This is where diceware comes in. You are supposed to pick whatever word you roll on the first try, no exceptions, for this very reason. Rolling until you get a word you "like" reduces randomnesss significantly. They even say you should use
only use real, meatspace dice to generate passwords to be truly random, not pseudorandom.
http://world.std.com/~reinhold/dicewarefaq.html
>There are some obscure words in both lists. If you passphrase includes a word you don't know, look it up in a good dictionary. Learning the word's meaning will aid you memory and your vocabulary.
Of course there's exceptions when you should start from scratch.
http://world.std.com/~reinhold/diceware.html
>Because some words on the diceware list are two characters or less, you can get a very short passphrase. If your passphrase, including the spaces between the words, is less than 17 characters long, we recommend that you start over and create a new passphrase. You should also start over if your passphrase is a recognizable English sentence or phrase. (These situations are extremely rare.)
(If it were me I'd just keep adding more and more words if my password was 17 chars or less)