If I Won the Lottery: What To Do?

When I divorced, my financial advisor urged me to use my debit card for all purchases so I would never charge or overspend. The goal was to rebuild my nest egg. More than 13 years later, the habit has stuck to me like a post-it note. It’s a constant reminder not to carry real cash that just takes up room in my wallet. 

However, on days when I have a few loose dollars, I find it hard to resist buying a lotto ticket or two—for which you have to pay cash. What the heck. The thought of winning boosts my endorphins like a chunk of dark chocolate. Yet, there is some thought behind my purchase. I always wait until the pot is significant—exceeding $100 million—and buy my tickets at some out-of-the-way locations, the kind of places that seem to produce the jackpot winners. 

When Power Ball and Mega Millions had soared beyond that mark the other day, I purchased two tickets for a paltry $3 total. And then the fantasies began churning. I, like other incredibly naïve folks, began thinking that I had a realistic chance of winning. Well, I do until I don’t but here goes my thinking about how I would spend half of, say, $100 million since the rest would go to pay the taxes: 

• $2 million to each daughter for real estate purchases and $1 million to each to invest. I like Warren Buffet’s idea that he didn’t want his children to stop working if they thought they were in for a windfall. You’ll thank me some day, girls, that I didn’t give you more.
• $3 million set aside for grandchildren’s educational needs with $2 million for the two boys already born and $1 million for the unmarried daughter’s future child. If she has a second child, we’ll worry about playing catch-up later. I’ll just try my lottery luck again.
• $1 million to the beau, who really deserves about $10 million for putting up with me after I broke my hand. If I give him too much, he might leave me, so just enough to keep him around is my theory.
• $1 million to my almost 98-year-old mother who really doesn’t need anything but likes to give us gifts with a “warm hand.” With this windfall, she’ll give us bigger gifts that we won’t need for we’ll be spending our windfall. But thanks, Mom, in advance.
• $2 million split among my closest pals and a few relatives (you know who you are), who are in need,  have been loyal through my divorce and listened to those stories probably 100 times of “I can’t believe he did this and that!”
• $6 million for two new homes with one in an urban location and the other in the country. I’m not into megabig just large enough square footage, nice eat-in kitchens, which I now don’t have, and maybe one ocean view.
• $2 million for my alma mater so I can set up a professorship and a chunk, maybe $500,000, to my daughters’ high school, which gave them a love of learning.
• $1 million for my town’s library, which has provided “daycare” when my mom visits, doesn’t scold me when I return books late, and is part of the soul of my bucolic village. This isn’t a payoff with a stipulation that it has to keep my books on display in cabinets at the front---though that would be a really nice thank you.
•  $2 million for me to invest so I can spend less time on writing articles I don’t like though I plan on continuing to work, just like all the other Lotto winners pretend they’ll do and then quit the next day. I won’t; you read it here before you heard it on the evening news.
• $10 million to fix some of the pot holes in New York City, which have been ruining my car every time I drive into the city. Former Mayor Bloomberg should have but he probably never drives himself and notices or his car is so expensive that he never feels the bumps.
• $2 million to give up  my cars and hire Uber or Lyft drivers all the time so I don’t have to deal with potholes, deer crossing the road, and road rage.
• $2 million to invest and use for travel, though I won’t be obnoxious and only stay at Four Seasons and Ritz-Carlton hotels, except for one time to see what some folks are paying for. I’ll definitely buy something from the minibar. And I’ll  upgrade to business or first class staying on the special club floors with all the food, drinks and other amenities.
• $1 million toward ordering take-out and having a personal chef and maid since a recent New York Times article stated that people who do are happier than others.
• $1 million for new clothing, regular hair coloring, highlights, weekly blow dries, and more pedicures from places that pay their staff full “living” wages. Or at least I’ll be able to tip more generously. I may try some of the most expensive creams that remove wrinkles since I know that I don’t want elective surgery such as a face or neck lift after the trauma of surgery for my recently broken arm. I do need to look the part of someone rich, a style I’ve never tried. And yes, Daughter No. 1, I will buy that Chanel purse you said I should own by this age, though you know I won’t carry it since I dislike labels. It’s YOURS!
• $500,000 for adequate therapy since I will need to remain grounded and probably should discuss with a professional how I came up with these numbers and recipients. 

And I promise not to fall into the usual rut of most winners who blow all, become instantly poor and are miserable.