<prompt> Human: After age 21, if you take cash payments and dont report the income up to the maximum - see below in your best years, you may be reducing your social security benefit. Social Security calculates your average indexed monthly earnings during the 35 years in which you earned the most. Income has to be reported to figure into that calculation. In June 2011, the average Social Security benefit was 1,180.80 per month. The maximum possible benefit for a worker retiring at age 66 in 2011 is 2,366. But to get this amount, the worker would need to earn the maximum taxable amount, currently 106,800, each year after age 21. This is an oversimplification since it doesnt consider spouses benefit. You have to consider if paying the income taxes now is worth the added social security later.  <response>: If you do the math on the money you kept vs the money youd get out of Social Security I dont think youve screwed yourself at all: Youll likely have even more money if you invested it yourself. Its that pesky part about ending up in jail for breaking the tax laws Id be worried about. I guess that could be an alternate retirement plan... 