5. Figuring out how to beat the course AND the other players

But reaching that top tier is no easy feat in a crowd of talented loopers.

“You’re on the road in the car usually quite a bit; you only fly when you have to. It’s a grind, it gets expensive,” Wynn says. “The only guys making a good penny are the ones winning a lot.” 

And while talent certainly plays a part in who rises to the cream of the crop, luck is an indisputable factor in who takes home that bigger paycheck. 

“For every one caddie you see on tour and you know about, there are 20 or 30 other guys who are their equal as far as type of job they do and what they offer,” Wynn says.

It’s that element of luck that makes the job frustrating at times. Wynn says the most difficult aspect of his unusual occupation is figuring out how to beat the course — and then the other players. A golfer might be on pace for a 66 or 67, but just a few tiny errors can knock that back to a 71 or 72. And in professional golf, minuscule differences in play can add up to big differences in the score. 

“It’s unpredictable; you don’t have a clue on any given day what will happen until you get in the flow of a round,” Wynn says. “Some days it just goes perfect — but not very many.” 

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