What Authentic People Know About Winning

I spent the past week with my two ten-year-old grandchildren, Ethan and Holland. One of the activities we love to do together is play monopoly. I have to admit, rather embarrassingly, that when I pick up the dice for the first move, I transform from a kindly grandfather into a ruthless competitor. I become a callous, merciless, heartless, power-grabbing capitalist, lusting for control of Boardwalk and Park Place and as many other properties that I can get my hands on. And I understand something that the minds of ten-year-olds have yet to grasp: that it isn’t about money. I know that it’s about property. It’s about investment. The name of the game is acquisition. While the kids are hanging on to their money, I am going into debt to acquire more real estate – until I become the master of the board. In this game I take great pride in winning every bit of cash from these ten-year olds and see them give their last dollar and quit in utter defeat. What a moment of victory – to beat two ten-year olds in monopoly!

And then Ethan dejectedly looked up and reminded me, what I learned from the author John Ortberg years ago that, “it all goes back in the box.” All the houses and hotels, all the railroads and utility companies, all that property and all that wonderful money goes back in the box. Honestly, I didn’t want it to put any of it away. I wanted to leave the board out as a memorial to my ability to defeat two children.

But the game always ends and it always goes back in the box. Everyday, for somebody, the game ends. Whether you are a powerful CEO, an aging grandmother in a convalescent home, a brother with a brain tumor, a wealthy entrepreneur, or a young teenager who thinks their life will go on forever. Eventually, it all goes back in the box – the houses and cars, the titles and clothes, the big portfolios, the accumulated jewelry, the inheritance, the precious china, and the toys. It all goes back in the box.

In the end, it doesn’t matter what gets accumulated. What matters is how we play the game. What matters are the connections, the efforts, the challenges, and the joys. What matters is the encouragement and value we bring to others and the relationships we build along the way. What matters is how we grow and what we give, what we learn and what we teach. It’s about the memories and meaning, significance and sacrifice. It’s about the quality of our life through the service we render and how our life was lived.

It’s fun to win, and it’s good to learn how to lose, as long as we keep it all in perspective. Authentic people are comfortable enough with themselves to let go of their attachment to winning and sometimes lose in order to win. Keeping a good relationship with your grandkids is more important than winning a game. I only hope I can remember this next time we play monopoly.