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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.  She was the Master of the Board!

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. She was in control. Other players regard her 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 on 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 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, and 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.

And then she had one more thing to teach me. Then she said, “Now it all goes back in the box–all those houses and hotels, all the railroads and utility companies, all that property – Boardwalk and Park Place, and all that wonderful money–now it all goes back in the box.”

I didn’t want it to go back in the box. I wanted to leave the board out, bronze it maybe, as a memorial to my ability to play, and win, the game.

“No,” she said, “None of it was really yours. You got all heated up about it for a while, but it was around a long time before you sat down at the board, and it will be here after you’re gone. Players come and players go. But it all goes back in the box.”

And the game always ends. For every player, the game ends.

It’s not bad to play the game. It’s not bad to be really good at it. It’s not bad to be Master of the Board. My grandmother taught me to play to win.

But, there are always more rungs to climb, more money to be made, more deals to pull off. And the danger is that we forget to ask what really matters. We race around the board with shallow relationships, frenzied schedules, pre-occupied souls. Being smart or strong does not protect you from this fate. In some ways, it makes the game more dangerous, for the temporary rewards you get from playing can lull you into pretending that the game will never end.

Every day includes the obituaries of people for whom this week the game ended. Skilled businessmen, an aging grandmother who was in a convalescent home with a brain tumor, teenage kids who think they have the whole world in front of them, and somebody drives through a stop sign. It all goes back in the box–houses and cars, titles and clothes, filled barns, bulging portfolios, even your body.

As a student in school, I may think that the game is won by getting better grades, making first string, or getting elected class president. Then graduation arrives and the pressure to win at my job, to get promoted, to have enough money, to feel safe, and to be able to think of myself as successful. I pass somebody up and feel pleasure. Someone passes me, and I feel a stab of pain. Always I hear this inner voice: Is this enough?. . .  Did I do good? And sometimes if I’m quiet: Does it mean anything?

Then the chase is for financial security, a well-planned retirement in an active senior community where Botox and Grecian Formula and ginko biloba and Lipitor and Viagra bring chemically induced temporary immortality.

Then one day it stops. Other people keep going. Somewhere on the board, somebody is just getting started. But for you, the game is over. Did you play wisely? We all want God, but left to our own devices, we seek possessions, money, looks, power – thinking they will bring us fulfillment. But they all turn out to be just props. Props, that when we check out of this life, all go back to the great prop master. They’re just on loan. They’re not ours. They all go back in the box.

This is how my grandmother taught me to play the game of my life. My grandmother led, in many ways, a pretty simple life. She never went to high school, never led a company, never wrote a book, never traveled the world. She met her lifelong sweetheart in the eighth grade, her last year of formal education. She gave birth to three sons and then three girls, including my mother. She never moved outside the state where she was born. The only paid job she every had, that I know of, was working behind the counter in a little Swedish bakery.

She was content with her life because she knew what mattered. She had a clear understanding about what was temporal and what was eternal. She knew how to play the game.

From It All Goes Back in the Box by John Ortberg (2007)