Strategies for Organizing a Messy Hard Drive?

Personally, I embrace this, I have some structure, where I put stuff long-term, like pictures / documents / movies / music / code Everything else gets to live in the Downloads and Desktop folders, and they get to be copied into subdirectories indefinitely, by year.

And honestly, I think it's great to take a stroll through my history, I end up on the lowest levels, my C:\ drive from the DOS era, along with directories of backups of floppies.. It gives me an idea what life was like back then, who I was, how I thought about things.

Storage becomes cheaper every day, and the data from back then is so insifnificant, the first 10 years of my computing fits comfortably within what capacity a new version of Firefox takes up.

SO yea, I don't delete stuff, almost ever. Maybe I'll go shoot a few Ubuntu ISOs once in a while, but all in all, everything gets to stay.

Oh the horror and joy of seeing which gifs 14 year old I decided to download off of IRC :D

Delete "Downloads". Everything in there is probably outdated (or soon will be) and can be downloaded again anyway.

Move the clutter to a folder in your cloud storage account. Configure that folder so it doesn't sync to your local device(s). In a few years you'll wonder why you still keep it around.