How I would spend my lottery jackpot

First, I suppose I should buy a ticket. 

That increases my odds of winning from zero to more-than-zero.

I would have a chance of winning 1.1 billion dollars, or about $650 million in the instant cash option. Or only about $400 million after tax.  

Don't criticize me for saying only.  After all, I just watched $700 million disappear. I have never lost that much money in an instant, and it takes getting used to.

First thing I would do is line up a lawyer and accountant. I have lots of lawyer and accountant friends, but I am pretty sure that a windfall of $650 million in one moment would present novel tax problems and opportunities outside their expertise and experience. I worry I might offend my excellent current CPA by finding some out-of-town lottery-winner specialist to work with. It would be the same thing with attorneys. Attorneys volunteer on my wife's Legal Services board of directors. I feel grateful to them. But again, there may be some unusual legal issues that come up in sudden windfalls of this magnitude and I may need an out-of-town specialist. So, from the get-go, I would be worried about negotiating hurt feelings.

Next, I would arrange with my wife to decide how much of it we would gift to close relatives, and how we would define that, and most important, how we would explain it. I am already imagining how I would feel if my sister or brother had the windfall of $650 million. I wouldn't expect something--not at all---but I suppose I would think it would be a nice gesture from them, what with my having helped them move a heavy couch up some stairs a year ago, and having played a lot of cribbage with them over the decades. Maybe we would give a million each to the siblings to get that out of the way. Maybe two million. We would tell them that our lawyers said that this was stretching it, and say it was for some arcane tax reason. It wouldn't be us, putting a limit on our love, I mean our money. We would blame third parties. There might be lingering hurt feelings that it wasn't more. After all, it could be more.

Then there is the setting up of a charitable trust and a mechanism for doing something meaningful with the money. My wife and I have some experience with foundations, and I don't envy the people who set them up or work for them. They have offices. Bureaucracies. Rules and criteria. We would be setting up a small business. So instead of being retired and playing with my melons, I would be meeting with lawyers and making hiring decisions. It would be work.

Then, my wife and I would need to decide how we would change our financial lifestyle. I live well, but not $400 million well. I like the house we live in. It is already too big. We might consider hiring a full time assistant/butler/house-person. That would be someone trustworthy to pick up our mail when we are out of town and someone to keep track of paying the few bills that aren't on auto-pay. I suppose I would buy a new pickup truck. I absolutely would have the new house-person get the truck washed every week or so. That would improve my life. I would feel wasteful about flying business class, when I really do fit into the economy-plus seats perfectly well, but I would spring for it. Business class is better than coach. That's all I can think of.

It might be nice to have the development directors of local charities be nice to me, but they are already nice to me and I only have peanuts to give them. Now they seem happy when I donate the pittances I can afford. If I had the interest off $300 million dollars to give away--maybe $15 million dollars a year-- they would feel disappointed if I only gave them a million dollars here and there. Oh, they would be happy for it but maybe a little disappointed, too. A million dollar gift meant that some other charity got money I could have given them. I don't blame them. 

Mostly I worry that it would spoil our children. It would be hard for them to buckle down and build satisfying careers knowing that there is a boatload of money waiting for them. (I wouldn't buy a boat; that would just be more hassles.)  It would be hard for them to feel the satisfaction of getting hired for a job, making a boss happy, and getting a promotion from clerk to assistant manager if one's parents were giving away money every couple of days in amounts equal to their annual salary. Why bother working if the money involved is essentially meaningless? 

I suppose I could hire the adult children to help run the foundation, but that would put them in the pathetic role of a job being in service to one's parents. They never really grow up. Look at poor Prince Charles. Pitiful. 

Politicians would expect bigger gifts from me. and I would make some of them. I already get phone calls from candidates I have never heard of in faraway places. That would be a nuisance and they would all know I could give money if I really wanted to. Now when I tell good candidates I am tapped out, they believe me, so are happy with whatever I give them. Once again I would spread disappointment.

Almost everything about winning the lottery would make my life worse. I may not buy a ticket.

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[Update: My brother read this post earlier today and he said that he, too, had been having a similar revery about winning. He said that in his revery he planned to give five million dollars to each of his siblings--not my measly one or two.]