When my midlife crisis hit, I didn't need to buy a Harley—I needed to be a caddie. And there was only one place to do that: the wild and soggy coasts of Scotland.

Don J. Snyder

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A WELL-TRAINED CADDIE working in Scotland will carry for himself and his golfer: tees, divot tool, small coin for marker, pencil, extra scorecard, lighter, wool cap for when the wind howls off the North Sea, sunscreen (seldom needed), large towel with one end kept wet to clean clubs and ball, wee towel kept dry at all costs beneath his clothing and used only for grips (often needed), sandwich for when he’s sent straight from the 18th green back to the first tee for a second loop, small bottle of water he can refill around the course as needed, waterproof top and bottom, a pharmacopoeia of drugs for aches and ailments (because it is a point of honor never to call in sick during the 233-day season), pin sheet, and yardage book, though he knows the ground by heart. In addition, of course, he carries his golfer’s clubs, and because the game can wreak havoc on the mind, there are times when he carries his golfer as well, and learns what it really means to be a caddie.

I had a 2:40 p.m. round one late-September afternoon at Kingsbarns Links, just outside legendary St. Andrews, Scotland, “the home of golf,” and was talking outside the caddie shed with the three guys going out with me, until we heard Davey Gilchrist, our caddie master, call to us, “Up you go, boys.” We paused to dip our towels in the blue bucket before we made our way to the clubhouse. “Once more into the breach,” one boy said. “Off on another blind date,” I replied. At 57, I was 20 years older than most of the other caddies. A little old for blind dates. But that was how I had come to think of these four-and-a-half-hour excursions with strangers.

The rest of the way to the clubhouse, we were silent, distracted by the weather the way sailors are, each of us already taking note of the wind and making silent calculations about how we would play the first hole. My golfer, a trim American, maybe 40, in an elegant pink shirt that Jay Gatsby would have admired, was a bit nervous, and thus too quick at the top of his backswing. He hooked his drive into the rough about 230 yards away.

“Is that gone?” he asked anxiously as he glared into the distance.

“I’ve been there before,” I told him. “We’ll find it.”

His second shot disappeared in a gorse bush, and after three putts he took double bogey. At the second tee, he overcooked a six-iron onto a par-three green, sending the ball so far off the back side that, as veteran Scottish caddies say, Lassie couldn’t have found it if it was tied to a piece of bacon. From there, a scuffed wedge into a bunker, a bladed wedge, two putts, and I could tell by his face that he wanted to go home. Or anywhere. He had planned this trip for years, a pilgrimage to the holy land of golf, and now he was in hell.

There is no other enterprise like golf. Imagine that every time you rode your bicycle to the store for a newspaper, you knew for a fact that you’d be thrown over the handlebars without warning sometime before you got home. Only romantic love can turn on you so certainly and cruelly.

On the third tee, I kept my instructions short “Just take it down the left side” then walked away to give both of us some room to think. Him about how he needed to make his first real swing of the day, and me about how I got here.

ONE HUNDRED AND SEVENTY-TWO days earlier, almost half a year, I’d stood on the first tee of Kingsbarns trying to decide if it was a two- or a three-club wind blowing out of the north so I could begin to prove myself a worthy caddie. The last time I’d carried someone else’s bag I was 14, and I went straight from the course with my five dollars to buy the Beatles’ first album. It had been a long road back. I had spent most of the intervening years barricaded in rooms from Canada to Northern Ireland, writing eight books and two movies, while my wife and I raised four children. Now, with three of them in college, I needed a second job.

That’s the easy explanation for what took me to Scotland. The more complicated one is that, unlike my wife, who was taking the kids’ leaving home in stride, I was suffering. The emptying rooms, the quiet house, the dog looking at me all the time for some kind of explanation you expect that part and you brace yourself for it. I had when my first two daughters left. But then my son, Jack, left for the University of Toledo, a million miles from our home in Maine, and made the golf team as a walk-on. That October, when he was playing his first season, I was watching the Golf Channel’s presentation of the Alfred Dunhill Links Championship, a big autumn event on the European Tour, which is held at Kingsbarns. Just one year earlier, Jack had watched it with me and we’d made our secret pact: He would play on the pro tour one day, and I would learn to be a caddie so I could carry his bag.

My wife came down the stairs and found me alone in front of the tube, wearing Jack’s old size 13 golf shoes, five sizes too big. “I just miss him,” I told her.

“You need to do something different,” she said patiently. “Go somewhere. Where would you like to go?”

I stared at the TV. “Right there.”

I don’t know where a man would go to become a race-car driver or a chef, but if you want to become a caddie, there’s only one place. And so, in the middle of February, I flew to Scotland and took up residence in the North Sea village of Elie a 40-minute bus ride southwest of Kingsbarns because there was a local golf course there with winter green fees I could afford. Carrying rocks in my bag to increase its weight, I played my way back into the game and into shape, walking 36 holes a day, always marching at a good clip and pacing off the yardages in my head.

“I’m in training!” I yelled to a grounds­keeper during a ten-day gale when the wind knocked me to my knees twice.

“You’re mad!” he yelled back.

Maybe he was right.

ON EASTER WEEKEND, I was finishing my second round in a snowstorm when the same groundskeeper gave me the name of the caddie master at Kingsbarns. I met Davey Gilchrist two days later, a lean and fiery Scotsman who sized me up while he listened to my story. “It’s an awful hole inside you after your kids leave,” he said when I finished. Then he looked right in my eyes as he shook my hand and said, “I can always use a hardworking caddie.”

I began as an unpaid “shadow,” walking beside a real caddie, a local lad named Ken, and paying him two pounds for the privilege of being his apprentice for a round. He draped his arm over my shoulder each time he helped me calculate the wind and the distance needed to carry hazards. On the greens, he crouched and surveyed the contours like a carpenter eyeing the warp in a board, then showed his golfer the best line to the hole. I watched and saw nothing.

