According to Osho, a pessimist is simply an optimist whose hopes have soured—an optimist standing on his head. After repeated disappointments, he stops counting roses and starts counting thorns, seeing mostly nights instead of days. Optimism and pessimism are one spectrum; real freedom is to transcend both through witnessing, neither hoping nor despairing.
It’s someone who once hoped too much, got let down, and now only looks for the bad—Osho says the wiser move is to just watch life without calling it good or bad.