[pjdemers]

5 million before taxes is 3.5 after taxes (probably less). If you want to stay in the bay area, another million goes to a reasonable house (probably more). That leaves 2.5 million. For anyone under 50, a reasonable withdrawal rate is more like 3%, or 75k per year. Taxes and MRO on your house are at least 15k per year. Private health insurance for a family is at least 30k per year. Which leaves at most 30k per year for everything else. Plus, if you have a family, there is still college that needs to come out of the 2.5 million at some point, so the "everything else" budget will go down into the 20s. And last but not least, social security is based on last few years wage earnings, so, by the time you are old enough to collect, you will only get the minimum having not worked for a decade.

I think I would keep working.