The Real Abed
Perma-Junior
Sounds like you have a bigger problem to figure out.I'm perpetually at the "startup drive almost full" stage, no matter how much I delete. 5GB, 10GB, 20GB freed - it doesn't matter, Mac OS finds a way to fill up that space without me knowing it before a week has passed.
What's it filling it up with? Cache files? Check the usual cache folders:
/Library/Cache/
/System/Library/Cache/ (Not as easy or recommended to empty out)
~/Library/Cache/
Then there's other more hidden ones like the Private/Var/Folders/whatever cache that you can delete if you know where it is, but it can cause non-harmful problems.
Look in those folders and see if there's any abnormally large ones. (Don't worry about deleting anything in the normal cache folders. It'll just be recreated when needed. But if you do delete, reboot right away before emptying the trash just so apps can "release" the files and you won't encounter any "file is in use" errors. Then empty it when you boot back in.) If something is really big, and it really shouldn't be, especially 20GB or something, then that's the culprit.
First find what's using the space. Because if your OS is constantly filling it up, and you're not downloading a lot of big files and keeping them, then something is wrong. Maybe a rogue application. (Didn't Spotify have this problem a while ago?)