Great answers so far, great question, great thread.

First I'll comment on "does all this junk I'm asked to do really make a difference." Let's look at how to make a hard-to-guess password, and start with some EASY math.

If you could only use digits 0-9 for a password, the number of different passwords for a given password length is (10^3) -- OK stop stop stop, math is scary. No, let's say you could only have 3 digits -- 10 to the 3rd power, or 10 * 10 * 10 - picture this -- 0-9 (10) TIMES 0-9 (10) TIMES 0-9 (10). 1000 combinations.

If you make that more complicated and have 0-9 plus a-z plus A-Z, you have 10 + 26 + 26 = 62 different characters, to the power of whatever the length is.

Obviously, however complicated (what characters are allowed) and the length of the password both factor in here. (OK, giggle ladies, length is important ha ha)

What's not obvious is that length is more important than variety; 10^5 (100,000) is bigger than 5^10 (9,765,625; that's 97 TIMES more complex, get a calculator out and check).

So ... making people use crazy letters and symbols is basically stupid. Using a "passphrase" is basically really smart. In other words "Oy, my aching left foot" is way better than "#4fTTg6Q$%" and it's a lot easier to remember.

Here's another thing that may make IT people mad. Forcing you to change your password is STUPID. The only "attack" that helps against is if someone steals the password file. They should KNOW if the system was compromised, then force everyone to change their password. Unless someone gets the password file and cracks it, your 14 year old password is just as secure as it was when you created it. It's math.

What does this all mean?

Use a password generator anyway, and if your employer blocks things like 1Password and Lastpass (I prefer lastpass), they're stupid and oh well, find a way to work around it, like copying and pasting on your phone, or using Pushbullet, or some of the other GREAT ideas people have shared.

Now go make your passwords LONGER and easier to remember, or use a tool to make them equally long and impossible to remember.