The hardest thing about being philosophically pessimistic is that people, as a rule, are so fatally optimistic, you're still likely to undershoot.
Conversation
The second worst thing is that people always confuse it with dispositional pessimism, and act as if it is.
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"Gawhd, why are you always complaining? It's like you think we should all crawl into a closet and die."
"Well, no, I enjoy life quite a lot, I just-"
*eye roll*
(Of course, communication style plays a role here - but so do expectations and stereotyping and optimism addiction.)