"When this asymmetry is present, there is not a lot of margin for error for being a pessimist; quickly, it becomes an awful financial decision. This leads one to think that being an optimist by default is a superior mindset. An optimist needs to capture just a few highly successful investments in his lifetime to make a lot of money and retire. A pessimist, usually, needs to be right constantly and keep having great ideas to generate returns. I say usually because there are some examples of people that got very rich very quickly by being pessimists, like Nassim Taleb in the crash of 87, John Paulson and other investors in the crash of 2008 and big name fund managers like George Soros and Stanley Druckenmiller."
"But for every pessimist that got rich that way there are hundreds or thousands of people that got rich by being optimists, just consider that most people become millionaires by owning real estate or by opening a business. A pessimist, even when he is right, ends up hurting himself because he gets the illusion that he can be unbalanced in his mindset and that is ok. If his name isn’t Stanley Druckenmiller, chances are it isn’t ok. In the long-run, he ends up paying by missing out on opportunities. A pessimist, even when he wins, loses."
"But for every pessimist that got rich that way there are hundreds or thousands of people that got rich by being optimists, just consider that most people become millionaires by owning real estate or by opening a business. A pessimist, even when he is right, ends up hurting himself because he gets the illusion that he can be unbalanced in his mindset and that is ok. If his name isn’t Stanley Druckenmiller, chances are it isn’t ok. In the long-run, he ends up paying by missing out on opportunities. A pessimist, even when he wins, loses."