“I feel like a blind man,” I told him a few holes later.

“Another 100 rounds and you’ll know this ground better than your backyard,” he said.

I finished my third shadow round at 2:30 one afternoon. I was walking back to the bus stop when one of the boys from the pro shop appeared in a golf cart with word that two golfers from California needed a caddie. All the others had gone for the day.

“I’m just a shadow,” I said. “But I would love the chance.”

I’d been on Oprah twice to talk about my books and remembered being pretty nervous, but not like I was that day. I began by forgetting the golfers’ names three seconds after the starter introduced them, then forgot the pin placements as well. Later, I dropped a putter cover into the fairway and didn’t notice for 200 yards. I won’t list all my mistakes, but if you’re wondering whether a caddie has ever handed a golfer his driver cover instead of his driver, the answer, sadly, is yes.

I felt like an imposter when I showed up for work the next morning. “I made a lot of mistakes, Davey,” I said.

“Aye, but you dinna make any new ones,” he said.

I tried to give him the money I’d been paid, but he wouldn’t take it.

“You’re not a shadow anymore,” he said.

AND SO I STAYED, and the days of April settled in. I was too nervous to eat breakfast before I left the small room I’d rented in Elie to catch the 5:58 a.m. bus to Kingsbarns. From the bus stop, it was a half-mile walk to the course, usually in the rain, which meant waiting for a job in wet clothes.

For a new caddie, there is always the waiting. I was behind 40 veterans, soft-spoken fellows who rolled their own cigarettes, refugees from the real world, where they had once been cops, teachers, chefs, and truck drivers. By now they had walked thousands of miles with golf bags over their shoulders, and as they were called up ahead of me, they sometimes called back, “See you out there, man.”

Often I waited until just after noon, six hours, before Davey would come out and say, “I have a job for you this afternoon. You’ll work today, Don. 3:10.” I would thank him and do the math: Three more hours of waiting, then five hours on the course, then an hour to get home a 15-hour day. The understanding was that you had to endure this patiently as part of your training, watching the veterans walk off to work and hoping you’d get your chance.

Those were the times when the longing for my family was brutal. I learned to pass the hours by playing the course inside my mind, silently picturing all the hazards and yardages. It took me 40 minutes to play a round. Then I’d switch the wind direction and play it again.

The pain of waiting always vanished the moment I headed down the fairway with a golfer beside me. When I helped a bloke from Ireland break 90 for the first time in his life, he gave me all the money in his pockets. A gentleman from Australia called me Tom, John, Bob, and even Roy for 15 holes, even though my name tag read don. But when I read the break perfectly on a long putt for birdie on 16, he ran into my arms as if I’d rescued him at sea.

By May the land was beginning to claim me. The dramatic elevation changes, the way the fairways swept along the sea all of it inhabited me now, and when I shaved in the morning I could picture every hole in my mind. That stunning physical beauty and the camaraderie among the caddies was what I looked forward to. Often, when I was the last man tending a pin, I would walk off the green to discover that one of the other caddies had carried my bag with his to the next tee.

Once, in a freezing-cold rain, one of the boys saw me shivering and peeled off his jacket to give me his dry sweater. I didn’t want to take it, but I was too cold to turn him down. Every time something like that happened, Glen Carter, a veteran Canadian caddie, would remind me, “You’re entering the fraternity now.” He understood the father-son part of what I was trying to do. He was grieving the death of his own father and had come out of retirement to walk off some of his pain.

I WAS THINKING OF GLEN on that September day as things got worse for my struggling golfer in the pink shirt. By the time we reached the sixth hole, a storm had blown in with sideways rain and 30-knot winds. We faced three more hours with numb hands and rain in our shoes. When he hooked his second shot on the par-five 12th onto the beach and glared at the dark sky, I remembered the first thing Glen had taught me: Let him give up on you, or even God, but never on himself.

My eyes were riveted to the spot where the ball had come down, and I was already marching straight for it when I heard him say, “What an idiot. All that fairway to the right and I put it in the ocean.”

I called to him as I walked away. “The tide’s been out all morning. If I find the ball on sand, we can play from there.”

I did, and he hit his 58-degree wedge from the beach, 48 yards, high over dune grass and a wretched bunker to a soft landing 40 feet short of the hole. He ran up to see the result. I was already handing him his putter when he turned and thanked me. “If you stood me in that spot for 50 years,” I told him, “I couldn’t have hit a better shot.”

He parred every hole from then on. When I watched him laughing with his buddies as they headed into the clubhouse, I felt the way we all feel after a good day’s work.

Five days later, I did my last loop in Scotland during the opening round of the Alfred Dunhill Links Championship. I rode the bus through the morning darkness, watching the slow parade of fishing boats as we passed through St. Monans and Pittenweem, thinking of Jimmy Hughes, who fished the North Sea for 41 years before he began caddying with me. Jimmy, whom I relied upon for weather forecasts and who became a great reader of putts.

At the gate to Kingsbarns, the big blue Dunhill signs waited for me. I was nervous at first but soon began fighting for each stroke alongside my golfer as we marched down the same fairways I had worked 140 times before. Only this time I shared them with Padraig Harrington and Paul Casey, the two pros my son admires most.

The moment I will always remember came as I walked off the sixth green and made my way through the gallery to the seventh tee. Glen stepped out of the crowd and shook my hand. He had taken a day off to watch me work my first professional tournament. We didn’t say anything, but when I looked into his eyes I knew he understood. I still had a long way to go to measure up to him and the veteran caddies I’d worked with all season. But I thought I just might get there.