Against the Wind

I am standing in a pit of sand, pushing dirt around, back and forth, back and forth. The wind is howling right through me, driving the falling rain against my glasses, ensuring each drop’s descent is more horizontal than vertical. My lower back grabs with every movement, my cheeks are flush from the chill, and my feet are on the verge of incineration; you would’ve thought I’d taken The Proclaimers’ one-hit-wonder literally and walked 500 miles—then walked 500 more. I am 35-years-old doing the job of someone 20 years younger. I am doing it voluntarily, and I am doing it for free.

I am a caddy-in-training at Bandon Dunes.

Nobody said changing your life would be easy, and I’m certainly finding that to be true a couple weeks into this journey. Much to my surprise, though, it hasn’t been my anxiety’s greatest hits—money, writing, what happens next—that have given me the most trouble; it’s been the little things, the stuff I glossed over and dismissed as no big deal before all of this started.

Such was the case with caddy training. Obviously, I knew I’d have to go through some sort of educational process; they weren’t just going to throw me out on the first tee with the Dalai Lama himself. But on paper, the training didn’t appear to be all that demanding; basically, you just follow, or “shadow,” experienced caddies while they work. This gives you the opportunity to both see how the job is done correctly and to begin familiarizing yourself with the golf courses. Bandon Dunes has four 18-hole layouts, and you are required to shadow two rounds on each, for a total of eight rounds.

My goal was to approach the training as aggressively as possible, to get it over and done with in four or five days. This would not only allow me to start making money as a real, live caddy quicker, but it would help me feel a little more settled in what, to this point, remains an unnervingly foreign environment. I needed to begin building a new comfort zone and all that that entails—developing a daily routine, learning the job, maybe making some new friends—and my hope was that the training could be a viable first step.

It didn’t take long to realize, though, that as far as first steps go, this was going to be a big one.

For starters, lesson No. 1 in caddy training doesn’t have anything to do with where to stand or how to carry the bag; it’s all about status, in that, as a trainee, you have none. You’re a private, a pledge, a conditional Tri Lamb trying to earn a charter. You know nothing, you have nothing, and you get nothing. Everyone else is geared up in cool looking, logoed uniforms; you wear your own clothes with a green bib over them that has “Trainee” in bright, white lettering across the back, broadcasting to the world exactly who you are and where you stand. If we’re getting technical, the bib should probably read “I’m with stupid.” That would be much more on the nose.

Complicating matters, at 35, I was not your typical trainee, meaning I had no natural peer group. The other trainees were young—like, “Mom dropped me off at the course” young—which I’m not; the older guys were experienced, which I wasn’t, either. This left me squarely in No Man’s Land (and I thought I’d already driven through that in Wyoming), sitting in the corner of the caddy shack, my face buried in my phone in hopes of giving off the appearance that I wasn’t as lost and alone as I actually was.

My insecurities only increased once my shadow rounds began. Shadowing is a lot like “following” in restaurant training—and just as awkward. Even in the open space of a golf course, there’s not really room for you. There are the players, there are the caddies—and then there’s you. You’re just kind of there, infringing on the natural order of things, making it all feel a little more cramped and congested.

As uncomfortable as it was, though, I was determined to force my way into the picture each time out, eager to do a good job and prove my worth to the experienced caddies I was shadowing. Caddies can be an interesting breed, and the ones I was paired with were of all different ages and backgrounds (though none, unfortunately, possessed any of the sweet nicknames I’d overheard in the caddy shack, like Minnesota, Rodeo, or C-note). But generally speaking, no matter who it was, they could each be cast in the role of one of three types of “Guys.”

The first type was Indifferent Guy. These caddies were perfectly nice, and they even spoke to me a bit throughout the round. They were there to do a job, though, and it didn’t really matter to them one way or another if I was there or not. But since I was, they figured they might as well use me, and all that they asked was that I lend the occasional hand and make their lives a little easier—at no cost to their bottom line, of course.

