You open a folder and there are 50 PDFs called things like `scan001.pdf`, `Document (3).pdf` and `attachment.pdf`. You need to rename them. The thought of clicking each one is paralysing.
Fifteen minutes, a couple of tools, and a system to never let it happen again.
Sort by date modified first
Don't try to rename in alphabetical chaos. Sort the folder by date modified — the order tells a story you can use. The PDF from June 14th is probably the receipt from the Italian restaurant; the one from June 21st is the airfare.
Knowing what each PDF is, even roughly, is half the work. Sorted by date, your memory does the heavy lifting.
Open each in Flint and use the title page
For each PDF, glance at the title page in Flint's editor. Five seconds tells you what it is. Rename in your OS to `YYYY-MM-DD_<context>_<doc-type>.pdf`.
For 50 PDFs at 15 seconds each, you're at 12 minutes. With breaks, 15. The investment pays back in every future search.
Use OS batch rename for patterns
If many files share a pattern (e.g., 30 receipts from the same merchant), use your OS's batch rename: macOS Finder's 'Rename', Windows Explorer's bulk rename, or PowerRename. Apply a pattern across the matching group.
This won't replace per-file work for unique documents, but it shortcuts the repetitive bulk.
Set up the habit so this is the last time
Going forward, rename on arrival. The five seconds you spend when a PDF lands saves the 15 seconds you'd spend later (plus the 30 seconds of remembering what it was). Set yourself the rule: no PDF goes into a folder without its proper name.
Within a fortnight, this is reflex. Within a month, you can't imagine working any other way.
FAQ
Can I automate PDF renaming based on content?
Some tools attempt this with OCR and keyword extraction. Results vary. For most professionals, a 5-second manual rename is more reliable than fighting an automation that gets it wrong 20% of the time.
What if I don't know what a PDF is without opening it?
Open it in Flint — the first page tells you 95% of the time. Quick previews in your OS also help.
Should I delete duplicates as I rename?
Yes, but cautiously. If two PDFs share a name pattern, check both before deleting — they might be different versions or different files with similar dates.
What's the ROI of all this renaming?
Average 25–40 minutes a week saved on searching, for a one-time cost of 30–60 minutes of cleanup. Pays back within a fortnight.
Fifty PDFs is a one-sitting cleanup. Open the worst folder in Flint and start at the top. You'll be done before lunch.