I’ve had bigger caddie jobs. My players have won U.S. Opens and Players Championships. When it comes to high-stakes moments in a pro-caddie career, my round with a golf writer on a random Monday shouldn’t have registered.
Why was I so nervous before my round caddieing for Shane? It’s because I can always help tour players get more out of their game, but with a middle-handicap golfer like Shane, I sensed it wouldn’t be as easy. It’s one thing to hand a club and point to a target for one of the best players in the world but quite another to hand it to a guy who makes his living in front of a keyboard.
As Shane’s 91 at Deerwood Country Club that day proved, physical ability is only part of the challenge. Most average golfers don’t really know how to think their way through a round. In many ways, they’re the kind of players who need a veteran caddie most.
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This might sound obvious, but when you caddie for tour players, they know why they’re there. Every round they’re trying to shoot the lowest score possible, and outside of small disagreements, they’re trusting you to help them get there. Average golfers aren’t as certain. They say they want to shoot a low score, but if it means conceding their limitations—aiming away from flags, putting instead of chipping—they’ll resist more than they should. Some players also want that good story to tell at the bar afterward. There’s nothing wrong with that, but if Shane wanted to squeeze out his best score, I wasn’t looking for heroics.
For most of our round that day, Shane stayed on the right side of the excitement line. Compared to his practice round without me the day before, he scored five strokes better—and that’s with gusting wind and the added strain of a camera crew chronicling our every move. Sure, the end was messy—I’ll get to that in a bit—but even the end was tied to how well everything had been going to that point.
Lesson No. 2: Good confidence vs. dumb confidence
What was clear about Shane from the moment we met on the range is that he had some game. At times he hit the type of shots high-level golfers hit—tight draws around doglegs, chips that stopped inches from the hole. Other than the two-gloves thing—he said it was because of how much he sweats—he at least looked like someone who knew what he was doing.
The funny part is how often this can work against average golfers. The fact that they can hit certain shots is often confused with expecting they will on command. Only a small percentage of players can do that, and they’re the ones who pay my salary. For everyone else, the bad shots are the bigger part of the equation, and with Shane, I recognized I needed to walk a unique tightrope: I wanted him to believe in himself but not so much that he would do something stupid.
Lesson No. 3: It only takes one swing 
Webb Simpson is helped out of a bunker by his caddie Paul Tesori on the 18th hole during the third round of the 147th Open Championship at Carnoustie Golf Club.
Harry How
Playing smart isn’t everything, though. The wind was howling. We turned in 48, and our energy was sagging. Shane felt like he was underperforming, and I worried I wasn’t holding up my end, either.
However, if there’s another place where a caddie can earn his money, it’s in propping up players when they need it. Very little had gone right the last few holes, but I also knew it wouldn’t take much to give us a jolt. This is another tightrope caddies walk. Our job is to keep our players’ positive, but we still need to meet them where they are. Shane had a right to be bummed. The phrase I use with my players is, “Head down, chest up.” It means you can take a moment to be ticked off, but you can’t slump your shoulders so much that you feel defeated. Standing on the 10th, I reminded Shane he was one swing away from turning things around. When he piped his drive over the water and into the fairway, it appeared he had.
Lesson No. 4: Ride the wave
Golfers can change over the course of a round. I’ve seen it happen countless times, and even with Shane. He had a new swagger on the back nine and ended up giving himself a series of birdie looks as a result. Even when he didn’t, he handled challenges with greater ease. On the par-5 13th, I pointed him well left of the fairway and told him to try to cut the dogleg. He executed it almost to perfection, tapping in for par. Earlier in the day we said we wanted to break 90, only to put it to the side after the rocky start. Now Shane just needed par on the par-5 18th for 89. At the time, it seemed simple enough.
Lesson No. 5: Stay grounded in reality
When you talk about hoping for the best versus preparing for the worst, 18 was an unfortunate reminder. On the tee, I gave Shane a line left of the serious trouble. In hindsight, it wasn’t left enough. When Shane blocked his tee shot right and out-of-bounds, I shook my head. “You got golfed,” I said. We both did, really. The double for 91 left a bitter taste given the way Shane and I were rolling right before that. I was disappointed for Shane. More surprising is that I was disappointed for myself. There wasn’t a big paycheck or Ryder Cup points on the line, but there had been the same competitive rush and now the same hollow feeling after falling short. Just like caddieing in a major, I went through a checklist of things I felt I did well and a few I might have done differently. I know Shane meant it when he said I really helped him, and I would love another chance. Caddieing on tour is what pays the bills, but it’s not the only place I can make a difference.
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This article was originally published on golfdigest.com
