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Someone recently mentioned that a bit of pessimism is necessary to see the 'dark side' of future roadblocks that we might not otherwise pay attention to if we were only seeing the bright side through optimism. Do you agree with this?
No. Optimism is foreseeing the roadblocks but believing you will either get through them or even gain some advantage from them. Pessimism is thinking they are bound to derail the plan.
Not foreseeing the roadblocks at all is blind optimism, akin to being blinkered.