Well, if you found this page and are interessed in pass, you must already have your reasons to look into password managers. For me, it's a basic concept: Use password only once. Don't (ever) reuse passwords or passphrases for other services. If one service gets compromised, you won't automatically have to worry about your other services. This makes remembering passwords a bitch, especially if you don't iterate through numbers of your favorite, easy-to-guess, passwords. Speaking of which, yes, there are tools out there, that can generate very good dictionaries based on a bit of social engineering. So you really should use generated passwords.