I think you are overstating the case. You are only toast on this situation and many other situations defined as "easily guessable" if and only if the attacker

I think you are overstating the case. You are only toast on this situation and many other situations defined as "easily guessable" if and only if the attacker has unlimited attempts at guessing your password. Most every system locks you out after X incorrect password entries, and X is cryptographically very small. (i.e. less than 10) As such, this would only be the case if the cracker has access to the raw password file and can make off-line guesses.