The rules of caddying are simple: “show up, keep up, shut up, and don’t lose a ball.”


When I was 14, I begged my parents to buy me a new set of golf clubs. Tiger Woods had just completed the Tiger Slam and golf was “cool” for kids my age. My plan was to try out for the high school golf team, but I didn’t want to play with the cheap set of Wal-Mart clubs I got for my birthday a few years prior. After all, I wanted to be just as good as Tiger.

Until that point all I needed to do was ask my parents for something and they would usually buy it if the price was within reason. Sensing this as the perfect opportunity to teach me an important lesson about personal finance they told me to get a job. The set of Titleist clubs I was drooling over cost $2,500. If I wanted them badly enough, I had to work hard and save. 

For a high school student, caddying offered an opportunity to be around the game while making good money. My parents saw it as a way for me to be out of the house, get some exercise, and network with successful people. We found Rolling Green Country Club, a club near our house, and I applied. 

My dad drove me to the club six days a week during that first summer so I could be there by 5:30 am to put my name badge in the draw bucket. The draw is where the caddie master randomly selects your name to determine the order for loops. Some days you’re lucky and can start caddying right away, while other days your name ends up at the end of the list and you sit around waiting. Not caddying means not making any money that day.

Your senses awake before you do that early in the morning. There’s the distinct smell to the fresh-cut grass, the gasoline from the mowers, and cigar smoke. There’s the dew in the grass and the stillness of the morning before the sun rises. The sound of golf clubs clunking and banging together as the bag room attendant drives them up to the driving range or first tee. 

Lesson 1: Life isn’t fair

Kids whose parents were members at the club always seemed to get priority on the list no matter which way the draw unfolded. Either their parents or their parents’ friends would request to have them as caddies, pushing those who weren’t connected further down the list. I spent a fair amount of that summer sitting around waiting, but I took what I could get and worked my butt off when given the chance.

After a week of little action I was called into the caddie master’s office. “Here,” she said, giving me a ticket. “Mr. and Mrs. Snodgrass are going off the first tee in a few minutes.” The Snodgrasses were probably in their 80s. They were the stereotypical older couple who had belonged to the country club for decades. I sprinted to the first tee and shook Mr. Snodgrass’s hand. 

“What’s your name, son?

“Hi, Mr. Snodgrass. I’m Lev.”

“Okay, Bev. Nice to meet you. Go on.”

“Great start…” I thought. He couldn’t pronounce my name correctly.

Mr. Snodgrass walked slowly to the first tee to hit his drive. Mrs. Snodgrass followed soon after and we were off! Mrs. Snodgrass’ ball couldn’t have traveled more than 50 yards. I was so nervous on my first loop that I told Mrs. Snodgrass she had 263 yards left to the green, as if she was about to hit a par-5 in two. I think it took her 10 more shots to reach the green. 🤦‍♂️

My job that day was to fore-caddie. Fore-caddying means you’re not carrying a bag, but running along while the golfers are riding in carts. You’re essentially doing the same job you would do for one person while carrying their bag, but for two or four depending on the group size. Fore-caddying was less physically tiring because you don’t have to carry a golf bag, but more mentally tiring because you had to keep track of multiple golf balls, get yardages for every player, and make sure you’re not in anyone’s way. 

Lesson 2: Hard work

Before long, I had several loops under my belt and a few hundred dollars in the little shoebox where I collected my caddie earnings. The money was good for a freshman in high school. You were given cash and didn’t have to worry about grown-up things like paying taxes. I think I finished that summer with 40-45 loops. My parents were proud of me for working the full summer towards my goal. 

I caddied at Rolling Green for five summers. I got familiar with the members and developed a great relationship with many of them. As you move up the hierarchy of the club from a “B”, to an “A”, and finally an “Honor” caddie, you develop a bond with many of the members and they begin to trust you. Initially, all they think you can do well is clean their clubs, but as you gain some experience and show you know what you’re doing members will ask you to read their putts. You develop a knack for knowing their playing tendencies: how far they hit their drives, if they get angry and throw their clubs in frustration, or if they’re cheap tippers. 

I had more than 500 loops over the course of my caddying career. A typical golf course measures around four to five miles if you walk in a straight line… which never happens. Most of those rounds were in the middle of summer when it’s hot and sticky and you constantly have to keep moving so you don’t get hit in the head by a flying white projectile. 

Lesson 3: Interpersonal relationships

You become a friend, a psychiatrist, a comedian to the people you caddy for. You can help your player stay positive or learn how to deliver bad news if they hit a bad shot. You see business deals get made and hear stories about their families, politics, religion. I learned how to have conversations with just about anyone I met and to talk about anything. Listening is an underrated life skill—as a caddie, you practice that all too frequently. 

I did a lot of growing up as a caddie. I saw how even the most wealthy and successful people could be insecure about their wealth when they compare themselves to others. In the end, I understood that grown-ups never actually grew up: they were just a bunch of kids who played outside seeking distraction from their daily lives. I learned how people joke, lie, bully, brag, cheat, and relate to each other.

Caddying helped me achieve my goal of making enough money to buy a set of golf clubs, but it taught me so much more because the lessons I took from those five years early in my life will be with me forever. 

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