I think it's less confusing when you consider the very first thing the earring says: "better for you if you take me off". The wearer should rationally always regret not following its advice, including that first thing.
I think the paradox is here, and it comes from cheeky use of misleading language:
> ...The wearer lives an abnormally successful life, usually ending out as a rich and much-beloved pillar of the community with a large and happy family.
The wearer doesn't really live any sort of life. Once it fully integrates with you your brain is mush, you're no longer experiencing anything. At some fuzzy point in there you've basically died and been replaced by the earring.
I think the paradox is here, and it comes from cheeky use of misleading language:
> ...The wearer lives an abnormally successful life, usually ending out as a rich and much-beloved pillar of the community with a large and happy family.
The wearer doesn't really live any sort of life. Once it fully integrates with you your brain is mush, you're no longer experiencing anything. At some fuzzy point in there you've basically died and been replaced by the earring.