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15 Life Lessons from the Game of Monopoly

Updated on December 5, 2012
Monopoly, a game full of life lessons
Monopoly, a game full of life lessons

Deep meaning lies often in childish play.

–Johann Friedrich von Schiller (1759-1805)

I have learned a great deal about life from Monopoly, a board game created during the Great Depression for dreamers, schemers, aspiring real estate moguls, and other assorted capitalists. An estimated 1 billion people in 111 countries have played this game since 1935, and I still play it occasionally though not with as much gusto as I used to play it.

This looks like my average stack of bills.
This looks like my average stack of bills.

Modern electronic Monopoly

The problem is the electronic version of Monopoly, which comes with debit cards and a computerized bank. Playing this version leaves me feeling hollow. It is too abstract and far too much like real life where my bank account disappears one swipe at a time. Swiping a debit card is not the same as holding paper money. Checking the balance with another swipe is not the same as counting each bill. A cold plastic card is not the same as feeling “real,” colorful money in your hand. Before the existence of the electronic bank, you could look at your stack of bills and know whether you were okay or whether you were in trouble. Now you have to check your balance, and the “bank” has already added it up for you. I miss the sheer joy of trading in ten twenties, five fifties, nine five’s and five one’s for a crisp, golden $500 bill. There were no decimal places, no strange noises, and no beeps in the old days, just the feel of cold, hard cash. I miss those days—in real life, too—but I’ll never forget those lessons.

I learned more about life playing Monopoly than I learned playing any other game.

The thimble always beat me.
The thimble always beat me.

15 life lessons

Everything on the Monopoly board has its place. Community Chest goes here. Chance goes here. We all begin our journey here. We go in a clockwise direction. We roll the dice in the middle. We take turns. We follow the rules. If we are unsure, we consult the rules. You keep your money and deeds on your side, and I’ll keep my money and deeds on my side. Someone always wins, and the rest of the players lose.

1. In life, order--even order that ends in defeat--is better than chaos.

As a child, I chose my token at the beginning of the game carefully. If I wanted to take the game by storm, I chose “fast” tokens like the shoe, the Scottie dog, the race car, or the horse and rider. If I was planning a more considered approach, I chose the wheelbarrow. I didn’t choose the wheelbarrow that often. When I was out for blood, I chose the battleship or the Howitzer cannon. No matter what I chose, however, I usually lost to the thimble, which was used exclusively by my mother.

2. In life, good luck charms aren't lucky--you make your own luck.

The highest roll goes first. The lowest roll goes last. Sometimes it’s good to be first. You get first crack at the first row of properties. Sometimes it’s not as good to be first. You might land on the tax space, lose $150, and fall immediately into last place. Sometimes it’s best to be somewhere in between. And no matter who goes first or last, the order of play doesn’t usually determine who wins in the end.

3. In life, how you start isn’t always how you will finish.

Why did everyone have the same salary? Just wondering.
Why did everyone have the same salary? Just wondering.

If you draw a Community Chest or Chance card, you might get good news or bad news. Sometimes you win $15 for second prize in a beauty contest, and sometimes you win an election and have to pay everyone $50. You might land three consecutive times on other players’ properties, but then a Chance card sends you to Go to recoup your losses. You land on a light blue space with a hotel and lose a bundle. Another player lands on an orange space with your hotel and you make the money back and then some.

4. In life, it often evens out in the end.

Rich people have tuxedos, ties, tails, top hats, canes, and bushy moustaches. They also smoke cigars and carry around moneybags marked with dollar signs. They even get to prop their legs up on desks while at “work.”

5. In life, some people have it hard, and some people have it easy.

When you go directly to jail, you lose your top hat and get new striped clothes. Police kick you on your way to jail. If you pay your fine, they let you out. If you are low on funds, however, it’s sometimes best to stay in jail for a few turns, especially when the board is full of other players’ hotels. You can actually make money in jail by collecting rent, and if you gamble and roll doubles, you can get out of jail without paying the fine.

6. In life, sometimes crime pays, but for the part, crime doesn’t pay.

Easily the space I landed on most while playing--unless an opponent had a hotel on Boardwalk
Easily the space I landed on most while playing--unless an opponent had a hotel on Boardwalk

Utility bills fluctuated from turn to turn. Sometimes they were high, and sometimes they were low. If an opponent had a matching set, the rent rose. The more houses and hotels you had, the higher your repair bills.

