The best caddying of the year is in September and October, when the younger kids have gone back to school, when the golfers are more relaxed and grateful and willing to tip more generously, and when the weather rotates back and forth from warm and sunny to cool and cloudy.

The myth of fall caddying is that you can earn $1000 a week until the first Tuesday of November when the greens are aerated.

“A grand a week” is an idea that tortures those caddies who are stuck inside classrooms and libraries on spectacular autumn days—the kind of days that can only be properly experienced outdoors, while wearing a wool sweater, while striding around purposefully as brown old leaves twirl to the ground and define by contrast one’s own vigorous usefulness. They’re the kind of beautifully blustery days that provoke a craving for a well-earned and warm bowl of stew, chili, or macaroni and cheese.

“A grand a week,” is also an idea that seduces many veteran caddies to return to the suburbs for a couple of months in order to help finance the various things they’re trying only somewhat successfully to do as adults.

These fall caddies are ski bums in the Rockies and English teachers in East Asia. They are minor league baseball players, semi-pro golfers, fledgling writers, and aspiring musicians.

Some of the fall caddies are not doing much of anything and instead just vaguely and ominously “taking some time off” from college, from grad school, or from their previous and almost always disheartening corporate jobs.

For all these caddies, the daily spiritual challenge is to keep believing that this return to their parents’ house and to hauling golf clubs is just a temporary regression, and that they will soon move far enough ahead in life to not have to keep coming home again.

However, there are those men who do not stop caddying, or who tried to quit but then returned, permanently, becoming the “lifers” that spend, like birds or butterflies, their summers in the North and their winters in the South.

Many lifers tell a similar story when asked how they became full-time caddies. The stories could be cynically referred to as, “Variations on a Theme of Resignation.”

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Dave Hart is a lifer caddie who is in his mid-thirties and who comes back to Chicago and to our caddieshack each year after Labor Day. His parents live near the golf course and he stays with them while in town. He then works in either Florida or South Carolina for the winter and spring, and then Scotland for the summer.

When asked for his story, he usually begins, “I was in medical school in New York. I got engaged to a great girl. I was the pianist in a jazz trio and we played clubs in Manhattan.”

Dave often pauses his story there and sips his morning coffee or walks over to the heater in the corner of the shack to warm his hands.

“I started to get depressed. I was taking some drugs, but it wasn’t the drugs. I found myself listening to Pet Sounds a lot. I kept listening to this Neil Young song, “One of These Days,” over and over again and just getting extremely weepy.

“A good friend of mine, who I would describe as a tortured Catholic, told me to read Ecclesiastes, which I hadn’t read before.

“I read Ecclesiastes, and after that I just couldn’t care anymore. I couldn’t care about anything. Within a year I left medical school, I broke up with my girlfriend, and I left New York.

“I traveled for a while. I taught English in a couple of different places, but then I was in Europe and I went up to Scotland and felt like caddying again. I got a job looping at St. Andrews, then I started coming back here, and then because of some guys here I got connected to some courses down South.”

Dave tells this story as if he’s recalling from memory the deposition of a stranger.

Some caddies like Dave’s detached and quiet manner, and they look up to him as a model of how to lead a thrifty and simple life. Other caddies are offended by him and speak poorly of him, as if his apparent lack of desires was a threat to and a rejection of their own.

The caddies who do not like him call him a burnout, a bum, and a loser. They love to point out how Dave now occasionally has to caddie for Mr. Becker, a junior member who once caddied alongside Dave while they were both in high school in the early 1990s.

However, if you watch when Dave carries Mr. Becker’s bag, they each seem pretty happy to be around one another and to be in the presence of a childhood friend.

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As September passes into October, a group of ten or fifteen guys (and maybe one or two girls) keep showing up and become the de facto group of fall caddies.

Some of them leave before the season ends if they get a new job or if they become burned out from carrying doubles so often.

Everybody starts wearing gloves and hats and even the fair-skinned Irish caddies stop putting on sunscreen. Morning frost means the first groups don’t go off until 8:30, then 9:00 AM, and the shorter days stop play at 6:30, then 6:00 PM.

By late October, Clam the caddiemaster allows us to call-in from home in the mornings to let him know if we’re available to caddie that day.

Many of the members leave town for their vacation homes in the Southeast or the Southwest and the number of groups playing each day dwindles to four, three, two or one.

The fall caddies hang out together at night at the Irish pub or in somebody’s parents’ backyard for a bonfire. Some of the caddies lavishly spend the great quantities of cash they have at clubs and bars in Chicago.

Dave Hart comes to hang out sometimes, too. He arrives on his father’s old Schwinn bicycle and has a drink or two, a cigarette or two, and then rides back home.

One night, it was a caddie’s birthday and Dave had already had a couple of drinks when several shots of whiskey and more rounds of beer were passed around for everyone.

A cover band had been playing in the corner of the bar. After they were finished and once we were all thoroughly drunk, Dave was egged on to go play the keyboard and sing a song.

He sat down at the keys, adjusted the microphone, and sang a version of “I Just Wasn’t Made For These Times.” The suburbanites at the bar stopped, listened, and applauded when he was done.

Dave stood up with a beer in hand, took a bow, and said, “Vanity of vanities, my friends, vanity of vanities.” He then walked outside to smoke a cigarette. A pretty woman who looked a few years older than him got up from the bar, followed Dave outside, and began talking to him.

We gathered at the window to watch what was happening. We went out there to smoke cigarettes of our own and eavesdrop.

Dave and the woman walked back in and sat down together in a booth. They ordered several drinks and then left the bar at the same time.

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When the Fall caddies sit around the shack in the afternoons, all of them except Dave frequently check their phones for text messages and emails, as if with the approach of winter they’re more eagerly waiting for some sort of ticket that will let them proceed ahead in life and take them closer to those variously shining, golden things around which everyone’s lives are rotating.

Dave, however, usually seems very peacefully liberated from the rhythm of rewards and disappointments that arrive to a person each day via a digital inbox.

The day after that sloppy night at the pub, Dave asked to check his email on Ron Surlas’ phone.

“I thought you rejected all these miracles of modern living, Dave?” Surly asked him as he handed over the phone.

“Generally, yes,” Dave replied, as he fumbled with the touch screen.

“So did you take her back to your parents’ house?” Surly asked him.

“You know, believe it or not, she lives with her mother, actually. But we made do.”

Once Dave was done with the phone I asked Surly if I could use it to check my email.

I too was anxious to check my inbox, not for any particular reason, but just out of an obscure, daily desire to see if maybe that morning I would get the email that would be the summons to move to the city and participate in a culture and do meaningful things amongst interesting people, that would let me say of myself, “I used to be a caddie, but now I’m a ____ .”

There was no such email.

Maybe it was a terrible mistake to be waiting around and saving up money for that moment. Maybe if I wanted to be able to refer to my caddying in the past tense, then I just needed to get up, right then, and to go, to go somewhere more exciting and more dangerous.

To go before the winter came. To go before my desires weakened and withered. To go before I became any more dependent on the simple, repeatable pleasures of suburbia.

Maybe what I needed was to just walk out of the caddieshack, and to go, to go, to go.