 By show of hands, what are you most afraid of? I'm most afraid of outliving my money. The longer you live, the more likely it is, unless you've done really well, that you may outlive your money. You might outlive it because of a stock market crash, but you may outlive it just because you've lived too long. Let me put this in perspective. Social Security was brought out in the 1930s. Life expectancy for a man in the United States was like 65 or 68 years old.