown, not by IANIA; all rights belong to the creator. Transcript and summary generated automatically; the original-language content is preserved.

Original language: English

Original video: Stop Organizing Files Yourself. · Channel: Jeff Su · 14:29 · Watch on YouTube

Topics: AI agents, Task and workflow automation, AI models

Summary

The video presents a rulebook-based system for having AI rename and file incoming documents according to your preferences. The rulebook sets out an organization framework, naming conventions, and instructions for when the AI should ask questions and save new preferences. The creator demonstrates the approach with local folders, Dropbox, and Google Drive, recommending that users review proposed changes and guide the initial organization. Once preferences are established, a scheduled task can review an inbox, propose changes for approval, and update the rulebook with new instructions.

Key points

Create a rulebook explaining where files belong, how they should be named, and when the AI should ask for clarification.
The creator adapts the PARA framework by organizing around life or work areas, with resources, projects, and archive subfolders.
Choose naming patterns based on what you will need to find later, such as descriptive titles, project dates, or full dates for transactions.
Give the AI access to the rulebook and an inbox folder, then review its proposed names and destinations before approving changes.
When you clarify an unfamiliar case, ask the AI to save that preference in the rulebook for future use.
For an existing cloud drive, first map its current structure and compare it with a proposed structure based on the rulebook.
The creator recommends guiding the first reorganization yourself, moving frequently used areas first, and postponing renaming.
A scheduled task can check the inbox daily and present proposed changes for review and approval.

Chapters

Start	Chapter	Summary
00:00	Why use AI to organize files?	The creator introduces an AI filing workflow and explains the need for a rulebook covering organization, naming, and clarification.
03:41	Build the rulebook and organize an inbox	The creator sets up folders and a rulebook, then demonstrates how AI proposes and applies file names and locations while learning a receipt preference.
07:47	Apply the system to cloud storage	The video shows how desktop cloud-storage folders can be made available to AI, which maps the current drive and proposes a future structure.
11:24	Reorganize existing files	The creator recommends answering the AI’s questions and using it to guide a gradual, hands-on move into the proposed folder structure.
12:26	Set up a scheduled inbox workflow	The creator explains how to test the rulebook on inbox files and ask the AI to run a daily task that proposes changes for approval.

Quotes

three essential things you need to include in your rulebook. — 01:35

remember the card rule. — 05:14

First, the current state showing how my files are organized right now. — 09:21

Start with area folders you use frequently and move existing folders together where possible. — 11:24

You drop the files you want to keep into your inbox folder — 13:58

Concepts and entities

rulebook, PARA framework, Area-first PARA framework, ChatGPT, Claude, Codex, Gemini, Dropbox, Google Drive, Tiago Forte, Jeff Su

Full transcript (original language)

00:00 This is my inbox folder, and throughout the day, it fills up with files I want to keep: reports, spreadsheets, screenshots, receipts, et cetera. But instead of organizing all of this myself, my AI automatically reads each file, gives it a descriptive name, and moves it to the right folder. It’s been doing this every day without fail for the past 5 months. Now, if you think that sounds too good to be true, there is a catch. You need to spend around 15 minutes up front creating a rulebook to teach your AI how to organize files according to your preferences. And the

00:32 best part? The framework I’m about to share works across all the major AI tools like ChatGPT, Claude, Gemini, and across all the major storage platforms. [music] So this setup’s going to work no matter what tool you use. Let’s get started. Diving right into a situation we’ve all found ourselves in. Say your doctor sends you your latest health report over email. After clicking download, the PDF lands in your downloads folder. At this moment, [music] you know you should give it a useful name like 2035 annual health report. And you know you should organize it under your health folder, resources,

01:04 annual health reports, so that you can find it easily next time. But that’s a lot of work. So maybe you just throw it under the health parent folder, telling yourself you’ll do it later, right? Or you just leave it in downloads. So the problem isn’t that we don’t know we should organize our files. We all have a rough idea in our heads of how we want to do it. The problem is having to do that tedious work every time a new file comes in. So wouldn’t it be great if we can just set the rules and have AI do the grunt work of renaming and filing for us? On that note, let’s cover the

01:35 three essential things you need to include in your rulebook. First, an organization framework that tells the AI where a file belongs and why it belongs there. Second, naming conventions so the AI keeps the file names consistent and easy for you to find later. And third, a filing workflow that tells the AI when to ask for clarification. Starting with the organization framework. Longtime viewers know I’m a huge fan of Tiago Forte’s PARA framework that organizes your files by projects, areas, resources, and archive. I won’t waste your time nerding out about that today,

02:06 so I’ll link to Tiago’s video below. My version is the area-first PARA framework, which I think fits more naturally with how we look for files. You basically start with an ongoing part of your life or work. For example, health. And within the health area folder, we have a resources subfolder that holds material referring to, like folder of annual health reports or a standalone insurance claim template for reimbursements. We also have a project subfolder that holds active work with a clear end point, like researching and planning for LASIK eye surgery. And an

