10 Key Takeaways from the First 10 Caddyshack to Corner Office Interviews
In our first four months, Caddyshack to Corner Office has been fortunate to conduct 10 interviews with uniquely successful people. Each of them has described how caddying was a transformative experience, with many saying it's the best job that a young person can have. Because caddies are able to work for and truly provide value to highly accomplished people, the profession offers benefits that most other jobs simply can’t, like developing a network of adults away from your parents and gaining financial independence as a teenager. For your convenience, here are the 10 most consistent themes distilled from our first 10 interviews.
Caddying provides or instills...
1. Unparalleled mentorship and guidance
John Ashworth: This is how cool Payne Stewart was! I’m not even caddying but get to stay the whole week. The entire time, he’s picking up all the dinners, and we went to a couple movies. He was such a good dude, so strong mentally. It was really great to be around that. It was great to be around someone so successful and see how he treated the process.
Neil Jacobson: I loved being around the type of people that I caddied for. They were so successful, classy, and elegant. They constantly pushed themselves: how they dressed and how they spoke, even when arguing with each other. I was highly impressionable at that stage in life, so these people were very inspiring to me.
Mary Petrovich: There was one member with whom I shared a particularly close relationship. Her name was Suzy. She was stunning, kind of like Goldie Hawn with a great smile. She was petite, always upbeat, and loved golf. All of the boys wanted to caddie for her and became jealous when we developed a very intense personal relationship. She became my mentor. There’s actually a book written about her called, If You Knew Suzy. One of her daughters, Katie Rosman, a writer for the Wall Street Journal and New York Times, wrote it after Suzy passed away far too young, and I'm actually a chapter in the book because we were so close. It has kind of come full circle. I won the club championship at Franklin Hills in my first year (as a member), something Suzy had long tried to do, so I then dedicated that special win to her.
2. The value of partnership and service
Mike Keiser: Being a caddie is about being a good partner. I’ve luckily had good partners, like my friend Phil Friedman. Another great partner was Howard McKee who led the charge at Bandon, as are the incredibly talented course designers David McLay Kidd, Tom Doak, Jim Urbina, Bill Coore, and Ben Crenshaw.
Jeff King: It’s the funnest thing in the world since you’re going to have more bad days than good. But I love that every day is a new challenge. You get to prove that you’ve gotten better. And when everything clicks, it’s the best feeling in the world. You’re helping them hold the trophy and taking down that flag on the 18th green!
Neil Jacobson: Whether you’re a caddy, a carpet salesman, an assistant, or a record executive, you’re going to have to take a lot shit and repeatedly get the short end of the stick. But instead of being a cynical idiot focused on the downside in those situations, I believe that the real winners in life are able to continually provide exceptional service.
3. Confidence
Matt Desch: I think that it was the first activity that I had where I could develop a level of expertise that was appreciated and rewarded. Over a few years, I became extremely good at caddying to the point that the head pro and others would ask for me to be their caddie, as they knew it would help their game. I developed “status” with the other caddies, and the pride that developed from doing a great job and getting a big tip was very satisfying and fulfilling. Plus, I’m sure girls loved my “caddie tan.”
4. Responsibility and performing under pressure
Mary Petrovich: My father died suddenly, widowing my mother at age 30 with eight kids. I was the second oldest and the eldest female. I was seven years old at the time, and my older brother was eight. Several of my siblings were still in diapers, and we had no house or insurance. The good thing is that you don’t realize how poor you are at that age; you just do what you’ve got to do in order to live. I started caddying at Franklin Hills Country Club when I was 12 years old. It became my full-time job for nearly eight years. I’d caddie from March to November, starting at dawn and working until dusk, sometimes completing three loops in a day.
Stephen Malbon: More than anything, it was how to handle yourself in high profile situations. You’ve got two millionaires almost fist fighting on a hole, trying to decide if the one guy made a 7 or a 6 because there are thousands of dollars at stake. I learned about staying calm in high pressure situations. Reading the putt in big moments and telling your guy to split the lip, don’t play it outside the hole. Maybe he hits a perfect putt but it lips out. Whether he makes it or misses it, being in it, I loved all of that.
5. Healthy competition with peers
Neil Jacobson: Well, first you have to start at the caddy yard. Those guys were tough. It was like a pit, brimming with what would probably be described today as toxic masculinity. The other caddies are not there to help you. They test you, play pranks on you. There’s a hierarchy and a sort of pack mentality. You have to pay your dues. It was really great for me, really toughened my skin.
