Lessons Learned as a Caddie

The summer after fifth grade I started my first job—yes, you read that correct. This wasn’t just some cushy job at the family store or at my father’s company. That summer I began my career as a golf caddie at the local country club. Much to my relief, the club down the street wasn’t Bushwood CC.  In retrospect, the ten summers I spent as a caddie are by far some of my most cherished memories. These ten summers are also the source of some of the most meaningful lessons I’ve learned so far in life. This is especially true for lessons pertaining to what it means to lead, succeed and to put in an honest day’s work.


My time as a caddie was literally filled with countless mistakes. Whether it was misjudging the wind, over-reading a putt, or walking across a golfers line to the cup. I’d be a total liar if I claimed to have caddied a perfect round. At first I managed these numerous mistakes in a very simple, yet unprofessional way – ignorance. I’d continue to walk beside my golfer, avoid all eye contact and pretend like all was fine and dandy. My overall mindset was that if I ignored the issue, then maybe it simply didn’t exist. Naturally, this didn’t go over well with the golfers, nor the other caddies.

In the caddie world, credibility is everything. Someone is literally paying you to tell them what to do and what not to do. That being said, taking ownership for a clear mistake doesn’t go over all too well and feels like a major demerit against your most valuable asset.

However, admitting to a mistake doesn’t always demolish ones credibility – in many ways, it actually increases your overall net worth. After all, how does one go about building trust? One way is to make as many true statements as possible. In many cases, my less than perfect advice led to a poor performance for my golfer. Owning that wasn’t just the right thing to do, but it proved that I stood behind what I believed to be the legitimate truth.


I could honestly retire today if I had a nickel for every time a golfer shrugged off my advice. When this happened, there is truly only one thing to say – hit what you see. These numerous instances definitely did some damage to my ego, but I couldn’t help but admire the golfer for staying true to their convictions.

Caddies have to live in a shot-to-shot world and maintain a sieve of a short-term memory. If your golfer ignores your advice and cranks their approach shot fifty yards over the green, you simply have to shake it off and make sure that they stick their next shot next to the pin.

Regardless of the outcome of the shot, you have to make a call and live with it. There’s no more exposed state than the moment between when your golfer strikes their put and then waiting to see if it breaks 6 inches left to right and falls into the cup as you predicted. The concept of right or wrong cannot be any more clear than it is in the world of caddying. You’re either making the shot, or not making the shot…there’s no in between.

Hard Work Pays Off

A lot of jobs that used to be standard for teens are gone. Nobody delivers morning newspapers on their bicycle, for example. Department stores (remember them?) no longer hire 16-year-old stock clerks. And as any fast food franchisee can tell you, it’s virtually impossible to recruit high school students willing to work hard. Yet caddying demands just that – showing up early in the AM, ready to do physical labor and asking of people a skill like patience because much of the work involves hanging around waiting. All of those are valuable life skills. The sooner they are learned, the better.

Expert Knowledge is Golden

It was very empowering for me to realize that I knew the golf course and knew the yardages. This gave me a great sense of power and accomplishment. It helps being able to share insider information with your player, like how the 150-yard marker right of the 4th fairway is actually 156 (I never told any of the other caddies about this fact). And as I became more attentive to the contours and breaks of the golf course, I felt like I had some valuable knowledge that gave me a competitive advantage. To discover this as a teen was transformative.

Never Back Down

I’ll never forget as a 10-year-old handing my caddie chit to my player for him to check the 18 hole or 9-hole box. Here was the owner of one of the most reputable Cadillac dealerships in the Midwest , unable to figure the form out. At that point I realized that rich people can be stupid just like everyone else and that there’s nothing to fear – or even admire – about them. As golfers they were all equals. As people there was nothing special about them. And from that point on I learned never to be intimidated by powerful people – not politicians, athletes or millionaires. It’s another one of life’s great lessons, and the sooner learned, the better.

Character Trumps All

There’s an old adage about you learning everything you need to know about someone by playing three holes of golf with them. It’s old and an adage because it’s true. That’s especially the case when, as a youngster, you loop for an adult and watch them – how they handle their shots, the rules of golf and their relationship with you. You find out there are all kinds of people and that there’s no necessary relationship between their public persona or profession and how they handle themselves privately.

It’s a lot more complicated than whether they play by the rules of golf or play fast and loose with them. It’s also about how – and whether – they relate to you; how they talk about their spouses and kids; whether they have a sense of humor about themselves or take themselves deadly seriously and blame you (or the golf course) when something goes awry.

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