Lessons I Learned from Caddying

I looped from the age of 13 until I was 21.

Many of my fondest memories of that time involve wearing a caddie bib. Caddying is a great gig. You learn how to talk to adults, glean insight into people’s true character, and come to understand why people love to spend their day on a golf course. It was a formative experience for me, not to mention a solid way to earn cash (all of which I definitely reported to the IRS).

I learned many lessons during my decade caddying, many of which I still leverage daily.

Lesson 1: showing up

As the cliché goes, a good caddie should “show up, keep up, and shut up.”

Keeping up and shutting up can be important, but even more critical is showing up. Rolling into the caddie shack at 6 a.m. doesn’t always sound appealing, but it’s a tremendous way to develop discipline.

At the golf course where I worked, every caddie who showed up by a specified time received an entry into a lottery. The number you drew determined the order in which you’d be assigned a bag. Sometimes your ball got drawn first; sometimes you were 24th. Unmotivated caddies stopped showing up after drawing the 24 ball a few times. The hard workers kept showing up. That’s not a phenomenon unique to the caddie room.

Driving home with a few hundred dollars in your pocket doesn’t feel as sweet if you don’t know the feeling of driving home penniless after waiting around for a few hours without getting a bag. Hoisting trophies doesn’t feel as sweet without knowing the taste of a missed cut. Receiving a promotion at work is more gratifying after you’ve doubted your ability to succeed.

Life is uncertain and casts doubt on whether or not things will ever go your way. People with determination keep showing up anyway.

Lesson 2: owning mistakes

I’ve experienced some low points, but I might prefer personal struggles to the feeling of watching a putt break in the opposite direction of what I told my player. Everyone saw what just happened. There’s no hiding from it.

Fortunately, every human being gets things wrong every day. The best poker players in the world make massive blunders. Brilliant entrepreneurs make awful predictions about the future. You can tell quite a bit about someone’s character from the way they handle their mistakes. Deleting a tweet that ages poorly reveals something about the tweeter!

Caddying puts you in a position where you must be responsible for your mistakes. Wriggling your way out of admitting to fault is a terrible but tempting route. It’s an awful habit to pick up, and a hard one to break.

Sometimes you give a bad yardage. Sometimes you drop a head cover. Sometimes you bet with other caddies on which hack in the group will take the biggest divot of the day and your player catches you showing his 22-inch divot to the other caddies in your group like it’s a trophy fish.

Mistakes happen. Own them.

Lesson 3: generosity

I caddied for a lot of bad golfers during my caddying career. I caddied for people who threw clubs. I caddied for people who berated me. But by far my least favorite player to carry for was the person who talked nicely all day and smiled superficially while handing over an atrocious tip. Treating a caddie with respect is not a substitute for compensating them. If you can afford a $16 cocktail at the turn, you can afford to take care of your caddie or another caddie in your group.

A good tip versus a bad tip often made or broke my day. Caddies are in a vulnerable position. Having been in that position has helped me understand the importance of compensating others in the service industry. The gesture is worth far more than the dollar amount.

Sure, a smile can make someone’s day. But you’re not buying yourself lunch and a Gatorade with a smile.

Lesson 4: companionship

A walk with a caddie is a much better experience than a ride in a cart.

Your cart can’t read putts or run up ahead to spot your drive. More importantly, your cart doesn’t walk alongside you and share the experience of your round. There’s something inherently special about the relationship between player and caddie, practitioner and assistant.

As attentive as your golfing friends may be, nobody is paying attention to your lies like your caddie is. Nobody else appreciates the difficulty of the flop shot you just pulled off or laughs with you after you skull a straight-forward chip over the back of the green and into the trees. Your caddie is with you every step of the journey.

Caddying taught me that no matter the journey, it’s more fun with others by your side.

Lesson 5: keeping at it

For caddies, the worst stretch is holes 8 through 11, especially if you’re double bagging and on your second round of the day. You’re fatigued, you’ve seen a lot of bad golf shots on the day, and there’s a lot of golf left.

Like other trying moments in life, most of which are more serious than the challenge of carrying someone’s golf bag, the key is to keep going. Caddying prepared me for times when I have gotten close to giving up.

Even when a difficulty seems like it’s going to last forever, the 18th hole is always right around the corner. Eventually your head will hit the pillow, and tomorrow the sun will come up. You might even be in the caddie room to watch it rise.

Any ex-caddies (or current caddies) out there? Which lessons did I miss?