My grandmother had just gotten out of jail.

She was a roll away from the yellow properties. And the yellow properties meant trouble. They were mine. And they had hotels. And Gram had no money. She had wanted to stay in jail longer to avoid landing on my property and having to cough up dough she did not have, but she rolled doubles, and that meant her bacon was going to get fried.

I was a ten-year-old sitting at the Monopoly table. I had it all—money and property, houses and hotels, Boardwalk and Park Place. I had been a loser at this game my whole life, but today was different, as I knew it would be. Today I was Donald Trump, Bill Gates, Ivan the Terrible. Today my grandmother was one roll of the dice away from ruin. And I was one roll of the dice away from the biggest lesson life has to teach: the absolute necessity of arranging our life around what matters in light of our mortality and eternity. It is a lesson that some of the smartest people in the world forget but that my grandmother was laser clear on.

For my grandmother taught me how to play the game….

Golda Hall, my mother’s mother, lived with us in the corner bedroom when I was growing up. She was a greathearted person. She was built soft and round, the way grandmothers were before they took up aerobics. She remains, at least in the memories of my boyhood, the most purely fun person I have known. She let us stay up later than we were supposed to on Friday nights when our parents were gone. She peeled apples for us, told us ghost stories and scary old poems (“Little Orphan Annie came to our house to stay …”) that kept us awake for hours. She baked banana bread that was like having dessert for breakfast and made us red velvet cake—which consists mostly of butter—on our birthdays.

And she taught me how to play the game.

My grandmother was a game player, and she did not like to lose. She didn’t get mean or mad, but she still (to use an expression from her childhood world) had some snap in her girdle. It was part of her charm. Every Friday night as long as my grandfather was alive, the whole family, including spouses, would gather to play a card game called Rook; and if you were Gram’s partner, it was not wise to miss a trick or lose the bid. Everyone’s favorite old home movie featured Gram playing in a softball game at a family picnic in her younger days. She made contact with the ball and ran the bases with such singleness of purpose—a large woman coming at you like Bronco Nagurski—that no one got in her way. Home run. When she played Chinese checkers with small grandchildren, she was not one of those pushover grandmothers who would lose on purpose to make the grandchildren feel better about themselves. Gram believed before Max De Pree ever said it that a leader’s first task is to define reality. She was the leader, and the reality was that she played to win. Pouting and self-pity, two of my spiritual gifts, did not elicit sympathy from her, for even when she was playing, she kept an eye on what kind of person you were becoming. And my grandmother taught me how to play the game.

The Master of the Board

Grandmother was at her feistiest when it came to Monopoly. Periodically leaders like General Patton or Attila the Hun develop a reputation for toughness. They were lapdogs next to her. Imagine that Vince Lombardi had produced an offspring with Lady MacBeth, and you get some idea of the competitive streak that ran in my grandmother. She was a gentle and kind soul, but at the Monopoly table she would still take you to the cleaners.

When I got the initial $1,500 from the banker to start the game, I always wanted to hang on to my money as long as possible. You never know what Chance card might turn up next. The board is a risky place. I am half Swedish (on my father’s side), and Swedes are not high rollers.

But my grandmother knew how to play the game. She understood that you don’t win without risk, and she didn’t play for second place. So she would spend every dollar she got. She would buy every piece of property she landed on. She would mortgage every piece of property she owned to the hilt in order to buy everything else.

She understood what I did not—that accumulating is the name of the game, that money is how you keep score, that the race goes to the swift. She played with skill, passion, and reckless abandon. Eventually, inevitably, she would become Master of the Board. When you’re the Master of the Board, you own so much property that no one else can hurt you. When you’re Master of the Board, you’re in control. Other players regard you with fear and envy, shock and awe. From that point on, it’s only a matter of time. She would watch me land on Boardwalk one time too many, hand over to her what was left of my money, and put my little race car marker away, all the time wondering why I had lost yet again.

“Don’t worry about it,” she’d say. “One day you’ll learn to play the game.”

I hated it when she said that.

Then one year when I was ten, I spent a summer playing Monopoly every day with a kid named Steve who lived kitty-corner from me. Gradually it dawned on me that the only way to win this game was to make a total commitment to acquisition. No mercy. No fear. What my grandmother had been showing me for so long finally sank in.

By the fall, when we sat down to play, I was more ruthless than she was. My palms were sweaty. I would play without softness or caution. I was ready to bend the rules if I had to. Slowly, cunningly, I exposed the soft underbelly of my grandmother’s vulnerability. Relentlessly, inexorably, I drove her off the board. (The game does strange things to you.)

I can still remember—it happened at Marvin Gardens.

I looked at my grandmother—this was the woman who had taught me how to play. She was an old lady by now. A widow. She had raised my mother. She loved my mother, as she loved me. And I took everything she had. I destroyed her financially and psychologically. I watched her give up her last dollar and quit in utter defeat.

It was the greatest moment of my life.

I had won. I was cleverer, and stronger, and more ruthless than anyone else at the table. I was Master of the Board.

But then my grandmother had one more thing to teach me. The greatest lesson comes at the end of the game. And here it is. In the words of James Dobson, who described this lesson from Monopoly in playing with his family many years ago: “Now it all goes back in the box.”

All those houses and hotels. All that property—Boardwalk and Park Place, the railroads and the utility companies. All those thousands of dollars. When the game is over, it all goes back in the box.

I didn’t want it to go back in the box. I wanted to leave it out as a perpetual memorial to my skill at playing the game—to bronze it, perhaps, so others could admire my tenacity and success. I wanted the sense of power that goes with being Master of the Board to last forever. I wanted the thrill of winning to be my perpetual companion. I was so heady with victory after all these years that for a few moments I lost touch with reality. None of that stuff was mine—not really. Now, for a few moments, it was my turn to play the game. I could get all steamed up about it for a while and act as if the game were going to last forever. But it would not. Not for me. Not for you either. Plato3 said that the entire task of philosophy can be summed up as melete thanatou—“mindfulness of death.”

I am a Christian, and I seek to write this book from the perspective of faith. I believe that you are a ceaseless being with an eternal destiny in the universe of an unimaginably good God.

John Ortberg, When the Game Is Over, It All Goes Back in the Box (Grand Rapids, MI: Zondervan, 2008).

We have just released a new Bible Study based on John Ortberg’s Book, When the Game is Over It All Goes Back in the Box, by John Ortberg.

These lessons are available on Amazon, as well as a part of my Good Questions Have Groups Talking Subscription Service. Like Netflix for Bible Lessons, one low subscription gives you access to all our lessons–thousands of them. For a medium-sized church, lessons are as little as $10 per teacher per year.

Lessons include:

Lesson #1
Chapters 1 – 2
Learn Rule #1
Be Rich Toward God

Lesson #2
Chapters 3 – 4
Three Ways to Keep Score
Master the Inner Game

Lesson #3
Chapters 5 – 6; Untie Your Ropes
Resign as Master of the Board

Lesson #4
Chapters 7 – 9
No One Else Can Take Your Turn
Remember Your Stuff Isn’t Yours
Prevent Regret

Lesson #5
Chapters 10 – 11
Play by the Rules
Fill Each Square with What Matters Most

Lesson #6
Chapters 12 – 14
Roll the Dice
Play with Gratitude
Find Your Mission

Lesson #7
Chapters 15, 16
Beware the Shadow Mission
Two Cheers for Competition

Lesson #8
Chapters 17 – 19
More Will Never Be Enough
Winning Alone Is Called Losing
Be the Kind of Player People Want to Sit Next To

Lesson #9
Chapters 20 – 21
Collect the Right Trophies
The King Has One More Move