01 September 2009

Winning the lottery, no whammies!

By: Jessica B.

Sometimes I love to daydream that I quit my job to run off to Europe and live a luxurious, adventurous life, but I always realize that this dream is contingent on one thing: that I win the lottery.

Problem with that part is that I’m not really a regular “lottery player” or gambler. I have no idea how to play slots (shocking but true) and don’t buy weekly lottery tickets.

But I will walk to a gas station and buy a lottery ticket when there is a huge jackpot because, why not? Sure, my odds of being struck by lightening are better than winning, but it’s fun. The Mega Millions jackpot was $330 million or something so Friday night I went to a gas station and bought three tickets.

And while I didn’t win (and have been at work all week), I always let myself daydream a little bit about what would happen if I did win. It was a hot topic one day at lunch too.

So here is what I would do with $330 million (or whatever I get after taxes):

  • Buy my parents house and give them a lump sum of money to cover property taxes for the next 20 years
  • Let my dad retire and say “f*ck it” to his job
  • Buy myself a SWEET condo (lots of room to walk around naked)
  • Work freelance and go back to school for my MBA
  • Donate a lot of my clothes and replace them with beautiful things from JCrew, Anthropologie and Nordstrom
  • Two words: Chanel quilted
  • Donate money to local charities
  • Volunteer more
  • Stalk Oprah.com to get tickets to a taping (since I won’t have to work)
  • Get a car, or two (and a parking spot)
  • Send my parents to Europe (and get some nice non-addictive, Michael Jackson sleeping pills for dad to help him not go crazy on that flight)
  • Travel (hi five-star hotels around the world) and take my closest friends on a nice trip
  • Buy a real pony (not that I don’t love my birthday ones, but you know, get a real, live one to love forever)
  • Get a dog (and pay someone to train him, kidding?)
  • Have fresh cut flowers in my house weekly (I LOVE fresh flowers)
  • Go to LA and stalk John Kraskinski (kidding?)
  • Get a personal trainer and get my fat a** back in shape
  • Hire a cleaning lady (I’ll be honest, I’m lazy and hate scrubbing floors)

As you can see, some are more realistic than others. And it seems I’ve put more thought into this than I imagined :)

What would you do if you won the lottery? Feel free to shoot for the stars (and get creative too!)

Edit: I also meant to add about getting a condo that I’ll have room for Alexa to come live in my “room of awesome” :) FORGIVE ME Alexa!


  1. Cheryl says:

    I want a cleaning lady. That might be my birthday present to myself…just one session but still.

  2. Rebekah says:

    Eddie and I love the lottery conversation, especially when we’re drinking. It often involves things like a cabin in Michigan, a place on Sanibel Island, laser hair removal, and a payoff to his brother so he is never allowed to ask for money again.

    We won $100 on a scratcher ticket the other day, so the good karma is headed our way!

  3. blaez says:

    Joe and I play it occasionally. He bought himself a few tickets for his birthday the other day (his bday is today Sept 3).

    We talk a lot, maybe too much, on what we’d do if we had that kind of money. 1st thing would be to pay off our debts and then the debts of our parents (if any) and make sure they can live comfortably for the rest of thier lives.

    Next would be a modest donation to our siblings.

    Then we’d buy a house and our dream cars and then more practical cars and hire someone (after extensive background checks) to take care of our house while we were off jettsetting and seeing the world.

    And more and more ofcourse… but those are the basics.

  4. jen says:

    pay off student loans, give my rents & bro a bunch of money, fly first class all throughout europe, buy a lakehouse and boat….

    i think that would cover my winnings! fun to dream about :)

  5. Kendra says:

    I want to travel around the country in one season and hit all the baseball parks. I think that would be awesome, but oh so expensive!

  6. mandy says:

    I always play when it gets really high too.
    I would pay off my student loans, buy a huge RV to drive cross country and visit all my blog friends, buy a ridiculously large amount of land and build a house right in the middle of it, quit my job and go back to school, take a great trip with friends, with that much money the possibilities are endless.

  7. barbetti says:

    Honestly…after I did the typical stuff: put up trust funds for my kids, invest, pay off family mortgages and leins, purchase nice cars and vacation homes… I’d probably hold a crapton of giveaways on my blog! And I’m lazy enough to not ever want to work again.

