Winning is Confusing — SS #26

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Winning is the most confusing thing in tennis.

Why?

Because players have no idea what’s going on.

And sometimes a win doesn't tell the whole story

They walk off the court with a W next to their name but an L next to their comprehension.

They don’t understand the long-term implications of their wins, and this gives them a skewed view of their progress and potential.

Tennis in that way is a fascinating sport because we are not measured against objective times or markers. It’s not like we’re swimmers or sprinters racing against a clock or a definitive time.

No.

The only thing we are measured against is our opponent. We are only compared to the person across the net from us.

That’s it.

The Under-14s Champ

Consider the story of the under-14s champ. Let’s call him Steven.

He wins everything.

He’s known around the local tournament circuit as that kid who always makes it to the finals or takes home the silverware.

His dresser at home is piled high with two-inch trophies and inconsequential medals. There’s so many of them that dad has had to install a floating shelf off amazon.

His parents proudly declare to anyone who listens that little Steven is on his way to the highest levels of tennis. That he won this under-14s tournament, and that he’s in the top 100 nationally. Blah blah blah.

They’re climbing the side fences of tennis courts every time Steven’s on the court, cheering with each point won and scowling with each game lost.

But there’s a big problem for Steven.

Do you know what it is?

It’s the way Steven wins.

The 13 under-14s trophies he polishes every weekend; how did he win them?

By lobbing the ball 20 feet into the air and camping out 10 feet behind the baseline.

By pancaking in pathetically slow serves.

By running down each ball and pushing it into the middle of the court.

By always waiting for his opponent to miss.

Because tennis is a fascinating sport.

It’s a game of getting the ball into the court one more time than your opponent.

And there are several ways one can do this.

The way that’s most prevalent at the junior levels? Just lob it in really high again and again and wait for your opponent to self-destruct.

Smart. Intelligent. But very short-term oriented.

Because the truth is that players who learn to win this way are often only successful in their younger years.

As they get older, they start to find that their peers who were guided towards long-term development and playing forcing tennis are suddenly beating them.

Pushing the ball in again and again will only take you so far in tennis.

What’s worse, Steven has made this style of play automatic. It’s how he’s taught himself to win. So when he’s tight and nervous, when it really counts, do you think all of a sudden he’s going to start hitting the ball well or try to force errors from his opponent?

Or is he going to revert back to what’s given him success in the past: pushing, lobbing, waiting for the opponent to miss? This doesn’t set him up for long-term success. It sets him up for a plateau.

How you play—especially in the most stressful moments—is what you make automatic.

Steven’s reliance on pushing and lobbing works perfectly—until one day, it doesn’t.

As he moves up in age and his peers grow stronger, taller, and more skilled, Steven starts losing to players who punish his high, weak balls. It becomes harder to lob a kid who’s 5’11” as opposed to one who’s 4’11”.

It’s a rude awakening, and suddenly, the medals on his dresser start gathering dust.

As the years go by, no new trophies join the collection.

The Club Warrior

We can also map this story onto the weekend club warrior.

You may be winning at the 3.5 or 4.0 NTRP level… but how are you winning?

Are you playing aggressive, percentage tennis?

Or are you relying on just getting one more ball back into the court—thinking that you can move up to the 5.0 level eventually because you’re cleaning up at the lower levels?

If you’ve experienced a jump between levels, you’ll realize that the better players don’t just roll the ball into the court.

They apply their patterns on you and rarely make you feel comfortable when the point is on.

I have been on the court with players who are now in the top 100, and what stood out to me the most was how much pressure I felt if I didn’t get the ball to land a foot within the baseline.

And even if the ball was deep, if it was slow, I knew that I would be punished.

Going back to the club warrior, it’s easy to fall into the trap of thinking, “If I just win, everything’s fine.”

But when you focus only on winning, you could be reinforcing habits that might help now but won’t work when you face higher-level players.

Prioritize How You Play Over Victory + The 2-Year Plan

So how should you think about winning?

How should one navigate this process?

If you really want to think about long-term development, you need to prioritize how you play over winning and losing.

And I want to be really clear here, I’m not saying that you should be tanking your matches, just bashing the ball as hard as possible, while trying to tell yourself you’re trying to be a better player.

A common framework I use with my players is to ask them: “What kind of player do you want to be in 2 years? How do you want to play in 2 years? What do you want to make automatic in your game in 2 years?”

I find that by encouraging a long-term, growth-oriented mindset, players are more likely to take risks, push themselves toward being uncomfortable, and potentially even try new skills in match play.

Skills that they might have been too scared to trial if they were too focused on winning that match right there and then.

Goal setting is critical here. By the time you’re in the heat of the moment and playing the match, it’s usually too late to have this long-term focus on your decisions and playing style. You’ll be too caught in the moment and might revert to what is safe and comfortable.

But if you plan process and performance goals appropriately, you can rely on them to help you compete in a way that’s more becoming of the player that you want to be in two years.

What’s a simple example? If you want to add being an all-court aggressive player to your skillset, commit to approaching the net every time the ball lands inside the service box. Take the time to write this down, maybe even visualize a successful performance of this, and assess how you did after the match with this goal, too. (You must also practice this a few times in open play or practice sets, by the way, if you want to be successful when it really counts.)

This is just the tip of the iceberg.

If you’re curious about how to start building long-term, sustainable improvements in your game, I can help you. We can work on refining how you play now, so you’re not just winning today but developing the skills to win tomorrow.

More than fixating on winning at any cost—start thinking about winning by playing the right way.

P.S.: I first heard this term, “Winning is confusing,” from Steve Smith of GreatBase Tennis. I have expanded it a little in this newsletter.