Rediscovering Life’s True Game: It All Goes Back in the Box

John Ortberg’s grandmother was an incredible Monopoly player. When he was young, she would win everything — Boardwalk, Park Place, the lot — while he was left with nothing. And she would get this grin on her face and say, “John, someday you’re going to learn how to play the game.”

One summer, when he was about thirteen, a boy moved in next door who was a brilliant Monopoly player. John practised with him every single day, because he knew his grandmother was coming in September.

When Grandma arrived, he ran into the house, hugged her, and said, “Grandma, how about a game of Monopoly?” Her face lit up. “Let’s go, John.”

He was ready for her this time. He wiped her out. He said it was the greatest day of his life.

And then his grandmother said, “Now you know how to play the game. Let me teach you a lesson about life. It all goes back in the box.“

Everything you bought, everything you accumulated — all of it. If your life is only about how much money you make, your recognition, your power, then at the end, it all goes back in the box. Nobody wants their net worth on their tombstone. What they want to know is that they made a difference. The only thing you carry out of the game is who you loved, and who loved you.

Keeping score where it really counts

In Ortberg’s telling, a childhood game becomes a profound metaphor for life’s deepest truths. The pivotal moment isn’t the winning — it’s the wisdom that follows it. True fulfilment lies not in what we accumulate but in what we invest in relationships and in nurturing the soul.

His message asks us to shift from fleeting success to enduring significance. It challenges the idea that our self-worth is tethered to wealth, recognition, or power, and argues instead for a life anchored in generosity, service, and love.

In a world driven by materialism and the pursuit of status, that is a timely reminder of what actually matters. Live with the long view in mind. Make choices aligned with your deepest values. Cultivate the connections that will outlast every trophy.

From success to significance

One of the things that drives people to become self-serving is the belief that their worth is a function of how much money they make, the recognition they receive, and their power and status.

Let me be clear: there is nothing wrong with making good money. There is nothing wrong with being recognised for your efforts. There is nothing wrong with holding a position of influence.

But if that is who you think you are — if your self-worth lives there — then the only way to keep it is to get more. More money, more recognition, more power. It becomes a cycle you can never win, and it quietly pushes you to put yourself ahead of everyone else. We have all seen the executive collecting a bonus in the same quarter as mass layoffs. That is success mistaken for significance.

Real fulfilment lives on the other side of that trade:

• In place of chasing money, generosity.
• In place of chasing recognition, service — finding purpose in what you do for others.
• In place of chasing power and status, meaningful connection and loving relationships.

The move from success to significance is an invitation to step past the surface trappings and build a life rich in purpose, service, and genuine human connection.

So here is the question I sit with, and offer to you: when the game is over and it all goes back in the box, what will you have kept?