  8. katelin says:

    sounds like some perfect purchases to me. i’d definitely help you stalk john :)

    man i wish i could the lottery too, have a kick ass ridiculous wedding, invite all my bloggy friends too, that would be superb. and then travel the world for a year or so, man that would be nice.

  9. MinD says:

    I’d pay off my student loans before anything else. 50Gs is a lot of money that I’d like to see disappear.

  10. Lil' Woman says:

    If I won the lottery I would have the biggest freaking blog meet up ever! :)

  11. Kate says:

    Frankly, Jess, I’m stunned you’d want to keep working. Guess you make up for my inherent laziness because there is NO WAY I’d continue working on any kind of regular basis. :)

    The dream is for me and Brian to (a) quit our jobs, (b) buy a yacht and (c) spend our days boating around the world all while snorkeling as much as possible and dining on all sorts of delicious foods wherever we choose.

    Not that I’ve given this a lot of thought or anything.

  12. Nora says:

    If I won the lotto:
    Buy a villa in Italy and start a vineyard.
    Quit my job & volunteer in Alaska for a year (I’ve always wanted to live there)
    Give my parents money for all the times they have paid for things for me.
    Pay for my brother’s college education
    Start a non-profit company that is all about DOGS!
    Fake Boobs (yes, I just went there)
    Invest a lot of it so I wouldn’t piss it all away and while it’s accruing interest, be a high school teacher once and for all.

  13. Rebecca_C says:

    I think you need to dream bigger. With $330mil you could get THREE condos.

    Also, what the hell is a “whammie” exactly? I found myself shouting it all weekend whilst in Vegas and have no idea why…

  14. I actually have a fear about winning the lottery lol.. I know I sound like a weirdo but I wouldn’t mind a couple million but I’m scared of the really big ones like 250 million – its a combination of LOST and The E! True Hollywood story I watched on it hahah… but reagardless, I do still think about what I’d do with all that money and I’d probably travel a whole lot and have houses all over the place. :)

  15. Jenn says:

    winning the lottery is one of the best things to dream about – hands down. i dream of a very luxurious life (clearly not in milwaukee) including lavish vacations, a home in the moutains AND on the beach, a personal chef, personal trainer, becoming best friends with marc jacobs (because money can buy that, right?) and daily hair appointments. i should really stop thinking about this now before i curl up in a ball of depression. :)

  16. Janalee says:

    this subject has come up once or twice in conversation with friends but I think the funniest response was to apply for jobs and then purposely mess up the interview.

  17. Kara says:

    My husband works with the lottery on IT projects so I’m not even eligible to play. And even though I hardly even actually bought a ticket, I was really bummed when he told me that we were ineligible. No one even asked me!

  18. Abby says:

    Pay off student loans – that’s all I want to do. I just want to win enough to pay them off, the rest is just gravy.

  19. Angela says:

    Why not get a sexy cleaning MAN?!?

  20. Last week, in charlotte, we had a $260+ million jackpot and I bought a ticket, just for the heckofit.

    and, I also ended up daydreaming about what I would do with my winnings that I actually convinced myself that I was going to win. Yeah, what a bummer it was to realize that some dude in SC won MY MONEY.

  21. I would do A LOT of traveling, buy gifts for family and friends, buy another dog, and open up my own non-profit…and go back to school!

  22. Daisy says:

    Brilliant! Love the dog training one – I would so buy a little army of schnauzers and each one a little chalet kennel to live in. Also Chanel stuff!

  23. Andhari says:

    Ohhh to win that much money, sounds like a dream. Ill move to Europe and live there probably with that kind of money, score myself a fabulous pent house in Paris..buy an aston martin..travel every time I want..start my own lines of clothing and hiring amazing designers..make a movie starring myself and a hot actor hahahhaa..produce my own album and hire timbo and kanye west to help me out..

    sigh..day dreaming makes me go nuts..

  24. Baby says:

    Buy my very own island & build a sick beach house for me and my love (who I will find when I win the lottery, obviously) to spend our days laying on the beach, surfing & playing with the dogs/kids (whenever those happen) and fly out only those who I REALLY want to see to come stay with me whenever they’d like.

    and then I woke up…HA!

  25. I don’t play the lottery but man, I sure do like to fantasize about what I’d do with ALL THAT MONEY.

    Lifetime supply of cheese & wine? YES PLEASE.

  26. hahaha, yessssssssssss. excellent edit. now when you win i’ll have proof…..


  27. YOU FORGOT ABOUT ME!!!!! : )