When you carry a squash racquet in New York City, people admire you. They point you out on the subway and crouch beside their children to whisper, “He plays tennis!”

The game has a recognition problem, apparently. To be fair, though, it also has an image problem. Squash has long been synonymous with prep school, with being weedy and twee, and the most heinous clubs maintain an all-whites rule that encompasses the skin tone of their members. Full disclosure: I went to prep school, and grew up in the Caucasian Chalk Circle.

Yet squash isn’t just for douche bags. More than twenty million people worldwide play it, and Forbes has rated it the healthiest sport. You greyhound around a four-walled court to retrieve a ball caroming at a hundred miles an hour and send your opponent on the longest possible journey in return, then lunge into the far corner, where he’s sent your shot, and so on—and on, and on, and on, for an hour or more. It looks like tennis at triple speed, and feels like heroin without the needles and the nodding off and the vomiting afterward, except when you vomit afterward. The game, above a certain level of skill, is played at a lunatic extremity of effort.

The great Egyptian pro Amr Shabana once explained squash’s appeal after winning a gladiatorial match in London. Shabana, a slight, skittery lefty who clasps his racquet high on the handle, like a chef carving a roast, was everything I want to be on court—gracious, graceful, unpredictable, thirty-three. (I’m fifty-three.) Addressing the crowd from a nearly recumbent position, Shabana said, “By far, squash is the toughest, most brutal, most complete sport there is. It takes everything out of you. It takes every mental and physical effort you have. And if you do your best you have a fifty-per-cent chance to win.”

The game began in 1865, at Harrow School, in London, and proliferated throughout the British Empire, acquiring a mad-dogs-and-Englishmen burnish as it spread. (There was a court aboard the Titanic.) I’ve played it on a tea plantation in Sri Lanka and in the bowels of an old hotel in Kuala Lumpur. Most of the world’s best players still hail from Britain or its former colonies: where once the Pakistanis held sway, now the Egyptians do.

For a century, North America had its own brand of squash: a narrower court; a harder, more wounding ball. It was one of those American innovations, like Nascar or monolingualism, that failed to sweep the globe. My father taught me the hardball game when I was seven or eight, at the Tennis & Squash Club in Buffalo. We entered frosty courts by a secret hatchway and waved wooden racquets in majestic arcs, a ceremony akin to polar explorers chiselling out ice caves. Hardball squash was a Wasp birthright, something handed down along with seersucker, circumspection, and a reflexive way with a thank-you note.

I began taking squash seriously in my late twenties, when the more exacting global version took hold here. Three times a week, it provided me with exercise and an occasion for magical thinking—believing, for instance, that I played better after a haircut because I was more aerodynamic. I gradually got to be pretty decent: a cagey lefty with a deceptive forehand boast, a shot spanked into the sidewall that ricochets obliquely off the front wall just above the tin, squash’s version of a net. A few times in my thirties I even won the tournament at the Harvard Club, when the genuinely gifted players were busy with their version of Occupy Wall Street.

When I turned fifty, it was the chimes at midnight. The game I loved had begun to slip away, and I felt compelled to wrench it back—to see how much better at it I could still get. Or, rather, as I’d be seeking to improve while my body was rapidly disimproving, to see if I could learn how to cut my losses. Squash is a young man’s game; tournament draws are rife with dudes who bound on court, their earbuds leaking Imagine Dragons, eager to go far too fast for far too long. I do better with erratic college players, female pros who never quite reached the top, and anyone who has a mortgage. One of my regular partners, Cece Cortes, just retired, in her mid-twenties, at No. 62 in the world. She hits terrific rails—the staple shot that hugs the sidewall—and is springy as a Super Ball. But if I muster the will to endure, hanging around like Toshiro Mifune stuck full of arrows, I have a fifty-per-cent chance to win.

My goal was to crack the top ten of the over-fifties, nationwide. And my window was small. My wife, Amanda, and I had twins, Walker and Addie, and suddenly they were in grade school and I’d become hoodie dad. Addie had recently leaned in after we laughed at the same thing—a businessman tripping over his own briefcase—and told me, “The only bad thing about growing up is that we get closer and closer and closer to you passing away.” Two college friends had fallen (leukemia; a runaway car), and twentysomethings were looking right past me. I consoled myself that I was still slim, still energetic after three macchiatos, and that by the candlelight in a restaurant bathroom I looked fortyish. Forty-five, tops. (I looked fifty.)

The truth is, I was having the only thing more wearisome than a midlife crisis: a midlife slump. A crisis is at least vivid—the crimson Ferrari, the pink slip. A slump is just a gray mass of days. I would wake at 5 a.m., the hour of remorse, pinned by cares: overdue tax payments; overdue museum-permission forms; an overdue article; Roth I.R.A. regret. Sometimes I’d pad into the kids’ room to admire them as they slept: Addie clutching a stuffed penguin, Walker hand to heart, pledging allegiance. And then would come the disheartening recollection that, as vice-president of our co-op building, I had to find an exterminator for the rats that had chewed their way beneath our front stoop, along with a trapper for the squirrels scampering through gnaw-holes in the roof.

My path had become a rut. Unfortunately for my dreams of reinvention, squash itself was deepening it. After a match, my Achilles tendons felt like hawsers on a rusty barge, and as I clomped back to work I’d get passed by map-consulting tourists. At night, often as not, I’d bolt upright at 4 a.m., an hour before my scheduled remorse, with a searing calf cramp. Laboring groggily not to wake Amanda, I’d winch my calf over the side and stand to relieve the spasm. During this process, I more than once got tangled in the sheets and pinwheeled to the floor. So there were some issues.

In the movie version of this story, the training montage would go here. I’d have just lost a pivotal match—the match that made you understand, even before I did, that I had to change my life—following the death of my best buddy and/or my wife’s leaving me for a player so good that it’d be exhilarating when I beat him at the end. That battle would introduce you to squash’s rules (games are to eleven points, win by two, and a match is best of five games) and its strategy and protocols (you try to hold the center of the court, known as the T, while allowing your opponent a path to the ball).