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Winning at Losing

 But seek first the kingdom of God and his righteousness, and all these things will be added to you. – Matthew 6:33 ESV

Thoughts from losing on the pickleball court.


Sometimes the best life lessons come in unexpected places. Our new neighborhood has a pickleball court, and some friendly pickleballers invited me to join their ranks, even though I had never played before. Today’s missive includes some observations from playing pickleball. More precisely, losing at pickleball.

Growing up, I was the youngest of four boys. Much has been written about the ramifications of birth order. The things I’ve read have generally disparaged those of us who are the last-born. We have been described as master manipulators, charming, and adept at getting what we want. We are accused of “working the system” with a well-timed smile or a strategically deployed cute remark. To that I say, “No comment.” One indisputable fact is that I became very proficient at losing while playing with three older brothers.

I lost at everything. Football, baseball, basketball, cards, checkers, chess, board games—you name it, they beat me. So losing at pickleball is in my wheelhouse. Those early losses trained me not just in humility, but in redefining what counts.

How does someone who has experienced so much failure survive in our ‘winner take all’ culture? You simply find better ways to keep score and redefine what winning is. This is not a comment supporting the proliferation of participation trophies. I’m all for keeping score. I love that we keep track of things; I greatly enjoy winning a pickleball game. But I also find a lot of satisfaction even when I lose—because I don’t let the final score define me or the experience.

By default, the world will tell you who you are and what to value. “Winning isn’t everything; it’s the only thing” is a well-known quotation in sports. It is attributed to UCLA Bruins football coach Red Sanders, and later to Vince Lombardi. It’s a lie of the scarcity mindset of the culture. This lie has become so woven into our cultural fabric that the team that places second out of the 32 teams in the NFL is labeled a loser each year. Their shame is the stuff of legends. Ask any Buffalo Bills fan. Getting to the Super Bowl is no small achievement, but in our culture, you aren’t a winner until they say you are. To that I say, “Baloney.”

Don’t let someone else tell you who you are, your worth, or your life purpose. Unless that someone else is Jesus, who I believe provides a unique and profound understanding of our identity and worth. In his Sermon on the Mount, he emphatically taught his listeners not to worry about or run after the things of this world, because our Father in heaven knows we need them and longs to see us flourish. He is a good Dad, and his Kingdom is one of abundance. The key metric on Jesus’ scorecard was to seek God’s kingdom and righteousness first. I put Matthew 6:33 at the top of mine, too. It’s not possible to win at life without it.

Kingdom First Abundance

  • Deriving great pleasure from hitting a good shot or doing great work.

  • Developing relationships with neighbors or colleagues.

  • Playing outside, soaking up vitamin D, or walking with a spouse, child, or friend.

  • Being considerate and keeping things moving. Lighten up, find the joy.

  • Staying upright—no one gets hurt. Protecting one another physically and emotionally.

  • Great sportsmanship, meeting at the net, congratulating the winners, and celebrating the game or someone else’s accomplishment.

If Vince Lombardi were alive today and playing pickleball, he might say, “Going home unhurt and in one piece isn’t everything, it’s the only thing.”

Create your abundant life scorecard. Ensure it begins with seeking first the Kingdom and his righteousness.

Run the play.

“… our Father in heaven knows we need them and longs to see us flourish. He is a good Dad, and his Kingdom is one of abundance.”

Finding Our Place in the Story

What experiences have reshaped your definition of “winning” or success?

Can you recall a moment when losing led you to gain something more valuable?

How does recognizing your worth beyond worldly standards influence your daily interactions? Has it helped you see God more clearly through their poverty or faith?

Time for a laugh? Pickleball Fails Video

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