Their wish was my command, though, and I pulled every flagstick and waded into the weeds to search for errant shots whenever they asked, and I did it without hesitation. I told myself it was because I was a hard worker, and that I was just doing what I was supposed to do. But in the spirit of full disclosure, beneath all of that enthusiasm was a desperation for approval, an inherent need to feel liked and accepted. My pitiful, pathetic rationale was that if I just raked these guys’ bunkers (that’s not a euphemism, I swear), then maybe they’d want to be my friend.

Day 2 of my training brought me a looper from the second category—Instructive Guy. Even before I had a chance to start slacking, he told me to get ready to work, that he expects his shadows to carry bags, check yardages, and be involved with the entire group. My initial thought upon hearing this was decidedly Arnold Drummond in nature. Don’t get me wrong, the desperation to be liked was just as strong, but I also didn’t want to be taken advantage of, and I wasn’t too keen on the idea of running around and servicing all of the players (again, not a euphemism)—only to have the players pay somebody else on the 18th green.

And sure enough, from the moment we stepped onto the course, he put me to work. But he also did something else—he trained me, giving me tips on aiming lines and wind direction and club selection, stuff I’d be able to use once I started caddying for real. We were only together for one round, so I can’t say our relationship reached Daniel-son/Mr. Miyagi levels (plus, I didn’t sand his deck or paint his fence, and he didn’t give me a vintage, yellow car that would make a young Elisabeth Shue swoon), but his interest in me appeared genuine, which in turn helped me feel accepted and more at home. There’s a subtle yet distinct difference between being nice and being welcoming, and this guy was welcoming—and not just because he gave me my first measure of income that may or may not be reported to the state of Oregon.

It wasn’t until my final day of training that I met the caddy I’d honestly been expecting to meet all along—In The Name Of All That Is Holy, Stay The Eff Out Of My Way Guy, or ITNOATIHSTEOOMWG for short.

For as shy as I can be at times, I’ve actually been assertive in trying to defuse the awkwardness of shadowing by immediately introducing myself to the caddies in the group and letting them know I’m there to help in any way I can. In most instances, this is a pretty straightforward task. It’s a standard social situation, after all; you both kind of look at each other, and that opens the door for introductions and pleasantries.

But with this guy, even a split second of eye contact was apparently too much to ask for.  

Because the resort is so spread out, there are buses that shuttle caddies from the shack to the various courses on property. As I took my seat directly across from him, I instantly started looking—literally, at him—for an opportunity to say something. Nothing. After a few minutes of being completely ignored, I resorted to staring at him like some soon-to-be-featured-on-20-20 serial killer; if this were a city bus, the person in his seat would have undoubtedly been yanking the bell as if they were playing a slot machine. And yet, he remained unfazed and unaware. Once we got to the course, it was a few minutes of killing time outside the pro shop, waiting for the guests to arrive. Still nothing. Then, we walk up to where the starter was (the person you check in with before teeing off), and the guy turns into Chris Rock, firing off one-liners and cracking the starter up—all while I’m standing there like an idiot, laughing at his jokes, hoping that it might get him to look in my direction. No dice. Finally, we’re on the first tee, and I strategically stand right next to him. This was now-or-never time. I turned and introduced myself, not really knowing if I was going to get any level of reaction. Mercifully, this form of communication was so direct that not even he could ignore it, and he obligingly/begrudgingly shook my hand. Victory, at last.

Then he proceeded to not acknowledge my existence again for the next four hours.

Actually, that’s not entirely accurate. On the first hole, one of his players hit into a bunker, and I ran ahead and grabbed the rake to take care of it for him. Before I knew it, he had sidled up next to me and—without words or eye contact, of course—started motioning for me to give him the rake. Clearly, he didn’t want me doing a thing for him or his guys, the assumption being that, in his mind at least, this could potentially be taking money out of his pocket. If I were to assist, would the guests feel like they had to pay me something? Would they think that because he didn’t do as much, they could then pay him less?