02:37 archive subfolder that holds completed projects or outdated records I want to keep, like health insurance coverage from previous years. It’s the exact same idea for work-related areas. For example, in this product marketing area folder, product marketing resources might contain a brand kit holding my logo and brand guidelines. The projects [music] folder contains projects I’m actively working on, and the archive folder holds completed or inactive material. Moving on, naming conventions make files easier to find. So, as a rule

03:09 of thumb, use a consistent pattern based on the details you look for later. For example, if I have a standalone document, I keep the name short and descriptive, like email subject line best practices, so I know what’s inside without opening it. For project folders, I put the year and quarter first, like 30 Q3 trip to Seattle, so I know when the project started and what it’s about. And for records of a specific event or transaction, like receipts and invoices, I include the full date, as in Help Scout invoice 2030 0609, right? So I can

03:41 identify the particular record I need. Finally, the filing workflow basically tells the AI what to do when it runs into something the rulebook doesn’t cover, and how to save our preferences so it knows what to do next time. On that note, let’s jump into a real example. First, create an empty folder somewhere on your computer. I’ll call mine JS root folder, and inside [music] it create 00 inbox, 01 reference, personal finances, business finances, health, [music] and travel. Next, open the starter file management rulebook

04:11 I’ve linked below. Go to file, download, markdown.md, and move that file into 01 reference. And this gives us a plain text rulebook that AI can read and update. Then, give your AI access to the root folder you created earlier, and I’ll name my project file management. And although I’m using ChatGPT work in this example, you can use the same rulebook approach in Claude, Codex, and Gemini Spark. And just to be clear, this will not work in a normal web chat. You need to use the desktop versions of ChatGPT, Claude, and

04:42 Gemini since they need direct access to the files on your computer. Now, I’ll move these four files I know I want to keep from downloads into the inbox folder. Then, back in ChatGPT work, I’ll say, “Read my rulebook in the 01 reference folder and help me organize the files in the inbox folder.” And [music] we’re just going to fast forward a little bit here. First, the AI gives us the bottom line up front, followed by a breakdown of its proposed changes. Each file’s original name, proposed new name, and proposed location. For example, it picked travel for the itinerary and health for the visit

05:14 transcript. And nothing has been moved yet. But check this out. The AI is asking me to clarify whether these two purchases are personal or business because it [music] can’t tell from the receipts alone. And so I reply, “My personal credit card ends in 8888 and my business card ends in 9090. Go ahead with all four files and remember the card rule.” And we’ll fast forward again. And just like that, all four files are renamed and moved to their respective folders. And now if I open the rulebook and look under the organization framework section, you can see the AI saved our card rule so it

05:45 knows how to process receipts correctly next time without asking me. Although that was a very simple example, it’s the exact same process as your folders grow. For example, within our health folder, we can add the resources, projects, and archive subfolders we covered earlier with annual health reports and doctor visit notes inside resources. >> [music] >> The AI can use a rulebook, those folder names, and each file’s contents to work out where it belongs. Pro tip, you can even ask the AI to analyze the files in your folders and recommend new subfolders to create and group your

06:17 files in. For example, not to jump ahead, but this is my actual business records folder in Google Drive. And it was Claude that first created these four subfolders, and second, grouped and moved my files into these four subfolders. Put simply, the rulebook gives the AI the organizing principles, and your folder structure and saved preferences tell the AI how to apply them to your files. Now, I’ve been using this exact system for my YouTube production workflow in Dropbox with my editor. And luckily for me, Dropbox

06:47 agreed to sponsor this video. For context, I used to manually rename and upload files into separate folders for my video editor. But now, with Dropbox connected to ChatGPT work, I can just give it access to JeffOS, the folder on my computer containing my rulebook, then dump all my video files into [music] a inbox folder in Dropbox and say, “Organize the files in my Dropbox inbox for my editor using my handoff rules. Show me the plan first.” And let’s fast forward. Here, we can see that ChatGPT

07:17 proposes new names and locations for the files. And after reviewing the plan, I can just say, “Approved.” And after fast forwarding again here, we see the files are renamed and moved from the inbox into that video’s Dropbox folder. And now that Dropbox and ChatGPT has organized my files using my handoff rules, I can ask it for an email draft with the folder link, paste into Gmail, and send it to my editor. He opens one Dropbox folder, and everything’s ready to edit. To do the same with your team, click the link below to try Dropbox in ChatGPT. Thank you Dropbox for

07:47 sponsoring this video. All right, now let’s cover a more realistic example where all files are stored on a cloud platform like Google Drive and where we already have some sort of file management system in place. First, go ahead and install the Google Drive for desktop app and sign in. This makes your Drive folder available [music] in Finder on the Mac or File Explorer on Windows. And the purpose is so that we can give AI access to them, right? And any

08:18 changes you make here will sync back to your Google Drive. You don’t have to use Google Drive, by the way. This works for the Dropbox desktop app, the OneDrive desktop app, and even iCloud Drive. And yes, I know you can connect to the Google Drive plugin or connector, but to oversimplify, connecting, or rather sharing the Google Drive folder on desktop directly makes it much easier for AI to process those files. All right, back in ChatGPT work with the same folder mounted, I’m just going to click the plus icon, select my Google Drive folder, and give it access to the

