How much money would you need to never work again?

[Bunnahabhain]

29. Work is mandatory and = what you have to do in order to survive.

If you can survive without showing up at a job it's not work but rather something you have decided to occupy your time with.

For those kicking in Social Security I would remind you the maximum benefit this year is for someone that does not start collecting until they are 70, and has hit the SS cap contribution every year for many years, and it's 3.35k or 40.2k per year. Few people wait until 70 and few people have earned the cap the required number of years. http://ssa-custhelp.ssa.gov/app/answers/detail/a_id/5/~/maximum-retirement-benefit

Most financial planners will tell you 4-5% "spend rate" is safe. It will allow you to weather the ups and downs and grow your nest egg to allow for inflation. So $5 million gets you a "safe" income of 250k per year, in 2013 dollars. Also keep in mind your taxes will change. They will go to being more Mitt Romney style as you're looking at capital gains and divided income not wage income.