What would you do if you won a lump sum of $50MM after taxes? Forget the logistics and the chances - no one wants to hear your boring ass drone on about "the lotto is a tax for stoopid people" and "I would find a good lawyer and put my money in a trust fund first so I could claim it anonymously blah blah". Get straight to the fun part. What would I do? 1) I wouldn't live lavishly. I would just do whatever I felt like without every worrying about money again, given that 4% interest a year would give me a nice salary base of $2MM. 2) I would travel (on a budget) for 2-3 years or until I got tired of it. I'd like to visit all the continents. The only things I would not be cheap on would be excursions and drinks. Definitely would stay at small guesthouses and hostels though. Would try to pick up some languages and skills through lessons with experts. 3) I'd probably get a degree in English/writing or Psychology after that, in some place other than the US. 4) I would have apartments in NY, Tokyo, Bangkok, Melbourne, Tuscany, Buenos Aires, and Stockholm. 5) I'd probably become a novelist or a research psychologist. If the former, I would try to change the country I live in every few months or years. See, nothing too fancy. Just want the security of not having to work corporate, being able to travel, and being able to provide for a future family without worry. Edit: Whatever I did not spend of the $2MM a year I would give to some sort of NGO of my choice.