Winners Don’t Win, pt. 2

Winston, pt. 1

Whatever happens, stay emotionally invested in the point.
– Winston Philip Ramsay

If you put yourself in a place to win points with consistency, you still won’t make every shot, but odds are you’ll put yourself in a position to win the match. Your job on the court is not to win. Your job is to play in a winning way.

The paradox arises, then, that in order to win, your ultimate job is to learn to lose. Everybody – even Rafa and Serena – loses. Points. Games. Sets. Matches. Their minds.

No single shot wins a point. A beautiful winner by you, followed by 2 unforced errors, a double fault, and a winner by your opponent, only serves the game to your challenger on a silver platter. An overall approach and strategy focused on making as few mistakes as possible wins the game, the set, the match.

So, yeah, winners don’t win.

Cat’s and my brilliant tennis coach in New York City for the last couple years is Winston Philip Ramsay, former tour player, USTA development guru, head pro at the Knickerbocker Field Club, and Dean of Instruction at the Prospect Park Tennis Center, where pedestrian-player-schmucks like me are lucky to enjoy his wisdom.

We’ll be seeing a lot of Winston in this series, so I’m going to give over his first appearance here to his most important precept I carry on court every time I play. This lesson is not a shot, or a drill, or a method – but a mindset:

There are only 5 ways to win a tennis point.

  1. Your opponent hits long.
  2. Your opponent hits wide right.
  3. Your opponent hits wide left.
  4. Your opponent hits into the net.
  5. You hit a winner.

On the start of a point, if the serve is not an ace, all 5 outcomes have an equal chance of happening for both players.

Winning tennis has little to do with hitting winners.

Winners come when you recognize opportunities to create angles, put balls away, or to accelerate or decelerate an incoming ball. The choices you make on every shot are based on a host of observations you need to process as your opponent’s ball approaches you.

  • What’s the height of the ball?
  • What’s the ball’s pace?
  • What’s the ball’s angle?
  • What’s the balls’s spin?
  • Where is your opponent moving?

Height doesn’t always mean depth. Pace is relative to angle. Angle doesn’t always mean spin. Spin does different things to a ball depending on the other answers. Everything in front of you is in constant motion. The trick is to slow it all down, and let it roll. See where the sweet medley falls, as Sturgill Simpson says.

If everything comes together, then the shot you want, the shot your coach would want, and the shot you take are the same. In any shot sequence, you can’t count on those 3 things aligning, but you can bet that the shot you need to take will almost never be a winner.

Trying to force winners is a one-way ticket to losing. The game will never conform to you. This perspective may seem too reductive or Tennis 101, but in the heat of chaotic decision making out on the court, if you lose grip of fundamental principles, you put yourself in a mental no-man’s land. Getting lost in your head is a form of drowning.

To have faith is to trust yourself to the water. When you swim you don’t grab hold of the water, because if you do you will sink and drown. Instead you relax and float.

-Alan Watts

Discovering this mindset, one that I could take beyond the court, was the ultimate counterintuitive thrill when I came back to the game in 2021 after a 15-year hiatus. In my high wire high-school tennis team days, I never learned how to lose. Today, losing still stings, but I think I’ve grown enough that losing doesn’t stain.

Losing well is a critical skill in every facet of life. Losing teaches you way more than winning, by revealing the current depth of your humility and humanity. Winston opened me up to see I learned nothing of life from my game back then.

As a kid, I came at the game from the wrong direction – attempting to make the game conform to me. You can’t do that, because the game will not comply. On the one hand, I forgive myself almost all my youthful transgressions, since teenage brashness is as teenage brashness does.

With age and distance, iced with life experience, now I know how lucky am I to have the universe bend this way, to receive Winston’s instruction and turn it into action. He’s given me a true second act.

Every lesson with Winston travels upstream. “Your intention,” he will say at least once a session, “is always more important than the outcome.” A missed shot that was headed in the correct direction was still a good shot. It just means you beat yourself, which in a way is the worst way to lose, but also the easiest course to correct.

Tennis is a mental workout married to a physical beatdown, not unlike playing chess where you box a round between moves. The ability to take a punch is as important as landing one. Sometimes, you have to lose a little in order to win. Your opponents’ weaknesses often will not surface until you feel how hard they can hit you.

“Winning tennis” comes in 4 steps.

  1. Believe you can win the point.
  2. Create chances to win the point.
  3. Execute shots until the point is done.
  4. Let losing points roll off your back.

Just learn to lose.

Winners don’t win.

Simple, yes?

No matter what, it’s all going to be ok.