Life, Money

You Just Won $55 Million! Now What?

I was going to publish a post about my on-going rental property insurance claim, the unit with the flooded basement, but I needed a break from anything related to rentals today, so I decided to post something a little more entertaining. You Just Won $55 Million! Now, What?

I stopped at the gas station on my way home and noticed the billboard advertising the latest Lotto Max jackpot. “The next jackpot is Friday : $55,000,000”. I rarely buy lottery tickets, I always feel like I am “winning” $2 /week that way. But, once in a while, when the jackpot is really high and I happen to be at the gas station or grocery store, I do buy one, like I did today.

When I got home, I told my kids “I bought the winning ticket! I can quit my job on Monday and travel the world”. We all smiled at each other , crazy mother speaking, we all know I won’t win. But what if I did?

What Would I Do If I Won $55 Million?

(We will assume after tax for our US readers, we don’t pay any taxes on lottery winnings in Canada)

My first thought is that it would be too much money to win at once. I have read so many articles over the years about big lottery winners and how many of them go bankrupt within the first few years. Check out Here’s why lottery winners go broke. What would I do with all that money? I am frugal by nature and I don’t think having millions would make me a much different person (but I am willing to try if anybody wants to share). I would also be worried about everybody else’s expectation if I won that much, all the new “friends” I would attract, the “forgotten” ones, all the extra stress!

The Breakdown

But then I started thinking of a few things I may consider spending money on. So here is my best guess at what I may consider doing, assuming I won $55 Million and have to spend/invest it ALL. (And DON’T JUDGE, it is a lot of money to spend!:)


Lottery breakdown

What’s Behind The Numbers

  1. Invest $4M in a GIC (Guaranteed Investment Certificate) or bond ETF to secure some income and $6M in dividend paying ETF and stocks. Assuming it would generate a minimum of $300,000 dividends/interest per year. I may have to re-invest some of it!
  2. Set a trust for my kids with $2M each and invest it in GIC or bond fund. Assuming a 2.5% return, it would generate $50,000/year. Hoping it would still keep them motivated to want more and work for it! You hear so many stories about kids losing any kind of motivation when they get too much money too soon.
  3. Give $1M each to my sister and brothers and $200K to each of my close relatives (the ones I like).
  4. Pay off my two best friends’ mortgages (estimates) and give them $500,000 cash. Sorry ,no! you can’t be my best friend too!
  5. Sell two of my rental properties and potentially give the third one to the current tenant. They are good people and will probably never be able to afford a house.
  6. Give to charities (Cancer research, Mental illness, Human Society, Doctors without Borders and a few others) or maybe create my own foundation so I know where the money is really going.
  7. Hire a full-time personal chef to cook amazing delicious meals when I don’t feel like it (or I just feel like eating a delicious meal!). I am thinking for at least 10 years, I may get tired of it afterwards. Assuming $150,000/year for 10 years but I may go for a part-time chef for 20 years instead! (Decisions, decisions) Or I may look for a much cheaper chef and have more fun money (#10)! (Who am I kidding, I will just invest the difference).
  8. Rent a private jet so I never have to waste time at an airport again. Go anywhere I want, anytime. My first thought was to buy a jet but the maintenance and upkeep would probably be a real pain plus it costs a lot of money. I could buy my own 2013 Dassault falcon for $19M!!! Check out this site if you are in the market . Considering I don’t want to fly all the time, renting makes more sense. I could travel 4 times a year for the next 25 years at an average of $150,000/trip depending on the jet and distance! Some years less some years more!
  9. Rent properties all year round in different countries, a few weeks at a time, most of them with beautiful beaches and in warm places. Average 120 days/year @ $2,000 a night for 25 years.
  10. Keep $200K cash just for fun!:)

But would I really do all this? Would I spend $150,000 just to get anywhere quickly and conveniently when I could spend less on business class tickets to get to the same place (I guess with $55 million you may give up economy)? Am I too frugal to win $55 Million? Could I justify my spending because I would have so much to spare? I mean $15 Million over 25 years for a private jet!!! But pretty cool! And would I really write a check to charity for $10 Million or am I just saying that to make myself look feel good knowing I will never have that kind of money? So many questions, I guess there is only one way I will ever find out!

I read that $800 million a year of prizes go unclaimed!!!  Maybe I will go after the unclaimed prizes instead.

How about you, what would you do with $55 million dollars?  Not whether you would quit your job or not but, what is your best guess at how you would spend/invest  it ALL?

Check out a few interesting articles on lottery winners:

Here’s what 11 regular people did with their money when they won the lottery

Here’s who won the 5 biggest US lottery prizes ever

And another entertaining post from Dads Dollars Debts on winning the lottery

I won the lottery! Holy $$$$

37 thoughts on “You Just Won $55 Million! Now What?

  1. I love Canada. Even for the lottery winning, you don’t need to pay any tax. How nice! If I won the $55M, I would claim the prize anonymously, live like an average gal, and keep smiling privately. I hope you win this time, Caroline. Good luck!

