Chapter OneLearn Rule #1
This is our predicament.
Over and over again, we lose sight of
what is important and what isn't.
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
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
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
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. Plato
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. But you don't
even have to believe in the Bible to understand the lesson of the box.
Comedian Jerry Seinfeld put it like this:
To me, if life boils down to one significant thing, it's movement.
To live is to keep moving. Unfortunately, this means that for the
rest of our lives we're going to be looking for boxes.
When you're moving, your whole world is boxes. That's all
you think about. "Boxes, where are the boxes?" You just wander
down the street going in and out of stores, "Are there boxes here?
Have you seen any boxes?" It's all you think about.
You could be at a funeral, everyone around you is mourning,
crying, and you're looking at the casket. "That's a nice box. Does
anybody know where that guy got that box? When he's done with
it, you think I could get it? It's got some nice handles on it. My
stereo would fit right in there."
I mean that's what death is, really-the last big move of your
life. The hearse is like the van, the pall bearers are your close
friends, the only ones you could really ask to help you with a big
move like that. And the casket is that great, perfect box you've
been looking for your whole life.
What Really Matters?
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, preoccupied 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.
As a student in school, I may think that the game is won by
getting better grades or making first string or getting elected class
president. Then comes graduation 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 it enough? Did I do good? And sometimes if I'm quiet: Does it
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
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, Anne Lamott writes, but left to
our own devices, we seek all the worldly things-possessions, money,
looks, and power-because we think they will bring us fulfillment.
"But this turns out to be a joke, because they are just props, and when
we check out of this life, we have to give them all back to the great
prop master in the sky. They're just on loan. They're not ours." They
all go back in the box.
Live Differently-Starting Now
Human beings are the only creatures whose frontal lobes are so developed
that they know that the game will end. This is our glory, our
curse, our warning, and our opportunity. In Jerusalem, hundreds of
synagogues have been built by Jews from around the world. One was
built by a group from Budapest, and according to an ancient custom,
they had a coffin built into the wall. There is no body in it, they explain
to visitors; it is present as a silent witness to remind us that it
all goes back in the box.
The Talmud teaches that every person should fully repent one day
before his death. When a visitor asked, "But how will I know when
that day is?" he was told: "Treat every day as if it were the day before
your last." Arrange your life around what matters most. Starting
today. The box will wait.
This is how my grandmother taught me to play the game of my
life, and I talk about that in the pages that follow. 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 named-I'm not
making this up-Hack, Jack, and Mac (the names Huey, Dewey, and
Louie already having been taken by Donald Duck's nephews), and
then three girls, including my mother. She never moved outside the
state where she was born. The only paid job she ever had that I know
of was working behind the counter in a little Swedish bakery.
She was content with her life because she believed she knew what
mattered. She had a clear understanding about what she thought was
temporal and what was eternal. Everybody has to decide what he or
she believes constitutes winning and losing in life. One of the smartest
men who ever lived told one of his most unforgettable stories
about exactly that decision. That's for the next chapter. But I have
had a long time to think about it.
My grandmother taught me how to play the game.