Why Buying Powerball Tickets Is A Great Way to Evaluate Your Life

by | Aug 11, 2020

This is a Powerball Ticket I contributed to my Lottery Trust in 2018. (It didn’t win)

I buy a Powerball ticket 4-6 times a year and have been doing so for about 20 years. For me, buying Powerball tickets has led to some powerful benefits.

First, let’s get this out of the way: I don’t expect to win. The odds in winning the Powerball jackpot are 1 in 292,201,338. To put that in perspective, there are about 210 million people in the U.S. over the age of 18. So, if everyone in the U.S. who could legally buy a Powerball ticket bought one on the same day, the odds are that maybe one person would win.

Important Questions

When I buy a Powerball ticket I set aside a bit of time to imagine having that much money and I ask myself what changes I would make in my life if money wasn’t an issue. Questions like:

  • How would I want my job/career to change?
  • Would I go back to school to get another degree? If so, in what?
  • Would I move to another city?
  • Where would I want to travel?
  • What would I want to support charitably?
  • Who would I want to share it with?

I have found pondering these questions about what would change in my life if money wasn’t an issue tells me a lot about the current state of my life. In reality, none of the above questions are really dependent on having hundreds of millions of dollars. If I were to be unhappy with my job/career (I’m not), there is a lot I could do to change things even without winning the lottery. Same for the other questions. If I don’t like the city in which I live I could move. If there is somewhere I really want to travel to I can save and go there. I can support charities that I think are important on a more modest basis and/or contribute my time. Answering the question about who I’d share the winnings with tells me a lot about what relationships are most important to me and to keep investing in them. In reality, there are many changes we can make in our lives that aren’t dependent on money. Sure, having great wealth can make these changes a lot easier, but we have control over more things than we think we do.

Another question that I ask is what my life’s purpose would be if money were not an issue. If the desire to make more money is off the table what should I pursue? Thinking this way makes me realize that the quest to make more money is a distraction. It’s easy to get caught on the hedonistic treadmill. As I result of pondering winning the lottery I spent time and effort figuring out my life’s purpose and it’s not dependent on having a lot of money.

A Few Other Powerball Things

Only Buy One: I only buy one Powerball ticket at a time. Why? One ticket is enough for the insight and entertainment of the questions I lay out above. Buying more than one doesn’t lead to any additional insight and doesn’t change my odds of winning materially. Buying one ticket is 1 in 292,201,338, or 0.00000034%. Buying two tickets is 0.00000068%. Buying 10 tickets is 0.0000034%. These are all very close to zero. You’d have to buy 2.9 million tickets to have a 1% chance of winning.

Lottery Trust: In 2000 I created a lottery trust called the Engender Trust (“engender” was the dictionary.com word of the day on the day that I created the trust). It is an irrevocable trust that is outside my estate and which has the descendants of my great-grandparents and my wife’s great-grandparents as beneficiaries, including my wife and children. I am also a discretionary beneficiary (the trust is arguably still outside my estate because I structured it as a self-settled spendthrift trust). My wife is Distribution Trustee and I’m Investment Trustee. When I buy a Powerball ticket, I take a picture of it and email my wife and say “I hereby contribute this Powerball ticket to the Engender Trust.” What this means is that the gift to the trust is the value of the ticket (i.e. $2), and if the ticket is a winner then the increase in value from $2 to hundreds of millions occurs outside my estate. Pretty cool – all that money can be distributed out to the beneficiaries without gift tax and there will be no estate tax as it passes through the generations. It would probably be challenged by the IRS which would also be cool. Note that this doesn’t help with the income taxes due on the winnings.

Investment Musings: I also think about how I’d invest the Powerball winnings. This sort of musing is a nice check on how we advise our clients to invest. I’d invest mostly passively (a combination of indexed accounts and factor-based passive) and then some private investments such as private equity, venture capital, and private real estate. I’d also invest in alignment with my values, including private investing in companies who are trying to make a positive difference in the world. I’d also have enough in high-quality muni bonds to stay disciplined in down markets. I’d try not to look at the portfolio often – maybe just once or twice a year. Looking at investments a lot leads to tinkering which is almost always a bad idea.

Charitable Giving. I think I’d be most excited to create a huge private foundation and give to charitable causes that will make a difference for people and the planet.

I Don’t Want to Win: One thing I’ve realized as I’ve mused about winning Powerball is that I don’t actually want to win. I know that most people’s lives take turns for the worse after winning the lottery. While I think I’m better suited to winning than the average person given what I do for a living (i.e. a wealth advisor to ultra-high net worth families), I also realize that I should respect base rate probability that winning the lottery will make things worse. Things are really good in my life right now. I suspect that winning Powerball would lead to decisions that would negatively affect my happiness. UPDATE on 8/29/23: I am wrong about this. Winning the lottery doesn’t ruin the winners lives. Rather, lottery winners tend to report greater life satisfaction. Check out my Forbes article on this topic: Debunking The Myth: The Surprising Truth About Lottery Winners And Life Satisfaction

Be Careful About Buying Them with Co-Workers: Ten plus years ago when Powerball was at a record-high jackpot (over $500 million), about 20 of us decided to pool some money and buy some tickets with the agreement that if we won we’d split it. After we bought the tickets I realize that this was a HORRIBLE IDEA from the company’s perspective. What would happen if 20 of us all the sudden had millions of dollars? What if half or quit? We’d have a big hole in our personnel that would be tough to fill. And at the time, we’d only had about 30 employees.


  1. Interesting exercise. I will journal and (maybe) send some of it to you if I end up doing it! ;). Or at least let you know my top couple insights…

  2. So long as a government agency is retaining a percentage of total ticket purchases (in addition to admin costs, etc) winnings paid out will always be less than dollars taken in. Therefore, if one person theoretically bought all of the tickets, he/she is guaranteed to lose. In a way, buying single ticket offers the best chance of winning!

  3. This is good fun in terms of a topic, but really great thinking and writing. Another reason why the ifod is secretly your purpose !

  4. Great and interesting article – enjoyed reading it! I’d like to say that do the same or very similar things as well, only I do it without buying a lottery ticket;-)!

  5. Thanks John! I do the same thing when I buy the lottery ticket. It is a fun reflection. Matt

  6. You write: “Most people … seem surprised … when I tell them that I buy them …”

    You wanna surprise people?

    I buy them, and never check them and, after the pile gets old enough, I shred them.

    Why? It is bad choice to waste your money, but it is a real sin to waste your time.

    Lottery tickets are transient pleasures, much like a movie or a cigarette or a beer or a visit to The Louvre or The Met. I buy the ticket, and I get to walk around thinking that I might have tens of millions of dollars in my pocket. That’s a lot of bang for my buck.

    But checking lottery tickets is a waste of time that turns having bought that ticket into a waste of money. It is a largely pointless, grinding, discouraging, self-desecrating chore best avoided.

    When my adult son learned about this, he objected violently. Okay, said I, I will give you a pile of lottery tickets, and you check them, and you pay me just ten percent of your winnings. Reacting as if I had offered him tissues that I had blown my nose in just once, he refused the offer.

    Buy them, age them, shred them … that’s the ticket, lad.

    • Great point!
      I rarely check them either – the odds are too low and I figure if there was a local jackpot it would be in the news.
      Love your interaction with your son!

  7. Fascinating to ponder, and a good exercise on a regular basis. Thank you!

  8. I love that you’ve written about this! I rarely play but whenever we do, I say to Scott “the first call is to John at STL Trust. He’ll know what to do!”



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