I spent a good three months worrying about all the possible disasters that could derail this experiment, including versions of the one that happened. Some days I preemptively cursed the editors who dreamed up the concept: How can a professional caddie help an average player like me, a guy who has broken 80 once in his life? I worried that I would disappoint Paul Tesori, the caddie fool enough to waste his time with me. I worried that, legend or not, he couldn’t do anything for me short of swinging the club—and there were times when I wish he could have.

The one thing Tesori and I shared, which would prove to be an asset, was a love for competition. It’s true that as a former member of the University of Florida’s 1993 national championship team and a major-winning caddie (his roster of players includes Vijay Singh, Webb Simpson and, now, Tom Kim), he’s just slightly more accomplished than an overweight 41-year-old writer, but it’s still a bond. It meant that even at the lowest ebb, he and I had something to chase.

The day before, I played Deerwood Country Club in Jacksonville without Tesori. It’s a classical water-logged Florida course with a Course Rating of 70.1 and a Slope Rating of 135 from the 6,259-yard white tees we played, lovely to behold but perilous to play. Tesori said later it was more difficult for someone like me at a distance of just over 6,000 yards than TPC Sawgrass would have been; maybe he was just being nice. I shot a 96 in windy conditions, and by the back nine I was psychologically battered by the gusts and the endless godforsaken water. Based on that result, Tesori thought we could shoot 89 the next day. It became his mission.

Private Deerwood Country Club Jacksonville, FL

“A classical water-logged Florida course with a Course Rating of 70.1 and a Slope Rating of 135 from the 6,259-yard white tees we played, lovely to behold but perilous to play.”

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WITH TESORI AS MY SHERPA, I CHANNELED AN ABILITY LEVEL THAT HAD VANISHED DURING THE WINTER AND SPRING. I GOT HOT.

I was the doubter. I had never played with cameras on me or with a drone buzzing overhead, and when the day came, both water and wind had returned for an unwanted curtain call. In my deepest heart, I didn’t believe 89 was in the cards, and a 48 on the front seemed to prove me right. At the turn, I stood imagining how bad things would get in the next two hours.

Then something odd happened: With Tesori as my overqualified sherpa, I channeled an ability level that had vanished during the winter and spring. I got hot. By the time we reached 18, I needed a par for 89. Tesori was buzzing. I was buzzing. I asked him on camera how I could avoid a choke, but in my heart I felt confident. This was a short-ish par 5 and an easy one; even during the disastrous late meltdown the day before, I had made par without breaking a sweat. Tesori reminded me to move my chest on the backswing. I stepped up, I swung . . .

We’ll get there.

LINE OF ATTACK PGA Tour caddie Paul Tesori (far left) and Shane Ryan talk strategy.

First I want to tell you that Paul Tesori is a genius—and not just as a caddie. He has this strange habit of reading your mind, especially when the mind has failed, but he does it in the nicest way possible, charismatic and funny, with a lively Florida drawl.

“Did the water get in your head there, or were you pretty good?” he asked me after a blown 5-wood, knowing full well the water had gotten in my head. By deferring to me, though, he let the conversation progress without blame and made the ensuing lesson easier to swallow.

“You’re too good to hit that shot,” he said. “I think that’s where you have to judge yourself. Like, come on, if I hit a bad shot, I hit a bad shot, but I’m not going to hit one because I’m scared.”

I liked him instantly, and I think he liked me, but even if he didn’t like me, he made me think he did, which seems like an important skill for his job. Before we got into the nuts and bolts of how to approach the round, he took an average golfer about to play a tough track in front of an entire film crew and put him at ease. When I stunk that day, it was because I’m not very good; when I was great, I was great because of him.

I could list two dozen examples, but my mind keeps returning to the fifth hole. To that point, I had made four bogeys, each because of a small miracle—two divine chips, followed by a downhill curling seven-footer that trickled into the cup after a perfect read from Tesori—but now I was staring down a hole I hated, a par 4 into a ridiculous wind, water along the right the entire way, and a peninsula green surrounded by more water. It was nightmarish, and a day earlier I had put myself out of my misery early by hitting my tee shot into the water.

But now, coming off the invigorating putt, I smashed a driver on the perfect line and left myself 126 yards. There, facing 20-mile-per-hour gusts, I had that sixth sense that bad golfers get, the one where I knew, deep in my bones, I was about to embarrass myself.

Tesori had my back. His first piece of advice was broad—aim right, as in, way right. Forget the middle pin and the “pretty white flag.” Aim at the palmetto tree that is even right of the edge of the green. Why? Because when you’re trying to maximize a score, conservative strategy plays, and aim matters. A player like me needs to give himself room for error, especially when there’s a punitive result like water in the mix.

His second piece of advice was to use a 6-iron. On a bad day, my 6-iron still flies 160 to 165. To use it here, with 126 yards to go, seemed insane even with the wind, but he insisted, and I complied: 6-iron, aimed at the palmetto right of the green. I flushed it. I also did the exact thing I knew I couldn’t do, which was to pull it way the hell left.

“Somehow be the right club!” Tesori yelled into the wind. “Somehow!”

Somehow, it was. The ball landed on the thin slice of peninsula protruding into the ghastly rippled blue: green in regulation. We reacted like we had just won the Masters, relief and joy coursing through us, but Tesori had a point to make. “There’s the pin,” he said, pointing. “Our target was 35 feet right of the hole at that palmetto patch. Look where our ball is. If we were aiming at the pin, it’s in the water every time, and we’re dropping here, and you’re probably making 7, versus if we hit at the palmetto patch, we’re going to make 4, and if you pull it where you did, we’ve got two putts for 4.”

