How can I anonymously share a USB stick with files?

If you're willing to go the extra mile to maintain anonymity, you could use something like the Tor browser to create a temporary email account for sending the files. But remember, the anonymity could diminish the impact of your message. It's possible your management already knows about the issues at hand. Just keep that in mind before you take this route.

Realistically, though, anyone might just throw away an unknown USB. Printing might be simpler and more effective in the long run, just to avoid all the tech hassles.

Using a burner email account through a secure service could also work. Just make sure the username has nothing to do with your real identity. If you think your company's email might block accounts like ProtonMail, maybe it’s better to print everything out instead. That way, you're definitely staying away from any digital traces that could lead back to you.

If you really want to keep your identity hidden, an extreme option would be to consult with a lawyer to communicate on your behalf. But that seems like overkill for just trying to improve work conditions, right?

Honestly, just printing the documents might be a smarter move. People are unlikely to plug in random USB drives they find, especially at work. You could also add a cover sheet with an index to keep things organized.

Here's a solid approach: First, use a service to strip any metadata from your files. You can try something like metadata2go.com to delete any identifiable details. Next, get a brand new USB stick since old ones can have recoverable files. Check each file carefully to make sure there's no personal info; if there is, use an editor to redact it. For delivery, consider sending the USB in a plain envelope, using a printing service for the letter so it doesn't look like your handwriting. You could even drop it off when people are out of the office, but be sneaky about timing!