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$10,000,000 doesn't go far enough to justify leaving work altogether. Not before having kids and still fairly early in my career with a cancer history.
I'd go back to school for an MSW and become a social worker - a career I never got the chance to pursue because it pays so little. That would provide health insurance and help me continue to contribute to retirement savings.
A lottery win would just mean I could structure my life in a way that was meaningful, rather than a way that helps me be as financially secure as possible.
My new job would be determining the best plan for giving away those millions...
learning which organizations accomplish the most, with the least overhead.
When all but the last million was given away, I'd keep that last one for myself,
"retire" from my self-employment, and do some traveling.
Nice work, if I could get it!
You are in San Francisco. How long can you live on $1million
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