I don't buy individual lottery tickets, but I do have a lottery subscription. It's good for six months at a stretch and I'm automatically entered in every drawing during that period. At the end of the six months they send me a check for my winnings (if any), and then I renew my subscription. Usually I don't win anything, but I have won four or five bucks a few times and once I won fourteen. I know, I know -- lotteries are essentially a tax on people who are bad at math (guilty as charged), but I don't care. If nothing else, being able to dream about winning is worth the cost of the subscription.
I've spent a good deal of time daydreaming about what I'd do if I won. First, I'd pay off all of mine and my family's debts. Then I'd endow two trusts -- one to cover all my family's medical and educational expenses for hopefully several generations and one to make charitable contributions (kids and animals mostly, I'm sappy like that) and fund a couple scholarships at my law school alma mater.
I'd quit work and take everyone at the office out for a big fancy lunch somewhere, complete with a fleet of hired limos to chauffeur us there and back. Then I'd hire a firm of naval architects to design me a yacht that looked like a millionaire's pleasure craft from the 1930s, but was state of the art with the latest in technology and comfort. I think I'd call it the Vagabond Prince. This next part is where my detail-obsessive lawyer side comes out -- I'd set up a corporation or LLC to contract for the yacht and be responsible for employing on the crew to shield my assets and protect me from liability and I'd set off on an around the world cruise that took however long it took. I'd take loads of photos and make notes with the goal of getting a coffee table book of my trip published at the end of the journey. I'd have a website too that would include a map with real-time positioning data and webcams so you could see where I was. I'd post a few photos and notes too just to whet people's appetites for the eventual book.
Hopefully doing it this way would mean I'd be able to consider it a business venture rather than a pleasure cruise and maybe write off a portion of the trip as a business expense. Tax law not being my forte however, I'm not sure about that part. I'd have a personal assistant/operations manager that would take care of port clearances and logistics and all other administrative details so that I would only have to worry about deciding where to go next and how long to stay there.
The first leg of the voyage would be from DC down to Miami and I'd invite my friends along and it would be one big floating party. Then I'd charter a plane to fly them back home from Miami and I'd set off on my circumnavigation of the Earth. And that's what I'll do if I win the lottery.
What would you do?
(Taken with my Nikon Coolpix S200)
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