Working as a Caddie

Working as a golf caddie taught me to become a close study of emotions and how to tailor conversations with them in mind. In 5 minutes you'd bluntly assess, are they talkative, somber, open to my advice. Everything after that would be a priori, gradually incrementing after they shrugged off or brightened up with a suggestion. It's a pure service job, and I became a sort of chameleon, adapting to hundreds of clients.

In that way, the role taught me to be exceptionally perceptive. It was my job to know and see the things that weren't immediately obvious and be trusted for that insight. In more advanced matches you start to see risk and defend against it towards the middle of a green or short of a hazard. Any advice I gave was never purely based on external conditions but also the emotions of the player beside me.

In the best matches it felt like I was simply verbalizing the next shot. Instructions to draw a 4 iron off the chimney of the white house would be followed by that shot. It was extremely rewarding to have a narrow gap between advice and results. Professionally this is rarely possible and something I deeply miss.

I also noticed that the people I instructed best, and who often performed the best, seemed to share a language with me. We looked at risks and opportunities similarly; my idea of how aggressively they would hit a putt was in line with how aggressively they actually did. Skill was a precursor for this, but the players who were most succesful often seemed to be the most perceptive as well

A seperate, but odd aspect of caddying is that a 14-year-old can naturally advise a CEO. In the best cases that CEO will listen, acknowledging that the 14-year old can functionally know more than him on the grounds of what way the ball will move on the green. In the worst you are a camel, moving bags across a field.

There were some unfortunate sycophantic elements that I was not always enthusiastic about. The role likely crystallized some amount of keep up and shut-up in my personality which I find regrettable. It pushed me toward being overly accepting of blame due to the incentives of my pay. If something went wrong, if not obviously theirs, it was my fault.

I was a caddie for 7 years and worked for around 500 golfers; if anything, I have a large enough sample size to say most people are good.