No Pain in the Ask
This is how I became a caddy:
“There’s someone down at the range you should meet,” said Keith. He was the head golf professional where I worked as the club’s “starter.”
He told me that warming up was the caddy master at a cloistered old club here in New Jersey. So I made my way to the range.
“How do I play Somerset Hills?” was the first thing out of my mouth. Now I’ve never fancied myself as an assertive type, but the words sort of just spilled out.
He asked me what I was doing tomorrow. “Playing golf at Somerset Hills?” was my response in the form of a question.
I was correct.
And so I did.
Not knowing the protocol, I asked around.
“How much should I bring for a caddy? What should I wear?”
When tomorrow came around, the nerves set in.
I had learned the game as a kid in Florida. Sneaking on the public course near our house, I was forever dodging the rangers in an attempt to hide my modest beginnings. Tomorrow would be an introduction to another world.
Arriving at Somerset, I was greeted, not by playing members, but by caddies. I learned that, on Mondays, the course was closed for regular play. Mondays were “Caddy Days,” i.e., days reserved for caddys. To play the course.
I got paired up with two caddies. Tommy and Chris. Tommy was the reigning veteran caddy. He was in his sixties, having caddied there since he was 14. Chris was a soon-to-be club pro.
They were gracious hosts, showing me around the course, treating me as an equal. All the while encouraging me to join their ranks as a looper.
Standing on the second tee at Somerset, confronting the par 3 “Redan” hole, I was mesmerized by what I saw. I had never encountered a hole like “Redan.” 
From that moment, I was better for the asking.