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Definition 1 is negative. I'm guessing so is Definition 2, because of 'stubborn' and 'regardless of the consequences'.

1. I'm flummoxed: Why? Doesn't the noun will connote positivity (its etymology: http://www.etymonline.com/index.php?term=will&allowed_in_frame=0)?

From http://www.etymonline.com/index.php?allowed_in_frame=0&search=willful&searchmode=none:

wilful = ...c.1200, "strong-willed," usually in a bad sense,...

2. What's the term for this phenomenon, where the noun is positive but the adjective is negative, and vice versa?

3. Are there other words subject to this paradox?

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  • How about ill will? I don't think in actual use will has to be positive.
    – user3169
    Aug 17 '14 at 15:25
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The meanings of a word are not constrained by its origins any more than your character is determined by that of your ancestors. The fact that your great-great-grandfather was First Lord of the Admiralty and his brother a notorious pirate does not mean that you yourself are destined either for the Navy or the long drop, or even that you are bound to a seagoing career. In the same way, words develop in different directions as they grow older, and what a word meant a hundred or two hundred or two thousand years ago is irrelevant to present-day users, who have no knowledge of that earlier meaning. To argue otherwise is the etymological fallacy.

So there is no "paradox" here. Today, will has no necessary "positive" meaning.

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