I was recently at the supermarket with my wife when an announcement came over the PA noting the Powerball Jackpot had reached 1 billion dollars.  We bought a couple of tickets and, on the way home, discussed what we would do with the money if we won.  

     There probably isn’t anyone alive who hasn’t dreamed of winning the lottery.  I’m sure this includes many people who have never even bought a ticket!  It’s fun to imagine what you would do with all that money.  I’m not talking a few hundred thousand dollars.  I’m talking about the big one—hundreds of millions of dollars—life-altering money for you and your family, potentially for generations.

     While I don’t believe I’ll ever win the lottery, I think it is a fascinating financial topic.  However, I’m not going to talk about the astronomical odds against winning or the poor financial decisions of lottery winners.  It’s too easy to write about the relative benefits of lump sum vs annuity-type payment options.  I won’t even discuss taxes, which is one of my favorite subjects!  Today, I want everyone to dream about what they would do with their lottery winnings and then reflect on what that says about you and your relationship with money.

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Changing Values

     I have been aware of the lottery since I was a child.  My father played regularly, and I remember him manually picking numbers by filling in the circles on the ticket scantron style.  I would ride my bike to the store to buy him cigarettes and lottery tickets (life was different back then).  I watched on TV as the ping pong balls came down a clear vacuum tube, and the Vanna White-like hostess would grab them and turn them over to reveal the winning numbers.   

     The way the lottery is played, and my dreams have changed a little over the years.    


In my youth and young adulthood, I fantasized about buying a mansion, sports cars, and traveling the world.  Becoming super rich overnight seemed like a great thing—endless fun and endless money.    

     It didn’t go much deeper than that because I wasn’t much deeper than that.  I’d never had any real money or know anyone else who did.  My understanding of money was that it was just for buying fun things and experiences. 

Residency/Early Career

     I drove about 90 minutes in residency to moonlight at a small-town ER.  On the way was a huge house in the country with at least two Ford GTs (the early 2000s version) and a few big trucks on the property.  The rumor was that the family were lottery winners.  

     What would I do if I were so lucky?  I still dreamed of material things: a nice house, maybe a vacation home, traveling, and my own Ford GT.  But I also began thinking about philanthropy, helping family members and charitable organizations.  Finally, I thought about what it would mean for my career in emergency medicine.  I would be fine without earning money, and I would be afraid of the liability that working would bring.  But I also wouldn’t want to have spent all the time studying and training and never put it into practice.  So, I puzzlingly dreamed of working for free in an inner-city ER while living in my mansion.  I’m not sure where I thought I would park the Ford GT at the hospital, though.    


     During the middle part of my career, I paradoxically became less interested in material things but obsessed with money and investing.   My day-to-day was focused on working and building my businesses.  My lottery dreams changed from buying mansions and cars to building a business empire.  I dreamed of quitting my job in the ER to focus full-time on business and investing my lottery winnings so that I would be even richer when I was old.  In fairness, I did plan to give a lot of money away to charity.  I even researched enough to discover that you can’t donate all your lottery winnings to charity to avoid taxes due to the limit on charitable gift deductions.  (Sorry, I had to sneak some tax information in here somewhere).  


     And this brings me back to my recent conversation in the car with my wife.  She said she would want to move to a new home if we won, which was no surprise to me.  We have looked at houses on and off for the last few years, but ultimately, I don’t want to move.   We agreed that we would keep our current cars.  We bought two new Hondas last year and are both happy with our choices.  I couldn’t think of anything else that I wanted to buy that I didn’t already have.  My wife wanted to travel more.  That’s it.   I would like to give most of the money to charity and have my children involved in that process.       

     We can already afford to live in a more expensive home and drive more luxurious cars, but we choose not to.  No matter how much money we won, that would stay the same.  My wife wants to move closer to our children’s school, not because she is unhappy with our current home.  We have the option to live anywhere we want, but we currently wish to stay in Austin.  

     I disagreed with my wife about traveling.  With our children in school, we don’t have time to travel more than we do (which is a lot), and I didn’t understand how winning the lottery would change that.  She believes that if money were truly no object, we could visit her family more in Brazil and perhaps take more weekend trips.  It would be a lot easier to go to Brazil for a week if the children were in first-class seats that fully reclined, and they got some decent sleep on the flight.  We could also fly private within the U.S. for weekend getaways.  As per usual, I lost the argument.  

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Lottery Lessons

     The casual conversation with my wife struck me as profound precisely because of what I don’t want.  I don’t want a mansion anymore.  Maintaining a huge house requires a full-time staff, which seems like another job.  I also like to feel close to my family.  I don’t want to have to search a 10,000 square foot house just to find my kids.  I’m happy with our vacation home, but certainly don’t want another.  I’ve already decided that I don’t want to quit working.  There is nothing that I want that a lottery win could buy.  I’m happy and content with my life right now.  Isn’t that the point of having money in the first place?  

     However, I did listen to what my wife had to say.  I already knew about her desire for a new home.  We simply disagree about the relative utility a new home would provide our family.  I wasn’t aware that she wanted to travel more, though.  After reading (and reviewing) the book Die With Zero, I have been looking for ways to spend money that would bring value to our family.  If my wife would want to travel more if we won the lottery, why not try to do it now?  Within a few days of our conversation, she had a weekend trip booked to Los Angeles to see a friend later this month.  

     I also considered my dreams of giving more money to charity.  Why wait until you win the lottery to be generous?  I already have a charitable giving goal and plan, which I will write about at some point.  However, this exercise reinforced my desire to be charitable and to find a way to involve my children in that process.  


     I encourage everyone to take some time and dream of what you would do if you won the lottery.  Instead of looking at it as a fantasy, analyze what it means and try to make a version of it happen now.  If you are financially independent and find yourself dreaming of material things or experiences, are you living a life of deprivation?  Perhaps you should spend a little more money to live the life you want now.  

     Conversely, if money is holding you back from your dreams, it is time to make a change.  You don’t have to win the lottery; you need to become financially independent.  A great place to start on your path to FI is the Financial Vitals Checklist here at Business is the Best Medicine.  Take control of your finances and turn your life into a lottery winner’s dream.   

     What are your lottery dreams?  How have they changed over time?  Leave your answers in the comments below.  Subscribe to Business is the Best Medicine so you do not miss any upcoming posts.  Thanks for reading.