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katydee comments on The Problem of "Win-More" - Less Wrong Discussion
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Can you give additional example of this? I'm looking for parallels elsewhere in life where something is apparently useful, but is only useful in cases where you don't really need it, and nothing leaps to mind.
Picking individual stocks, being wary of "concern trolls" on the internet, making big elaborate complicated plans.
The last one is the only one I understand from your list, but it seems like a rather good concrete example. Making an elaborate plan is a great idea if it's definitely going to be useful, but otherwise it's a waste of time - like in HPMOR, when Harry makes a whole scheme of experiments to do that'll last for many months, but then it turns out his most fundamental premise is totally wrong. The big plan give him a big win when his assumptions are correct, but don't help him one iota when they're wrong, and he wastes a lot of time.
Moral: only make large schemes when you have strong evidence that they'll be very useful, and even then, first carry out any basic preliminary research, to check the assumptions going into the plan.
On #2 - Oh yes. Actual concern trolling is less common or harmful than dismissing actual ally concerns.