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I've seen similar - Them: "You're too pessimistic" vs. Me: "You haven't thought this all the way through".

There's a balance to be struck though, because often worrying too much about things that don't happen or saying "I told you so" when they do only really serves to annoy people.

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There is indeed a balance, because opportunities tend to have time limits. Thinking things through for too long to arrive at a sure and optimal way of doing something might mean failing to take the opportunity you had to do it at all.

Thinking things through isn't necessarily pessimistic. When I have a contingency plan already in mind, I worry less about the event actually happening.

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