EBB AND FLOW At the turn, Ryan imagined how bad things might get in the next two hours.

It occurred to me then that without Tesori, I would have aimed at the flag and used an 8-iron, which meant I was certain to hit the water two different ways. Instead, we were alive. As we walked away, I marveled at my divot, which pointed exactly where the ball had gone, even though I aimed far to the right. “That’s just a little bit of a lack of talent,” he said, his voice as upbeat as ever.

THE MOMENT WAS MIND-EXPANDING AND WILL CHANGE HOW I APPROACH THE GAME: WHEN TO PUSH AND WHEN TO RETREAT.

That lack of talent, which we had hidden until that point with Tesori’s guidance and some atypical short-game magic, now emerged in its full glory. A series of doubles ensued; by the turn, my 48 put me on course to match yesterday’s 96. It was our darkest hour. I sat on the back of a cart and stewed while the crew changed their batteries and hydrated. I felt tired. I told my editor that we might be on the verge of a true disaster. I badly needed a pep talk, and there was only one man who could provide it. “No. 1,” Tesori said, “how many times do you sit at home and want to play 18 holes? Happens all the time. You don’t get that many chances. First of all, I would just say, jump back to reality: I get to play 18 holes today for free.”

“You and I were literally fist-bumping and celebrating an hour ago. Now both of us, our demeanors are a little down, our voices aren’t as high as they were, not as many pumped fists. I think the biggest thing is, let’s hit one good shot and get a little bit of momentum.”

I hit a decent shot, a drive over an intimidating expanse of water. Then I hit a great shot—a 4-hybrid to a hidden green, the ball coming to rest 10 feet away. Finally, finally, I made a par. Just like that, we were rolling. Everything felt better, and we came into the par-5 13th with momentum. The layout of the hole suggested two paths. First, the traditional dogleg left route, hitting wide right to a fairway bordered by water. Second, you could get creative and use the 14th fairway to the left. Tesori had a third path in mind: directly at the trees ahead, into the woods, pretty much straight at the hole. How? The answer, as he explained, is that what looked like a wild risk was the smartest play. If I could elevate over the line of trees 50 yards ahead of me—they weren’t tall—the ball might not reach the fairway in the distance, but it would inevitably reach a clearing past the woods that gave me a water-free look at the hole.

It’s hard to explain how impossible this was to envision standing on the tee, but I trusted Paul’s intuition. I hit a drive that was solid but low (of course), but it still managed to get over the trees, ticking a few leaves along the way, and it crawled up to that clearing. Now I had a 5-wood in between a pair of trees—a space just wide enough for me to pass through and find the rough pin high. Next, a so-so pitch, a missed 12-footer, and a tap-in par. That hole is forever burned in my mind because I genuinely did not hit one shot I’d call “good,” and it was my easiest par of the day, all because Tesori charted a path that didn’t seem to exist.

No hyperbole: The moment was mind-expanding. It will fundamentally change how I approach the game. In microcosm, it happened again and again all day: when to play safe, when it’s safer to take a risk, where to aim to minimize damage, when to push and when to retreat. (On one hole, after I drove my ball into the woods, he offered me the chance to consider a risky shot through the trees; when I hesitated long enough at the prospect, he said, “There’s your answer,” and made me punch out.) He wasn’t infallible—we disagreed on a few green reads, and though I was mostly wrong, I was not always wrong—but his wisdom buoyed me at every step.

I DID NOT HIT ONE SHOT I’D CALL GOOD, AND IT WAS MY EASIEST PAR ALL BECAUSE TESORI CHARTED A PATH THAT DIDN’T SEEM TO EXIST.

Then came the 18th tee. Just an easy par, on an easy hole, and I would have the 89 and a triumphant ending to my story. But does golf ever oblige? Of course not. I drilled it way right, absurdly right, tragically right—a total block plus fade plus a kiss from the blackhearted devil himself. I was mainlining pure misery the second it left my club. “It’s going to be fine, isn’t it?” I asked, as though a simple word from Tesori could alter reality. The ball traced an arc through the trees, on a path to somebody’s front yard. He did not think it would be fine. We waited to hear what happened via radio, and the news broke us both: out-of-bounds by two feet.

The dream was dead. I won’t call it the biggest shot of my life—that came on the day when I broke 80 (home course, no wind, better game)—but considering the circumstances, it was big enough. Tesori was despondent and couldn’t hide it. God help him, this man who spends his life working with athletes of actual ability had believed in me.

POSITIVE INFLUENCE Tesori’s pep talks in low moments were as valuable as his tactical advice.

Then, in the thick of all that self-pity, I heard a strange sound: applause. A few yards to our right, three kids holding little plastic clubs were watching from their front yard. All they saw was some guy being followed by a film crew—presumably a great golfer because why else would anyone care? Being sweet kids, unaware of the circumstances, they clapped, which means that one of the lowest moments of my entire golf life is also the only time I’ve ever been applauded by a gallery.

Even with a gag at the finale, all those months of worry were wasted. Tesori made it impossible not to enjoy the day, and my only regret is that for all the knowledge he imparted, the one thing I can’t take with me is his actual presence. The day-long lesson in tactics will change how I play the game, but the psychology—particularly in the brutal low moments at the turn when he gave me the sorely needed kick in the pants—will change how I feel about the sport. The nature of certain brains is to take even games we’re not very good at far too seriously, and that’s fine because to live a complete life we have to care about something beyond the really big stuff. When the despair hits, as it will, we can always buck up, we can always carry on. We can reach the dawn on the other side of darkness, and we can achieve that heady golfer’s dream of giving ourselves a precious chance to choke.

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