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The Art of Winning and Losing

Playing a competitive sport as a teen allowed me to learn how to win and especially how to lose well…

I spent my tween and teen years playing sports—specifically karate and tennis. For karate, I earned my Second Degree Black Belt (I go into this more in A Kids Book About Confidence). I also played competitive tennis in high school—first on the Junior Varsity team for two years and then the Varsity team for the last two years. My team wasn’t the best in our area. In fact, we were one of the worst! We maybe won a match or two every season. Usually the schools in the “rich” areas won – with their access to and more budget for pro-level coaches (which we didn’t have).

So I got used to losing (a lot), but I still had the best time. Playing a competitive sport was so important for me as a teen and something that I think is important for my own kids to experience as well. The wins were few but they felt so good when they did happen. Playing a sport like that allowed me to learn how to win and especially how to lose well.

I think about that feeling of playing a game or match or some sort of competition, and it really doesn’t happen that often in your adult years. You might apply for a job and either get it or not. But you’re not seeing your opponent and competing against them face-to-face (imagine if you did?!) like you do when you play sports. Other than that, you might have a casual game night with friends or a game of one-on-one basketball in your driveway, but it’s not the same as playing on a team and playing against others.

Within the past year, I have started playing tennis regularly again. And I joined an Over-40 Women’s USTA Tennis League. While I could have just played tennis for fun with friends, something inside me missed competition and the desire to be part of something completely different than what I do on a daily basis. When you’re playing a sport, no one knows what you do for your job, how you parent your kids, or really anything beyond your skill on the court. It’s this alternative universe where you are just someone playing together or against each other for an hour or two. It’s a space for me to forget about anything else that I’m stressed or anxious about and rely on my brain and body to move and react. I don’t get paid for it, and I’m not the best on my team, but it brings me a level of calm that I really needed after these last couple crazy years.

Yesterday, I played my first doubles match for the season. I went into it feeling nervous. Could I win? Was I good enough to win? Or would I lose? And what if I lost by a lot? Would my teammates think I wasn’t good enough for the team? (Isn’t it funny how it doesn’t matter how old we get, we think the same things we did as when we were kids? Or at least I do sometimes). Tennis is a non-traditional “team” sport in that you’re not really all playing together as a team like you do in soccer or baseball. You’re playing either singles or doubles but then cumulatively, you’re still working to get more wins than losses. My first doubles match of the season was: 1-6, 6-3, 8-10. It was so close, and while we didn’t start off great, we ended strong and lost by 2 points in a tie-breaker. I was bummed to lose, but also felt great for getting that close to a win.

I came home, and my kids were excited to hear if I had won or not. When I told them I had lost, my oldest said, “I’m so sorry Mom! I’m sure that was disappointing for you.” But I used the opportunity to remind them that we’ll lose a lot in life—whether that’s a game, a match, or when things that just don’t work out. What’s important is that we learned from the experience, we think about how this loss can prepare us for what’s next, and that losing can still be a part of something you enjoy.


  1. This was beautiful, friend. A great lesson and reminder.

    Also the EQ of your kiddos is amazing. “I’m so sorry Mom! I’m sure that was disappointing for you.” They’re like little Brene Browns! (Loved her latest HBO special btw).

  2. This was helpful-and so true! As a mom of young kids, I remember when they realized they will not always win at every game. 😉 Helping them lose well is such an important skill! Thanks so much for sharing.


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