The short of it is that you have to strike a balance between ease of use and security, much of the time, and decide what provides the optimal level of both for your purposes.
An excellent case in point is passwords. The easy way to go about it is to just have one, use it everywhere, and make it something easy to remember. The secure way to go about it is to have a randomly generated variable-length sequence of characters across the encoding spectrum that only the user himself knows.
Naturally, if you go too far on the easy side, the user's data is easy to pick off. If you go too far on the side of security, however, practical application could end up leading to situations that compromise the added value of the security measures (e.g. people can't remember their whole keychain of passwords and corresponding user names, and therefore write them all down somewhere. If the list is compromised, the security measures that had been put into place are for naught. Hence, most of the time a balance gets struck and places ask that you put a number in your password and tell you not to do anything stupid like tell it to other people.
Even if you remove the possibility of a malicious person with the keys to everything leaking data from the equation, human stupidity is infinite. There is no such thing as 100% security.