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Some winners dream of being free of work forever. Calculating the cost to do that is tricky. Say you're 30 and need $100,000 a year to live comfortably. The average life expectancy in the U.S. is 78, so you'll need 48 years' worth of that amount, adjusted for inflation. At a 3 percent inflation rate, today's $100,000 would have to be $413,225 in the year 2060 to maintain purchasing power. It would have to be only $203,279 in year 2036, when you're at the halfway mark. You'd also expect to invest some money to counteract inflation. This is why getting good financial advice is so important.