Mary Petrovich: My goal was to become the best caddie there. I was fortunately born with some God-given athleticism and was accustomed to not only competing with but beating boys in school relays and recess basketball games. In my first season, I completed over 200 loops and was named “rookie caddie of the year.”
6. Teamwork
Fritz Corrigan: It was at Interlachen that I really found my stride as a caddie. I’d work during the day and then go to hockey camp at night. Hockey was and still is another great passion, and I learned a lot about teamwork on those long days. Caddying you’re not only working with your player but also with the other caddies. You knew who was good and who wasn’t, who would catch a pin for you while you’re raking a bunker. Stuff like that. You learned the importance of teamwork and being a good teammate, which obviously translates to the ice as well.
7. Leadership
Matt Desch: So many lessons come from caddying but one of the most important is listening and observing. Being a leader requires vision, the ability to communicate and inspire, but if you aren’t perceptive to the environment around you, you’ll miss critical information needed for success. Sometimes the most important thing is to watch and listen, and only speak when the time is right and you have something to say. That’s what a good caddie does; he or she watches and observes carefully before starting to provide advice. Getting along with 60 other kids all summer in close proximity between jobs was also an invaluable experience. It toughened me up and helped me relate to anyone at any level around the world.
Fritz Corrigan: Our leadership team settled on three things: integrity, courage, and commitment. Since Cargill operates many businesses around the world, leaders had to have the integrity to turn down a bribe or say no when one is asked of them. They had to have the courage in the grey areas, like recognizing when someone on the team isn’t cutting it, and a change needs to be made. And they had to have the commitment to never quit and see things through. We found that when you exemplified those traits, people were going to follow you. And looking back for me, all of those values began to form when I was caddying, like with the story about my dad’s tee shot and many others.
8. Friendship
Jim Nugent: I most enjoyed the camaraderie. Caddying was fun. You were outside, and the money was good. You were also learning proper and improper ways to conduct yourself. But ultimately, it was about hanging out with my friends, the other caddies. We had the same work schedules, so we spent a lot of time together. Whether it was playing cards or horsing around during down time in the caddy yard, going to bars at night, playing golf on Mondays, or attending a ball game together, it was a way of life for us.
John O’Donnell: The caddie yard was also a good scene, a whole bunch of guys packed in there playing cards. You wanted to get out as soon as possible, but you also wanted to get the best loop that you could. So it was a dance. You didn’t want to get stuck with some jerk. To top it off, this was the golden era of tennis. Borg, McEnroe, Connors, Lendl and we’d all watch Wimbledon and the US Open down there. Everyone was into tennis. So sometimes you’d have Borg playing McEnroe into the 4th or 5th set, and it’s triple break point. All of the sudden, the caddie master calls your name for a loop, and you’re like, “I can’t leave!”
9. Tough but fun work
John O’Donnell: I swear I was probably carrying 80% to 90% of my body weight each loop. It was so bad that members would ask, “Can we help you?” I’d say, “Nope.” But when we’d get off of the 17th green and I’d give them the driver for the 18th’s tee shot, I’d go lean up against a tree in the rough, forecaddying. I remember thinking, “I’m just so glad this is over.” Those were some hot days in Chicago.
John Ashworth: I just remember how grueling the work could be on those hot summer days. Shit man, La Costa is a long course. When you were coming down the stretch at 15, 16, and 17 right into the wind, those old leather bags were tearing into your shoulder. It was so uncomfortable, and you’re just hoping that you won’t get stiffed!
Stephen Malbon: Caddying for people playing for a lot of money is the most fun job I ever had!
10. Constant learning...
a. About golf
Fritz Corrigan: I really enjoyed learning the game. You came to appreciate good shots and good golfers. I also gained tremendous satisfaction from doing a fine job as a caddie and earning a nice tip. There was a sense of accomplishment.
b. About people
Jim Nugent: Working as a caddy, I became determined not to be a jerk. You saw everything on the job, and many people were absolute jerks to the caddies or to the staff. I decided that life is too short to treat people poorly. So for me, it wasn’t as much learning what I wanted to be but rather what I didn’t want to become. That was the biggest lesson, and it has served me well.
c. About life
Mike Keiser: You learned about golf, but you also learned a lot about life, what it meant to work hard, and what it took to be successful.
