First 10 Things I’d Do if I Won the Lottery

With the lottery topping out over a billion dollars recently, the “what would you do if you won the lottery” discussion has been at an all-time high at the day job this week. Therefore I will start this new list experiment with the extremely unoriginal topic of what would I do if I won the lottery.

I should start with the caveat that I don’t actually play the lottery.

The lottery is a self-imposed tax designed to move the tax burden from the wealthy to the poor and uneducated.

I will throw a couple bucks into the lottery pool at work because if those guys somehow win, I don’t want to be the only person that has to show up for work on Monday.

Here are the First Ten Things I’d Do if I Won the Lottery:

1. I wouldn’t tell anybody.

For at least the first two days I wouldn’t tell anybody. Not a single soul. Okay, I’d tell Naima. She is pretty good at keeping secrets. Then I’d start setting a plan in motion.

2. Hire a lawyer, financial adviser, and a personal assistant.

I don’t know any lawyers or financial advisers like the kind I would need. I would start quietly interviewing lawyers and financial advisers without them knowing it. If they treated me well without knowing I was filthy rich, then they would have a chance at being hired. I don’t need anybody that is nice to me to be nice to my money.  That is essentially the downside to suddenly becoming wealthy. I’m the type of person that would never trust a new person coming into my life at that point.  At least not 100%.

As for the personal assistant. I’d be done answering my phone. I wouldn’t be able to handle all the people that  would be coming out of the woodwork to get at me. I’d need a buffer between me and the rest of the world.

I have a few friends that I know hate their job. A few of them might make great personal assistants. I’d start with who I think would be the best at it. If they weren’t interested, I’d go to the next person. Whomever got this job would need to be a friend first and then they’d have to work very hard. This job isn’t a handout. My text messages are known for their quality. No slippage would be allowed.

3. Tell friends and family.

Not all my friends and family, but the inner circle. Or to completely (and shamelessly) steal a phrase from a friend: I’d tell the ones that have the key to Monicaville. I do know exactly who is on this list. That is one of the quirks of living the life I’ve lived.

After telling this small group of people, then I’d be ready to turn the ticket in and collect my winnings.

4. Have the best lotto winner’s press conference ever.

I’m going to let the people that are going to come out of the woodwork looking for money, not to bother. Boone Booster Club. Yeah, I’m not buying you a new football stadium. You have enough money. What’s left of Boone’s Music Department, you can expect a big check. University of Iowa, don’t bother calling. Iowa State University. There is a check coming your way.

5. Pay off debts of immediate family.

I don’t care if they owe $100,000 or $10. If you are in my immediate family, you no longer have any debts.

The question you might want to ask is this: How do I define immediate family?

I won’t tell you now, but there will be a day when I write about this subject and the people who taught me what family means and how that word is properly defined.

I’d also pay off my debts as well.

6. Give max tax free gift to friends.

If you didn’t learn about my winning the lottery at my awesome press conference, then I’d be giving you the maximum amount of cash that I can give you without you having to pay taxes.

There are no strings attached. You want to use that money to buy hookers and blow. Whatever, floats your boat. If you want to use that money to buy Nebraska season football tickets, you aren’t getting any money next year.

7. Buy block across the street from my church.

“My” church is fairly landlocked right now. However, there are several crumbling buildings across the street from it. We actually own one of those buildings and when what happens to that ruin gets decided I expect their to be lots of fireworks.

So I’d just take this controversial topic off the docket of all future church meetings.

I’d buy all the buildings across the street. Tear them down and build a new building with a full-sized basketball court. A real basketball court. None of that carpet on the floor of the court garbage (I’m looking at you Open Bible). The rest of the building I’d let somebody else design, but it would be designed as a place for youth activities and any other program the church wanted to run.

I’d also be righting large checks to the American Diabetes Association and the American Cancer Society. Crawford Hall would probably get a decent check at this time.

8. Invest in the businesses of friends.

I’m probably not going to throw a ton of money their way, but for my friends that run their own business I’d throw a little Angel Investment their way. I would possibly consider helping a couple of friends who are amazing cooks open restaurants if that is something they would like to do.