08:50 root My Drive folder. And although I’m using ChatGPT work in this example, the workflow is the same in Claude. In fact, I’d say it’s even more intuitive in Claude since you can just mount multiple folders to the same chat. Go to it. Since we’re just asking the AI to look at the folder and file names to understand the structure, we do not need to make the entire Drive available offline for this exercise. The AI can still read the basic metadata. Now, before moving anything, I want the AI to give me two snapshots. First, the current state showing how my files are

09:21 organized right now. And second, a proposed future state showing how the files could be organized using our rulebook. [music] And comparing the two makes it easier to see what needs to move and where. And to do that, I’m going to use this prompt, which I’ll also link down below, to get both snapshots as readable folder trees without changing anything. You’ll see what I mean. And let’s just fast forward this part. All right, so even though I’ve done this many times, it’s still pretty incredible to see AI map out my entire drive hierarchy. Like my

09:53 top-level [music] business folder, Sushi Labs, has zero standalone files sitting directly inside it, but it has [music] 805 files total, and I can see all these subfolders underneath as well. Next, the AI flags the main structural problems, such as my business finance records living in two different locations, and [music] a quick share folder sitting at the root level, which goes against my own framework. Now, I want to be very clear. There is no right or wrong way to organize your files. Even though I follow my Area

10:23 First PARA framework religiously, I share a lot of files and [music] free templates with you guys. So, I want to keep the quick share folder in the root level for convenience, right? So, I’d write that as an exception in my actual rulebook. Back in ChatGPT work under the proposed future state section, we see the AI recommends reorganizing our files in this way. For example, under the parent Sushi Labs folder, the AI recommends five subfolders, and even though it only shows the number of files

10:54 for now, we can ask it to specify what files go where after we’ve answered the questions below. Here, the AI is asking clarifying questions, such as whether or not my accounting records should move to business finances or remain in business operations, right? And although I’m skipping these in the interest of time, when you do this, actually answer these questions so the AI learns your preferences. Obviously, your folders and suggestions will look different from mine, but the process stays the same. Give the AI access to your file management platform, ask it to map your

11:24 current state, then ask it to propose a future state using the starter rulebook. Once you’re happy with the proposal, ask the AI to walk you through which files and [music] folders to move and where, step by step. Start with area folders you use frequently and move existing folders together where possible. Ignore file name changes for now, so it doesn’t become a huge renaming project. To be clear, you could let AI make the changes, but I recommend doing this first pass yourself with the AI guiding you, so you get familiar with where everything lives. And unlike the web

11:55 version, the Google Drive desktop app makes the process super easy since we can literally just select and drag files and folders into their new locations. Pro tip, if you want to start from scratch, create a legacy folder at the root level and move all your unsorted files and folders into it. So, it’s like starting with an empty root folder. That way, you can build your new folder structure from scratch and gradually bring over what you need. By the way, the free starter rulebook I’ve linked down below is more than enough to get you started, but if you want the

12:26 optimized file management system I use in my own workspace, you might want to check out the Co-worker Academy course, linked down below. All right, once you’ve organized your existing files, let’s create a scheduled task to help keep them that way. Staying with our Google Drive for desktop example, create a 00 inbox folder at the root of My Drive. And pro tip, add this folder to favorites in Finder or quick access on Windows, so it’s easy to get to. Next, drop a few files you would realistically want to keep into the inbox folder. And with that folder mounted, ask the AI to

12:57 organize those files using your rulebook and give it feedback until the files are named and filed the way you want. I’ve covered scheduled task multiple times in other videos, so I won’t waste your time here, but basically, once you’re happy with the results, stay in that same chat and ask the AI in plain English to create a daily scheduled task that checks your inbox and proposes changes for you to review and approve. Pro tip, make sure the scheduled task runs in the project folder containing your file management rulebook and has access to

13:27 your Google Drive folder so that it can read your rules and find the files it needs to organize. Here’s a report for my scheduled run earlier today and notice there are no follow-up questions since the AI knows my preferences so well at this point. So, I just reply approved and all files are renamed and organized. After you set this up, you’ll probably give a bit more feedback in the first few days as the AI runs into new situations and learns your preferences. But after 2 weeks, the reports should be around 95% accurate with minimal input from you. By the way, if you want to get

13:58 1% better at AI every week, sign up for my free newsletter to receive one insanely actual AI tip you can apply in under 2 minutes. Link down below. As a quick recap, your day-to-day workflow should look something like this. You drop the files you want to keep into your inbox folder and the scheduled task gives you a daily report with proposed changes. You review it, give feedback, and approve. Then the AI renames and files those items for you. And when you ask it to remember a preference, it updates the rulebook so you don’t have to repeat that feedback next [music]

14:29 time. If you enjoyed this, you might want to check out my ChatGPT work tutorial next. See you on the next video in the meantime. Have a great one.