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Undercover Caddie: Did I make a mistake choosing this line of work?

April 26, 2022
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Illustration by Anuj Shrestha

Icarry for a guy you know, but you haven’t heard his name much the past few years. Still, given what I do for a living, I’m the subject of envy in social settings, and I’d be lying if I said the attention didn’t feel good. Recently, however, I attended my high school reunion, the type of big-anniversary event that motivates you to lose weight to impress your friends, and maybe more importantly your foes. This time I was the one who was envious. I saw how many of my classmates were entrenched in thriving careers with robust families who seemed genuinely happy. On that same trip I ran into an ex-girlfriend, someone who I originally thought was the one, but it didn’t work out because of my transient lifestyle.

It has been four months since that trip, yet I think about it every day and can’t help but wonder, Did I make a colossal mistake becoming a tour caddie?

I love what I do, and I’m glad I chased this dream. I grew up wanting to play, but that didn’t work out, and this was a nice lifeline. I’m sure if I didn’t chase this, I’d be wondering What if? No doubt some of the folks at the reunion looked at me and wished they could switch places with me. However, I’m two decades into working at the tour level, and if you told me where I would be—mostly hovering around the middle—I don’t know if I would do it again. Worse, I’m afraid I’m too far in to get out.

Let’s start with my bank account. It’s OK, but I don’t have to support any-body but myself. I’m still renting a condo because I can’t afford to buy. I can’t tell you the last time I could comfortably go on a vacation, and I always worry that I misread the happy-hour prices at a bar. The past two years I started picking up seasonal work after my player shut his year down early, and that has helped. No offense to anyone who does this full-time, but it’s a blow to my ego to have to grab a holiday UPS route because my main gig isn’t enough. I never thought I’d be rich being a caddie, but I didn’t think it would be this much of a hustle.

I used to embrace the travel, especially when visiting a city or area for the first time. I was up for an adventure every night. But it has become a grind. A human body can take only so many coach seats and couch pull-outs. All the cities begin to look the same. Splitting a house— sometimes even a room—with three other caddies is great in your 20s, but in your 40s, that gets old. I couldn’t ask for better co-workers. Being with the boys is great. All the laughter and good times I’ve had with my fellow caddies more than compensates for the physical toll of looping all these years. But now I’ve reached the point where I’m reliving the same stories with the same people. Sometimes—maybe even most times—I just want to be alone, but on my budget, I can’t afford it.

It’s also hard to date on the road. Whatever momentum you might have is broken by a three to four week stretch when you’re gone. That I’m not swimming in cash isn’t helping my prospects either. Plenty of caddies have families though, so it’s an equation I haven’t solved. If I want a wife, kids and a house, I don’t know if this is the way to get there.

As for my player, we have a good relationship on and away from the course. If I left my bag now, there would be 100 guys happy to grab the strap. We’ve had a rough few seasons, and he hasn’t shown any signs of turning it around. I wonder if the success he had—most of which came before me—is ever coming back. It’s not a dead-end job; I just don’t see much upside.

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Andrew Redington

You’re always one week away from a six-figure paycheck and the security that brings. I had a $30,000 cut from one tournament last year and barely made that much during the next four months. If I’m being honest, part of what keeps me around is the hope that I can, eventually, jump on a new bag. I’m right in that range where I have a lot of experience, but I’m not so old where I’m a dinosaur to players in their 20s. I’m not necessarily talking about hitching onto a rising star; just someone who consistently finishes in the top 75 so that I’m not worrying about where I’m going to work next season.

Another reason I stay is I’m not sure what the alternative would be. I played college golf and my degree is in project management; there’s not a lot of real-world application in what I’ve done to put that degree to use. I’ve thought about trying to find a caddiemaster gig, but those aren’t easy to come by. I could try coaching, but I’d have to start as an assistant, and that’s likely a massive pay cut. When you take a leap of faith in a profession like this, you never really think of how you’re going to leap back.

I know that a mid-career crisis is normal in any profession, so I’m not doing anything drastic yet, but I’m realizing that my career in golf is hurting how I feel about golf. I want to be able to watch the Masters and not be filled with dread that we’re not there. I’d love to be able to go out and play and not be mentally and physically exhausted from working 10 hours on the course. I’d love to be on a hole and feel the wind hitting me and enjoy the view instead of blanking that view out because I’m worried how the wind will affect my paycheck. Forget finding someone to settle down with. I just want to love golf again. —With Joel Beall