For the record, I totally respect this mindset. Caddies are independent contractors, paid directly by their players, and as far as I know, he wasn’t getting a dime extra from the resort for letting me tag along. I don’t even think he had a say on whether I was assigned to him or not. His focus was solely on doing the best job that he could, so he could make as much cash as he could, and rightfully so.

Still, there’s got to be a nicer, less childish way to go about getting that message across. Had he looked at me before the round and said, “Hey, don’t worry about doing anything for me or my guests, I’ve got it covered,” that would’ve been that. I wouldn’t have gone near a bunker or flagstick all day. Instead, I was left to feel like even more of an outsider than I already was. How people ever forget where they came from, how it slips their mind that they themselves were once the pledge or private, is beyond me. But that appears to just be an unfortunate part of human nature.

At least I still had golf, though. I might not have had any friends, and I might have resorted to eating lunch in my car to hide that fact, but if there was one aspect of the job in which I would be at ease, and if there was one place where I’d always feel at home, it was out on the golf course.

Or was it?

Bandon Dunes is like no other golf destination in America, mainly because the courses here are true links courses—meaning they’re natural and out in the open. They’re built on rolling terrain through the sand dunes, and they’re completely exposed to the elements. It’s the way courses were originally designed in Scotland (see: St. Andrews), and it gives people the opportunity to experience this old-school style stateside—without having to subject themselves to haggis after their round is over. As the resort’s mission statement explains, it’s golf as it was meant to be.

It’s also golf with which I am completely unfamiliar.

Whereas American-style courses, the courses I grew up playing, are reliably straightforward—there’s the fairway, there’s the green—the courses here are decidedly complex. There aren’t trees framing every hole, and there aren’t any rich people’s back yards to use as a guide to tell you where and where not to hit it. And, because everybody walks, there aren’t even cart paths you can follow to find the next tee. At first blush, the entire layout looks nearly identical; all the holes run together in your mind, and it’s difficult to decipher from memory what is what.

And the wind. My G-d, the wind. I’m from Texas, where it’s known to blow a knot or two, but I’ve never seen anything like this. Heavy, blustery, relentless. And considering there’s nothing to block, deflect, or redirect it, you feel its full force; a 20 mph breeze is an unfiltered, tighten-your-hat-strap 20 mph. During one of my shadow rounds, I’d struck up a conversation with a player in the group, and on one hole, he thought it’d be fun to test my knowledge and asked how far I thought his shot was playing. I looked at where he was, factored in the headwind he was going directly against, then gave him a yardage number.

Then his actual caddy stepped in and corrected me, trumping me by 35 yards.

Thirty-five yards. I’d misjudged the wind by 35 freakin’ yards. For the non-golfers out there, that’s a ton. In baseball, it’s the difference between a routine pop-up to shallow left and a homerun down the line. In fantasy football, it’s the difference between a PAT (one point) and a 55-yard field goal (five points). In basketball, there is no equivalent, because the court isn’t even 35 yards long.

And in caddying, it’s the difference between getting paid and getting told, “Gunga galunga.”

(I’m aware that I’ve made two references in this article alone to the same clip, but what are you going to do? It’s the greatest (only?) caddy monologue of all time. Actually, the name of the blog itself makes it three.)

The bottom line is that, when it comes to links golf, a good caddy is absolutely critical. It requires so much more strategy and so much more local knowledge, and even after walking the courses a couple of times, I didn’t know or have any of it. Shortly, there’d be a player depending on me to effectively get him from tee to green, yet I wasn’t even sure I’d be able to get him from the green to the next tee.

There was also concern that I wasn’t strong enough to make it to the next tee myself. I’ve always thought I was in half-decent shape (minus my chicken legs), but I had no idea of the toll that caddying would exact on my body. And a quick glance around the caddy yard on my first day didn’t make me think any differently. There weren’t any stone-cold specimens or workout warriors walking around; there were a bunch of guys with big guts and even bigger breakfast burritos on their plates. Besides, I’d survived the maniacal P90X home fitness program not all that long ago. If I could do that, surely I could do this. 

