I suppose I should start somewhere. I am a pessimist.
Personally, I don't understand why anyone isn't a pessimist. And I think most people already are; they just don't know it yet.
The pessimist expects the worst, and makes due preparations. They anticipate failure and mercilessly scrutinise every contingency for possible holes.
Now, don't mistake pessimism for abjection. The pessimist does hope for the best, just like everyone else. The difference is that they don't expect it. They hope to pass their exam, they think, "Oh, wouldn't it be nice if I won the lottery". But they don't base their lives on it. The pessimist hopes for the best, but prepares for the worst.
The obvious exception is when it's a sure win. When I was getting my GCSEs and A-level results, it never crossed my mind that I would get anything less than an A in Maths. And I didn't. Anticipating a success doesn't make me any less of a pessimist, it just means that the worst is so unlikely that preparation for it would actually be detrimental in itself.
Now, consider the optimist: they see the glass as half full. They inevitably think they have more than they actually do, over-estimating and rounding up. To them, a success is anticipated, so there is less pleasure when it occurs. They can rarely be pleasantly surprised, because they are always anticipating another good thing. They can be unpleasantly surprised, however; the optimist gives people the benefit of the doubt, so does not expect to be mugged. Sadly, a perky attitude doesn't help that.
The pessimist, on the other hand, never expects a pleasant surprise, so is all the more pleased when a nice surprise does happen. Consider a surprise birthday party: the optimist assumes one will happen, while the pessimist assume no one will bother. The optimist, then, can be either vindicated or unpleasantly surprised, while the pessimist can be either vindicated or pleasantly surprised.
I know which two options I would rather have.
A common objection to pessimism is that it's a negative feedback loop: being pessimistic will cause bad things to happen, causing feelings of depression and sadness. This leads to more pessimistic behaviour, which causes more bad things to happen, which cause sad feelings, which cause more pessimistic behaviour, which... ad infinitum.
As I've already pointed out, pessimism is beneficial in that it neither causes bad things to happen, nor does it engender negative emotions when they inevitably do. If anything, it acts as a buffer against such emotions: the bleeding-heart optimist may be passionate about life, but passion swings both ways, and bad things will hurt them twice as hard.
So that's why I'm a pessimist: it's pragmatic, frugal, and buffers you from depression.

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