My dear friend, Kalleigh, wrote a post about what she would do if she won the lottery. I’m not one to pass up a chance to fantasize about the good life, so I decided to write about what I’d want to do.
Paying off all of our bills (including our mortgage!) would be awesome enough. However, having millions and millions to do other things with? I could hardly contain my excitement. Unlike Kalleigh, I wouldn’t really care if my friends and family knew. They’d have to know cause I’d quit my job so fast their head would spin.
I have always been of the mind that if I ever won that much money, I’d have to give some to my close family. I’d just have to. They mean too much to me that I couldn’t possibly enjoy it knowing they were still toiling away at jobs they hated whilst I was out traveling the world. Then, it always starts spinning in my head . . . where do I draw the line? I’d want to give money to my mom and dad and my siblings. Then I think. . .”but will Grandma and Grandpa be mad? Don’t they deserve a little cash? What about Aunti Chic? We used to be really close, but not so much anymore. I know she could really use the money, though. Am I being selfish?”. Suddenly, the idea of NOT telling people seems like a good one. Still, my dream life includes a world where I could spend endless time with my sister and nephews, so they would need to be taken care of.
I figure it would a year before we would start to live a normal life. Once we got the money, we’d have to set-up trusts, pay off bills, pay taxes, do the gifting, start investment accounts, adopt some charities . . . that alone would take forever! Then, I would want to travel. I could finally go to London, France, Ireland, Spain . . . it would take awhile to hit my main lists. Eventually, there will be quite a few places I’d like to go, but I would save that for quarterly travel.
My sister and I would have to decide where we want to live (I guess Michael might gets a say, as well). Somewhere with stellar programs for Matthew. We can buy a little space for Dawn so she can set-up her pastry shop. I would spend my time over-seeing the boys education and writing. Not sure what I’ll be writing, but I’ll be writing.
Ed’s school will be paid for (finally, that’s been stressful lately) and he can enjoy the experience, maybe spend a semester abroad.
My mother could stop worrying about money, pay off her mortgage and take a few trips to far off places. Maybe it will help make her sane.
I imagine my dad and Audrey heading off to Tanzania for a year. I’m sure they’d give some of their money to Aud-mo’s mom, who will be like a charity in herself-that woman can make good happen like no one I’ve ever seen.
Joe. Do you think 20 million could buy me back his love? (What? I know this is supposed to be a fun, happy post, but I can’t just NOT mention him. He’s part of it whether he fucking likes it or not) Joe would want to buy a house. He’d take his pals and travel around. I am quite certain he’d be arrested. Once he settled down, he could find himself. Maybe he’d find me.
Hmmmm, winning the lottery, oh how fun it would be. Sure, things may not pan out how I imagine, but just imagining can be fun.
I guess I better go buy a ticket!

I’m glad I gave you inspiration instead of the other way around for once!
My dilemma with giving money to loved ones – especially the younger ones – is that it might do them more harm than good. I’d want everyone to be able to find joy in their work, but still work (or have the education and ability to work in case the money ran out). The idealist in me thinks, “wow I could send my son to Harvard,” but the realist in me thinks he’d know how much money I have, wonder why he has to bother with school at all, think I’d bail his ass out of any situation he got it into, and never take responsibility for himself again.
My Guy Girlfriend once spoke about a TV show he watched that tracked down lottery winners five or so years later. Winning the lottery had ruined so many lives, split up so many people … it was sad. I’d rather keep life status quo and just kick the quality up a notch while toning the financial worries down.
Here’s hoping one of us wins something! (Actually, I won $2 on a $2 scratch off ticket … does that count? My Honey says it does and I should claim it on my taxes but I think he’s just joking … I hope …)
You’re totally right about the younger ones . . . I thought that about my brother Ed (which is why I didn’t write about more than paying for college). It’s a fine line. Although, that kid already looks to me to fix everything.
Yeah, I’ve heard HORRIBLE things about Lottery winners. Many of them end up bankrupt!
Still . . . it’s fun to dream! I needed that today, so thank you!
Sometimes when I can’t sleep I play my “lottery daydream”. I can’t get much farther than paying bills & quitting my job. But if I ever win – I will be sure to do it justice!
I bought 2 tickets last Friday – the jackpot was too huge to pass up! I never buy tickets either, but once I did I did exactly what you did and fantasized about what I would do with that amount of cash. But alas, I didn’t win and the daily grind continues.