Talk about rude awakenings. It took all of one round for me to start singing, “Where have you gone, Tony Horton, my aching body turns its lonely eyes to you.”

The training was a total of 144 golf holes (eight 18-hole rounds), and after just 18, I was tired—and a little embarrassed by it. After 54, I was as drained as I ever was during P90X. And by the time I finished 72, it hurt so badly to stand up, I was tempted to join my items on the conveyor belt while I waited in line at Walmart.

And I wasn’t even carrying anything; I was just walking.

In hindsight, this probably shouldn’t have come as a surprise, considering that up until a couple of weeks ago, I’d been spending approximately 93.7% of my time either sitting at a desk or on a couch. A long walk was a walk to my car—at which point I’d then drive to Chik-fil-a for some chicken nuggets. Now, I was walking all day, with virtually no break, up and down hills and over sand dunes. And, because the closest Chick-fil-a is in California, I’ve had to stay on my feet a little longer every night to make something to eat.

The worst pain was unquestionably in my feet. Late in the afternoon one day, I could literally feel tears forming way in the backs of my tear ducts. My feet hurt that badly. It didn’t help that, beyond the agony, I had little else on which to focus, because I wasn’t really doing anything. I wasn’t giving yardages or reading putts; I was just in my own world of hurt, trying to direct my attention anywhere but here. And once that mindset kicks in, it becomes that whole “Think of anything but…” sort of thing.

What’s ironic is that I probably have the most technically advanced shoes of any caddy out here. The company I left to come do this sold high-end sporting apparel, from brands that are so expensive you’ve never heard of them, and I’d gotten the shoes through them (for free). This was first-class, top-of-the-line footwear, built for crazy athletes who find joy in rigorous mountain runs and 100-mile races. And yet, here I was, writhing in pain from walking. So just for fun, I went back to the website and read the description of the shoes—a description that I had written—and it went on and on about their unrivaled cushioning and support, about how when you’re wearing this product, you feel as if you’re flying like a gazelle.

Meanwhile, I could hardly stand long enough to make a bowl of spaghetti for dinner.  

So here I am—bruised, battered, and barely upright. And thankfully, now finished with caddy training. I knew before heading west that this whole thing was a massive undertaking; moving across the country, taking on a new job, committing myself to writing, gunning for a cool caddy nickname…it was a lot to take on. And every time I foolishly dared to look at the big picture, it was always too overwhelming to comprehend and had me contemplating going fetal. So for the sake of my sanity, the only way I could approach this was to do so incrementally, to just focus on whatever was immediately in front of me, and leave the down-the-line concerns for down the line.

And really, it’s in the small stuff where progress lies—stacking one little victory on top of another, steadily checking off item after item from your to-do list. So that’s what I’ve tried to do from the very beginning:

Get in my car in D.C. and start the ignition? Check. Make it beyond the first exit without getting off and turning around? Check. Overcome fear of eating a sandwich from a Subway that’s attached to a gas station called Kum & Go? Check. Remain fully conscious while driving across the desolate landscape of Nebraska? Check. Figure out where Walmart is, because the Safeway didn’t sell Peter Pan, the unquestioned king of the peanut butter pyramid? Check. Clean off my George Foreman Grill, so I can make tasteless chicken breasts and hamburger patties for dinner every night? Check. Break the habit of getting out of my car when I need to fill up, because Oregon is a “Full service”-only state? Check. Update my Slingbox software, so that my girlfriend and I can have Skype dates to watch “Dexter” and “The Bachelorette” together? Check. Trade in the embarrassing green “Trainee” bib for a sleek, logoed black rain suit and classy white coveralls? Check. Make eye contact with the caddy who ignored me during my shadow round, because I’m now an actual caddy and no longer a threat to the money in his pocket or to his very way of life?

Okay, so nine out of 10 ain’t bad.