If that is what it takes to get Scottie D.’s pulled pork pizza, then that is what I’ll do.

9. Call Jamie Pollard.

I’d  want the same football seats. I don’t really like sitting with rich people because it has been my experience that rich people don’t really like me. Something about being able to form my own opinions rather than cow-tow to their opinions.

However, I’m going to need good seats for men’s and women’s basketball. I don’t need my name on any buildings, but he could put my Mom’s name on the training table.

I’d also like to see what kind of donation it would take to consider getting rid of the terrible I State logo and going back to something cool. Walking Cy!

10. Quit my job.

I’d give my current employer 2 weeks notice.  I’d want to be paid for all the PTO I’ve banked. Yeah it is a drop in the bucket compared to the 800 million I have in the bank, but I earned that money. I value that more than money I won. After all, one of the greatest evils in this country is unearned (inherited) wealth. I’m not that guy. If I ended up broke so be it.

I often here people say that if they won the lottery they wouldn’t quit their job because they wouldn’t want to lose their health insurance.  If I’m starting with $800 million in the bank, I think I can afford my own health insurance.

Plus I can tell that my dog misses me during the day. She’d be super pumped.

Sure I’d miss a few of my co-workers. That is why I would take the ones I like on an all-expenses paid vacation once a year. I’m sure they’d be fine with closing down the Network Engineering Department once a year. Right?


I think that about covers my first 10 actions if I’d won the most recent lottery. Now the next 10 things I’d do… Some other time.

Next week’s list will either be my 10 favorite Photography 139 images or I’ll rank the Rocky movies from worst to best or something else.

9 thoughts on “First 10 Things I’d Do if I Won the Lottery”

  1. They asked this as an icebreaker question at a class I attended in Wisconsin the last few days.

    I went with swimming through it Scrooge McDuck-style (provided they were new bills/coins). It wouldn’t actually cost any money, which I could invest/donate/plan later – but it would be satisfying.

  2. It is such a generic topic that I hate to even broach it, but I figured it was an easy first topic.

    You know. I doubt that you could physically swim through it. Not you personally, but anybody. That would be a good thing for MYTH BUSTERS to tackle.

    I think you could lay on money. You could even do a money angel. But there is no way a person could swim through money.

  3. Yeah, definitely not if it were coins, for sure. But ducks are advanced swimmers, and their bodies are aerodynamic, so maybe they have a leg up on us.

  4. Ducks are fascinating creatures. Also, they aren’t dicks like their cousin the goose or as they are called in Minnesota, grey ducks.

    Maybe the coins are coated in something that pushes them away from each other. That would probably require magic.

  5. Geese really are dicks. (I won’t say “grey ducks.”) We went to Red Robin or something like that on a trip to Jordan Creek a couple of summers ago (so far I hate every part of that sentence), and there was a goose who had built a nest on a trash can outside of the restaurant. I took Alice around it the long way, but it tried to attack Jon just for parking our car. They’re just a-holes.

  6. That does sound like a pretty horrible day. But I have an unhealthy disdain for malls.

    But Red Robin serves pretty tasty burgers for a corporate restaurant.

    In that scenario it was protecting its nest. I’ve seen pregnant women act in a similar manner. But the best part about geese is that while they are dicks, they can do nothing to you. They can bite you all day and all it does is tickle.

    The A-Hole thing reminds me that in Manhattan there is a big concrete Manhattan on the side of a bluff there. Apparently one of the cool things to do in that town is have your picture take in the “A hole” of that sign.


  7. I don’t blame the goose, for sure – but it was definitely aggressive. The burger was easily the best part of that day.

    I’m laughing at the A-hole thing. Not because it’s clever, but because it’s so terrible. I’m picturing people sitting in the “a hole” with a thumbs up and posting it all over the internet.

  8. I never thought about the empty spot of a letter as a “hole”, so when Laura told me this at first, I didn’t understand.

    Then I asked, but there are 2 “A”s in Manhattan. Which is the right one?

    “It doesn’t matter”

    But on my next trip to Manhattan, I will have to do that. I visited the Manhattan Hill solo, so I could not pull it off myself.

    Almost more fascinating was the KS Hill across the river. You definitely visit that at your own risk.

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