A few weeks ago, my (newly) 18-year-old daughter was excited that on the first day she could buy a lottery ticket, the jackpot was an unheard-of ungodly amount, like $300 million or something. Of course, I bought a ticket or two myself.
My late mother frowned on gambling, and considered the Lottery gambling. My comment to her once was "Anything that takes my mind off my problems, and makes me smile thinking of spending this money can't be bad."
My thinking on how I would spend that money hasn't changed, much, anyway. With any big payout (over $100 million), I would first pay the debts, then I would establish a trust for each of my kids. They would get money as long as they held a job. I don't care what job, they just need to work. I would hope they would work a non-profit, but that would be their decision.
I would take a big trip--like 3-4 months. Rent a place in Italy or France and just relax and drink some good wine and eat some good food. Maybe bring some friends for a while. Poke around shops. Buy another bulldog. Some me-and-Joe-and-kids time.
I would establish a scholarship at UNC for a high-school kid who had decent-enough grades to get accepted, but worked all through high school. In my house right now, none of my kids are eligible for any need-based scholarship, and (because of our values) were forced to work during high school, interfering with the time they put into school. I don't delude myself and believe that if they didn't work, they would have done better in school, but the argument is that they could have. Anyway, paying for their college in full has been a bit of a stretch for their dad and me, not so much now, but in the retirement we could be putting away. Choices, you know? So, the scholarship would help someone, or more than just one student, who has worked, earned decent grades, and would put a hardship on their family to pay for school. If the Lottery were large enough, I might establish the same scholarship at University of Kansas, but maybe not.
I would figure out how to have an account that would hold enough money that The Lord's Diner (a "restaurant" in Wichita serving a hot meal to anyone who comes in) could buy food from the interest. The Lord's Diner is a great concept, and I appreciate that it is staffed by only a few people, and everyone else is a volunteer. It was begun and initially funded by the Catholic Diocese of Wichita, but nearly everyone in Wichita has a night to serve: churches, both Catholic and Protestant; businesses; schools; sororities and fraternities;--you name it, the group has most likely signed up for a stint working.
I might buy myself a new car, but maybe not. I do love my little Caroline-blue Beetle.
So, what would you do with a Lottery windfall?