Playing someone you’re supposed to beat can be a nerve-wracking experience. But it will teach you the most important skill in tennis: How to win

Once upon a time, on the nights before I was supposed to play a certain opponent, I would lay awake hoping, somewhere deep down, he would text to tell me he had to cancel.

Why would I agree to play someone, if I secretly hoped our match wouldn’t happen? He was a friend, first of all, and an engaging conversationalist. He liked to delve into the finer points of tactics, and cheerfully enumerate his many deficiencies. He made tennis fun.

There was only one problem: I almost always beat him.

It wasn’t that we weren’t competitive. He won sets, and pushed me in others. He had taken up the sport late, and had the unpolished strokes to show for it, but this only made him a more cunning competitor. Compensating for his stylistic shortcomings, he found clever, unorthodox—and sometimes infuriating—ways to move his opponents out of position. He gave everything he had, and forced me to play my best to win.

“I don’t know why I can’t beat Tignor,” he told a mutual friend. When that exasperated comment was relayed to me, I found myself wondering the same thing. He often beat other players in our group who would turn around and beat me the following week.

You might think I would have relished our encounters, but no one made me as nervous. Losing would have meant slipping down a notch on the local tennis totem pole, and word of the upset would have made the rounds. On the mornings of our matches, I would cast about for a reason, any reason, why I shouldn’t care about the result.

“It’s just a casual game between friends,” I’d think as I got dressed. “Nothing official.”

Sipping my coffee, I’d appeal to my sensible side.

“What’s the big deal about losing one time? He’s due. He’s overdue.”

Driving to the courts, I’d take a more philosophical tack.

“You play tennis for exercise; that’s all that counts,” I’d say, a little sternly, hoping the idea would stick.

During the warm-up, I’d recall the advice of so many mental gurus: “Focus on the process, and the result will take care of itself.” As I recited this calming mantra, my nerves would finally dissipate and my shots would flow.

Or so I thought.

"In many sports, such as tennis, one player’s superiority over another is quickly established and monotonously reaffirmed,” the author John Updike wrote.

A golf fanatic, Updike was comparing tennis unfavorably with his favorite sport, in which handicaps theoretically level the playing field. But even at its most one-sided, tennis isn’t as straightforward as he made out. Playing someone you’re supposed to beat can be one of the game’s great psychological challenges.

It’s also one of the most undervalued. Aspiring players are told to “play up” against better opponents whenever they can, and this is indeed an essential part of improving. But so is playing down. Unlike golf, tennis is about more than just executing your shots and performing your best. It also requires you to defeat someone, to make another player capitulate. This is a skill of its own, and one you don’t often get to hone against superior opponents.

Playing down also forces us to deal with another, insidious adversary: Expectations, both our own and those of people around us. Because there’s no shame in losing to a better player, we never feel the same pressure, the same need, to beat them.

“Players tend to obsess over rankings and ratings of any kind,” says Jeff Greenwald, a sports psychologist and author of The Best Tennis of Your Life: 50 Mental Strategies for Fearless Performance. “‘What are people going to say if I lose to someone below me?’ ‘What if I get dropped off my league team?’ The first thing people ask when you walk off the court is: ‘Did you win?’”

In the age of UTR, when classifications are more hyper-specific than ever, our knowledge of who we “should” beat, and our sensitivity to our status, have only been heightened.

“Should is a six-letter swear word in tennis,” Greenwald says. “Players who have that ego investment may fear a negative end result, and stop focusing on the task at hand.”

To combat this dynamic, Greenwald has a set of recommendations to help you “change the channel” and shift your mindset:

• “Instead of worrying about what’s going to happen, ask yourself, ‘What’s going to help me win?’”
• “Give yourself two simple intentions that will keep you in the flow of the match, such as ‘breathe between points’ or ‘play on your own terms.’”
• “Visualize successful shots based on your tactics. The more players focus on their intentions, the less focused they’ll be on their nerves.”
• "Respect your opponent’s game, whatever it looks like. People go ballistic when they have to play ‘pushers.’ You won’t beat them if you’re bothered by them.”

“The main strategies I have players employ in this situation are not that different than what I have them do consistently during competition,” Greenwald says.

The goal of changing the channel is to make a match against a lower-rated player feel like any other match: One you want to win, rather than one you’re scared to lose.

That shift, from apprehension to determination, turned out to be key for me. When I cut away from my own “match I’m supposed to win” story earlier, I was in the process of trying to execute my strokes and let the result take care of itself. Whenever I adopted this mindset, I hit the ball well. But something odd happened: My good shots didn’t win me many points. I settled for rally balls, instead of looking to create openings. My approaches sat up and I was passed. I let my opponent drag me back and forth with his drops and slices. I worked so hard to pretend that I didn’t care about the result, I started to believe it.

Focusing on the process wasn’t enough for me. To win I needed to think of the outcome, too. Only when I fell behind, and the prospect of defeat became real, did I find the edge I needed to grab control of the match.

From then on, I played more decisively, I looked to end rallies at the first opportunity, I didn’t allow my opponent to dictate with the patterns he liked. Instead of trying to ignore my nerves, I used them. Instead of worrying about what other people would think, I forgot all about them and followed where my competitive energies took me.

“For some players, determination to win can narrow your focus and give you a mission,” Greenwald says. “Sometimes it can help to visualize success when belief is low. It may seem like a contradiction, but it’s reflective of the nuances and differences in people’s mindsets.”

Can process- and outcome-based approaches work in harmony? Can you compete your hardest without bringing your ego into play? Timothy Gallwey, author of The Inner Game of Tennis, thought so.

“Winning is overcoming obstacles to reach a goal,” he wrote. “Each player tries his hardest to defeat the other, but in this use of competition, it isn’t the other person we are defeating; it’s simply a matter of overcoming the obstacles he presents.”

When we think of overcoming obstacles in tennis, we think of beating better players. But the opponents we regularly beat also confront us with hurdles. They make us deal with strange shots and spins. They swing freely, because they have nothing to lose. They inspire us to live up to our own expectations. They teach us the difference between playing well and winning.

Eventually, with lessons, my friend improved, and I took a few more losses. Rather than feeling like the end of the world, those defeats made my wins more satisfying—I’d scaled a higher obstacle. Whatever the result was, when our sessions were over, I was always happy he hadn’t canceled.