    1. Property in Hawaii sounds pretty good, several islands to choose from? With that much money invested, no worries for the rest of your life, your kids’ life…good plan too:)

  2. Cool post, Caroline! Planning how you would spend lottery winnings is always an interesting thought experiment. Similar to you, I mostly avoid buying lottery tickets. But I’ll buy the odd time when something or someone reminds me. Perhaps this post is my reminder….If I ever won, deciding how to allocate it would be the most fun part. I’d invest a lot of it, I’d definitely give to family, I’d give a sizeable chunk to charities, I’d travel a lot, I’d buy a house (nothing super extravagant), and I’d probably buy a Tesla. Otherwise, I wouldn’t be that much different. I’d still focus on blogging and investing and I’d want to maintain the same lifestyle. But it would be hard to stay the same lol. I’d have to find a new challenge to fill the void of financial independence. Probably giving and helping others.

    1. I agree Graham, it would probably be hard to stay the same no matter how hard you try. I would definitely keep “working” whatever it is. Maybe I could be an investor on Shark Tank!!!

  3. Well this is just irresistible. Here’s me:
    1. I’d give away $10M just like you did.
    2. I’d spend about $300k on my house – I don’t need bigger or anything but all the projects we’ve ever dreamed of would happen right now.
    3. I’d set aside $1M total for college for my three kids. That should cover it.
    4. I’d set aside $2M total for each of my kids to have a nice house as a wedding gift. I would probably not tell them about this.
    5. With $10M I’d purchase a bunch of land and build a nice but not crazy retreat center on it so that any time I want to get together with a big group we’ve got a kickin’ place to do that. I can buy 5k acres of mountain land with hunting, farming, skiing and fishing opportunities for about $6M, plus another $4M in improvements to make structure, roads, etc. This would be within an hour drive of my house.
    6. I’d probably buy a pickup truck… but not a fancy one. Call it $25k.
    7. With the remaining $20M or so, I’m going to spend my time investing in small business stuff in Utah, writing and learning to do all that stuff at my retreat center (like hunt and farm).

  4. Here’s what’s interesting to me…you would invest all your money in funds and NONE IN REAL ESTATE. And, in fact, you would sell and give away your current rental properties. And then, you would buy no more real estate, instead renting vacation homes around the world….Hmmm, if I was a wise person, I would think you don’t like real estate investing???? Oh my, hahhaahha

  5. I would spend a few months a year in Mexico, and quit my job for sure. Funny…no specific purchases I can think of. I would give a lot to friends and charity like you.

  6. Hi Caroline
    Fun post, it is always nice to dream. I would be similar as you with the winnings but the majority would be invested in stocks. I hope you win !!

  7. I had no idea Canada didn’t tax lottery winnings. Apparently that’s the place to play 😉 Honestly though, I think $50k a year per kid is WAY too much. I have a hard time with money trusts for kids in general because it’s a serious incentive not to work before you’ve even gotten started. More than paying for most? all? of college and paying to have them join you on vacations seems more than fair to me.

    1. I agree Angela, that’s a tough one with the kids. You want to be generous but you don’t want to spoil them either. My kids are hard working right now, maybe that would just ruin them! I may never know.

  8. I would invest it. 80% in S&P 500 index fund and 20% in Short-term bond index (Buffet style). That should earn $952,600.00 in yearly dividends and interest. Should be sufficient to fund education for lots of kids.

  9. The no tax part is definitely awesome.

    I guess my chances of winning would be 0 because I don’t even buy the lottery. I have something against the lottery but my parents buy it ALL the time! They think it’s the only way for them to get rich… sigh lol

    If I won, I’d invest most of it and donate it. I want that money to keep growing forever.

    On the side, I’d save some for myself to invest in stocks and likely a business I have a passion for. I’d also give to close family members who were there for me. We would splurge on a few luxuries and just live like regular ppl while running that business haha. If the business becomes successful, it would be nice to donate some more 😊

    1. You made such a great point about most people who buy lottery tickets, they think it’s the only way for them to get rich! Even if the odds are very small.
      Invest in a business sounds great:)

  10. I didn’t know that you don’t pay taxes on lottery winnings here!!

    Since they tax us to the nines on everything else maybe they should tax lottery winnings so we can pay a little less tax 😉

  11. This is fun 🙂

    In all likelihood I’d invest $20m for me to live off, and make plans to do good with the rest. I’d be thinking trusts to support family, and a seriously cool philanthropic effort with the remaining $35m, all on causes that matter to me.

    1. It was really fun to come up with the list. I have been day dreaming about private jet and chef since!!! Philanthropic effort with $35M should keep you busy for a while, that is a lot of money to donate:)

  12. We’re a group of 20 at work playing the lotto max this Friday. If we win and split between 20 people, we would walk away with 2.7 million each. I think I would invest everything at 4% dividend yield and just quit my job to pursue my passion 🙂 The return alone would double my current paycheck 🙂

  13. Hey that was a fun post to read! I would keep around $25 million and invest the rest. Buying a couple of rental properties, fund my son’s college savings account, distribute to close family members, and donating to different charities are what I want to use the money for.
    I like your idea of renting a private jet, beats the hassle of going through the long lines at the airport. Might do that too!!

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