Pessimism

Sometimes people debate pessimism versus optimism as if you must generally choose one to side with in most aspects of life. Well, not only is it difficult to reach a verdict on such a big question, the fact it's difficult should be a hint that the verdict will be useless in any specific situation. Look at specific situations directly and pick an approach for each.

Actually, it's a wrong question. How did such a debate come to be common in the first place? Why does anyone care which one "wins" overall? Well, let's not care.

I've observed that pessimism should be useful for:

• The planning fallacy
• Planning around ADHD
• Correctly predicting what will happen in … most situations. It's really difficult to undershoot reality so much that you're pleasantly surprised around half the time. Seen through this lens, undershooting it to that extent still isn't more pessimistic than optimistic, it's only reached equality at that point… it just feels like pessimism because we have built-in optimistic biases and so what we wind up having to do consciously is be pessmistic almost all the time.
• Hedonism – pleasant surprises beat disappointments… though this is a standard argument in a debate that bores me, it has a standard counterargument along the lines of "well, maybe expecting so little of the future disenergizes you and then you put in less effort and then you have a self-fulfilling prophecy". For myself, I doubt that.