Let AI Sort the Six Thousand Screenshots

IMG_4823.jpg is a whiteboard, photographed at a slant, from a meeting you can't place. It's one of forty whiteboards in your Downloads folder, sitting alongside a tax return from 2021, a screenshot of a recipe and something called final_FINAL_v3.pdf.

Six thousand other files keep them company, and you've meant to sort them since the laptop was new.

AI can now look at the files on your computer, see what's in a photo, read what's in a document, and then rename and move things to match. In Claude, you do this in the desktop app, after giving the app access to a folder. ChatGPT has its own version.

The mistake is letting AI loose on the real folder before you've decided what "sorted" means. Ask AI to organise your files with no instructions, and it invents its own system of twelve folders with names like "Miscellaneous Documents".

It's like moving house, where somebody writes the labels on the boxes before anyone packs. That somebody is you.

Tonight, write the labels

Spend five minutes on paper first. For most people the boxes are these.

• Photos by year, then by event or month
• Screenshots by what they show, such as receipts, recipes, things to read and things to send someone
• Documents by what they're for, such as money, home, health, work and the kids
• A "not sure" folder for anything the AI can't place, so nothing gets guessed

Next comes a naming rule, which is to put the date first, use dashes, and keep it all lower case. That way 2024-06-italy-trip.jpg beats Italy trip (2024) final.jpg.

Then pack one test box by copying fifty files into a new folder called sorting-test. Give the AI access to that folder, and run your system on it.

Here's how I want my files organised. [paste your system and naming rule] Look at every file in this folder, including what's in the photos and documents. Suggest a new name and folder for each one, as a list. Mark anything you're unsure about for the "not sure" folder. Don't move or rename anything yet.

Read the list, because this is where you'll catch the AI calling your grandmother's 80th a "group event", or filing a bank letter under "home".

Correct the list, and add what you learned to your system. For example, "receipts means anything with a total and a date on it". After two or three rounds, the list comes back right.

To sort a photo, the AI has to see the photo, and to file a letter, the AI has to read the letter. That's fine for most folders, but some folders I'd sort by hand in an evening. That means the one with the medical scans, the one with the kids, and the one with screenshots of your bank.

At the weekend, the real folder

There are two rules for the real folder. First, the AI moves and renames but never deletes. Second, the AI works on a copy of anything you'd cry about losing, because "never delete" is an instruction the AI can misread.

Apply the same system to this folder. Move and rename, but never delete anything. If two files would get the same name, add a number. Put anything you're not sure about in "not sure". When you're done, give me a summary. Tell me how many files went where. Then list everything in "not sure" with your best guess for each.

A big folder takes a while, so make a tea. Afterwards, open three or four folders at random and check they hold what their names say. Then go through "not sure" yourself.

Going through it usually takes twenty minutes, and it's where the odd things live. Think of the one photo of a document, or the screenshot that turns out to be a receipt.

Expect two kinds of mistake from the AI. The first is about dates, because the AI takes the date from the file itself. That's often the day you downloaded the file, years after the photo was taken.

For old photos, tell the AI to go by what's in the picture and mark the year as a rough guess. The second kind of mistake is about faces and places. The AI can't tell your two friends called Sam apart, and it will name a folder "beach" for a photo of a lake.

Treat the AI's names as suggestions, and let your random checks and the "not sure" folder catch the rest.

Once a month, Downloads again

After that, a scheduled task can run the same system over Downloads once a month. A scheduled task is a job the AI does by itself on a timer, and I've written about how to set those up.

Six thousand files took four years to not get sorted, because what was missing all along was a system you'd decided on. That part still needs you.

So does the last file in "not sure", a whiteboard at a slant, from a meeting only you were in.