9 Reasons caddying at a country club is a great summer gig

By Nick O'Brien · April 30, 2021

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Caddying at a country club is an awesome gig for so many reasons. I’ve been a caddie for four years now at Siwanoy Country Club in Bronxville, New York. I’m a junior at Southern Methodist University and while all my buddies have been stressed about internships since graduating high school, I’ve been working the best summer gig out there.

Today more than ever, there is an emphasis on internships and getting a jump start on your career as a college or high school student. Obviously, taking care of your career and pursuing elite jobs is great, but being a caddie opens doors into a post-academic career as well. Oh, and you’ll have way more fun than any of your buddies stuck at a cubicle.

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Here are my nine reasons you can’t find a better gig this summer:

1. It is GREAT money

Obviously, the most important question about any job is going to be the pay. Well — if done right — caddying can be one of the best paying summer gigs out there. Forget your friends and their internships stuck in a cubicle all day (I’ll revisit that later). You can probably make more than them and have a way better time doing it.

2. You learn a ton about the game

Whether you have golf experience or not, caddying can teach you a ton about the game. Your entire job is based around having your golfer succeed in his or her round and, in that, you spend most of your time out there thinking about what the right shot is, or what a certain putt is doing. Point is, you are going to become a much smarter golfer after spending some time as a caddie.

3. You learn about a lot of other things

Spending four hours side-by-side with someone is bound to lead to some conversation and at a country club you are typically carrying for some pretty smart, successful people. You learn about what type of work they do, where they went to college and ultimately, you can end up having some pretty interesting conversations. Through my years of experience, as a college age kid, the people you caddie for are almost always fascinated to hear about your life and what you’re interested in. Mentioning you are a student to your golfer almost always sparks a nostalgic smile and you end up exchanging stories and information about your college experiences. I’m not kidding. This happens almost every time I caddie for a golfer for the first time.

4. You are outside

This one may seem obvious, but really — you are outside in the summer all day long and you are not sitting in an office or a restaurant or behind a cash register. You are walking with two golf bags on your back once or twice (if you’re lucky) a day while your buddies are miserable staring at a screen all day.

5. You learn how to talk to people

This one reason might be the only reason needed to convince kids to caddie. Like I said, caddying at a country club pretty much means the people you are caddying for are successful in some regard. Learning how to impress, laugh and entertain a “customer” is a life skill and these are all things caddies can do on the golf course with their golfer. It is so common to hear people talk about how the “little things” often separate people and by caddying you learn a lot of the little things when it comes to manners, eye contact, communication, etc.

6. You might caddie for your future boss

Again, a country club can be filled with successful businessmen and women and through weeks or years of caddying for them and impressing them, you can network these individuals to further your career. I imagine most people would be surprised at how many people I know that found a career through caddying, but the honest truth is the people you have caddied for multiple times probably enjoy your company — otherwise you would not have continued to be their caddie. One of the biggest reasons this summer job is awesome is that it is such a unique and effective way to network.

7. Your work ethic develops and strengthens

Caddying in the summer is such a fun and unique summer job, but it requires a certain level of commitment. I used to be in the caddie yard by 6 a.m. most summer days and somedays were very slow and I wouldn’t get work. This time pays off though, and your caddie master will notice the hours you put in and want to reward you. This aspect off caddying has prepared me so well for school and working a job in college because I learned very early how to wake up and start my day when most other people were not.

8. It is an exciting job

One of my favorite times to caddie is when I have a foursome that is looking to gamble and possibly have a couple drinks. There is nothing more rewarding than a fun group of four golfers playing for some money. As a caddie, you feel some responsibility in helping your golfers win their money and giving a good read when there is some cash on the line is an all-time feeling. Don’t get me wrong, the flip side of that situation is always a tough feeling and I have had my share of those but nonetheless, it is a really exciting job.

9. It is FUN

Obviously, the other reasons on this list probably lead you to believe it is a fun job. But seriously, it does not feel like work sometimes. You get paid pretty handsomely, in cash, to have a good time on the golf course with some people that you respect and some people that you could impress enough to one day work for. Even without networking, caddying for a group of golfers that just want to enjoy a summer afternoon and have fun is a pretty good way to earn your money. Ultimately, caddying is the greatest summer gig out there, almost to the point where if you do not caddie in your summers, you’re doing something wrong.