7. In life, bills are often random, and rent can change at a moment’s notice.

At first, I didn’t care what “10%” meant on the income tax space. But when I started "doing" my own taxes during the game, I learned that I could often save a few dollars instead of paying a flat rate of $200. I learned to hate the luxury tax and that diamond ring. I didn’t want to land on that space. I wanted to land on Boardwalk or Park Place. That space, however, did teach me that diamond rings were expensive. I’ve bought a few of those. I’m glad the wearer of the last one still wears hers.

8. In life, taxes are a pain the bank account, but it's best to do your own.

I often mortgaged property to pay a bill or purchase houses for properties elsewhere. Mortgaging property was a great way to pad my bank account, but if I wanted to rescue a property from mortgage, I had to pay the bank interest. I didn’t like paying interest to the bank. I bought the property outright, didn’t I? I didn’t get a loan from the bank. Why am I paying the bank interest for a property the bank never owned?

9. In life, mortgages are necessary evils, and interest is simply evil.

This picture is wrong! You have to develop properties evenly!
This picture is wrong! You have to develop properties evenly!

Because there are a finite number of houses and hotels, some players would hoard houses so others couldn’t use them. I learned, then, to buy houses and hotels as soon I could afford them.

10. In life, the early bird gets the worm and the house.

If you can’t pay your bills to the bank, the bank gets your properties and auctions them off to the highest bidder. If you can’t pay your bills to another player, the player has to pay the bank for mortgaged properties and develop them again. Once you are bankrupt, you’re done. There’s no Chapter 11 or 13. There is only one winner in Monopoly. There is only one top dog, one king of the hill, one champion—and the rest of the players are losers.

11. In life, even if you sometimes finish second, you’re still broke.

I learned who the negotiators were (my parents) and weren’t (my sisters) in my family. I learned who would overlook my rent either by not paying attention (Dad) or by choice (Mom). I learned who was most magnanimous (Mom) and who was cutthroat and wouldn’t take a single white dollar less than what was owed (older sister). I often tried to lose the game by overspending—and I ended up winning on rare occasions. I also learned that winning, though rare, was awesome if I bankrupted my sister to do it.

12. Competition can be healthy and fun—unless you have a vindictive sister.

I was often down to one of these.
I was often down to one of these.

Property values are important. You have to be vigilant to collect rent. Some “tenants” don’t want to pay. You must make them pay. You need property to make any real money in the game. You can mortgage properties to help pay your bills. If you improve your properties with houses and hotels, you can charge more rent. You can develop an entire side or a corner. You can make as decent a “living” owning smaller, cheaper properties as you could owning Boardwalk and Park Place. It’s easy to win and lose an auction, and sometimes winning an auction can lead to your downfall if you pay more than market value for the property. You have to build properties in a uniform way. You can’t have two vacant lots and a hotel. You have to build up the neighborhood.

13. In life, property is extremely valuable, and you must do your best to improve it.

At the beginning, the banker hands out $1,500 to every player. All are equals. You must spend this money wisely so it doesn’t run out. You stuff it under your side of the board in neat stacks or keep it in your fist so no one can tell how much you have. Whenever you land on a property no one owns, you count your money to see if you have enough. There’s no loan agreement to fill out. There’s no background check. Your credit score doesn’t matter. Either you have enough money or you don’t. I learned often what it felt like not to have enough. I also learned that as long as I kept moving around the board, I’d eventually get a payday.

14. In life, you must keep your mind on your money to mind your money successfully.

Unlike some people who gave up when they were down to their last dollar, I didn’t quit, playing until the often bitter end. I never gave up. I’d pray for a 3, 5, or 11 to get me through a gauntlet of hotels, sometimes rolling one die at a time. I’d pray to last until payday at Go for one more circuit of the board. I bargained with my creditors to accept a “Get out jail free” card instead of rent. I’d get down to my last white dollar or pink five-dollar-bill and pray for a miracle, hoping against hope that the next Chance card wouldn’t bankrupt me.

15. In life, perseverance and hope don’t always insure your survival, but you can’t survive in life without either.

The roll I'd inevitably get after landing on Park Place. Boardwalk and I were old pals.
The roll I'd inevitably get after landing on Park Place. Boardwalk and I were old pals.

The greatest life lesson

Perhaps the greatest life lesson I ever learned involved my parents, who allegedly played Monopoly on their honeymoon. My mother won handily, and my father made a decision then that he has never regretted to this day: My mother has been doing the bills and keeping their finances ever since. It was a lesson he passed down to me … but I’m not ready to give over those reins just yet.

My mind is still on my money. Monopoly taught me that.

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