I'd put it in an investment fund, then use the dividends and returns on investment to pay for my life. A good mutual fund can make 8% a year, so assuming millions means ~5 million, that's $400k a year return on investment. Federal capital gains tax is ~15%, plus ~10% CA income tax. So -25% = 300k a year. Plus a job at $200k a year (minus CA tax @ 11.3% & federal @ 35% = ~107k), that's a solid $400k a year riding solo. No complaints there.