The Portland 54: Embrace uncertainty

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On Friday I had the honor of playing in The Portland 54, an annual golf tournament that has been played for the last 17 years. It was started by a group of guys at ESPN who wondered if it was possible to play all three 18 hole golf courses in Portland, CT in a single day. 

Turns out it is. All three courses are less than three minutes apart.

Play the first 18 holes at Portland West at 5:00 AM.

Play the next 18 at Portland Golf at 9:30.

Play the final 18 at Quarry Ridge at 3:30. 

The scores from the first two rounds of golf determine the teams for the final 18 holes, which are played as a scramble. The winning team in the scramble is declared champion and takes possession of the trophy for a year. The trophy was purchased from eBay and dates back to the early 1900's. It was originally a trophy for a women's contest of some kind. It is old and a little ugly and glorious.

Winners traditionally drink Rolling Rock from the cup at the end of the tournament. 

I was able to play because every year, one rookie is added to the roster of 16, and this year I was the lucky one chosen. I didn't know anyone in the tournament, but the commissioner is a Speak Up fan and regularly attends our shows. He found out - maybe through this blog - that I was a golfer.

When I received the invitation, some of my friends advised against playing in the tournament, for several reasons.

  • 54 holes of golf in a single day is insane.
  • I didn't know a single person playing, which meant I'd be spending at least 15 hours in the company of strangers. 
  • This could be a scam. I might end up dead.

In the end, I took the advice of a friend who said that I had to play, for several reasons:

  1. It's golf. As bad as it can get, it's still better than most things.
  2. It's an opportunity to meet new people and make new friends. 
  3. Guys who are able to get together like this for almost two decades can't be that bad.

All of this turned out to be true.

The golf was great. I started to lose my mind (and my swing) during holes 13-16 of the second round of 18, but I powered through and finished strong.  

I met some fantastic people. The commissioner of the league might be the best golfer I've ever played with. I also played with his son, his son-in-law, and a cast of other characters.

I met a guy who is a ball hawk, diving into the woods whenever possible to find lost balls. He probably found three or four dozen balls over the course of the day.  

I met a guy who holds his club with a reverse grip, which looks incredibly painful but is surprisingly effective. 

I watched two guys putt by looking at the hole instead of the ball.

I played with funny guys, serious golfers, quiet guys, and everything in between. 

My day was not without incident. Over the course of the three rounds, I managed to bounce my ball off a rock outcropping and land it on the green for a birdie. I hit two rakes - both which sent my ball back into the trap. I hit several cart paths. Many trees. One golf cart. I ate a bug and had a bug land directly in my eye. I lost a ball on a fairway.    

Of the 16 players, my score ranked 13th. I shot an 87 on a par 60 and a 109 on a par 72.  

Not good scores, but this is the summer that I change my swing. I am hitting the ball better but also decidedly less consistent. 

Sadly, lightning interrupted our final round, so The Portland 54 ended up as The Portland 47 for me. Happily, we will be returning to the course later this summer to complete the final 18, so I'll have a chance to see the guys again and play some more golf.

I know people who would have passed on an opportunity like this.

  • 54 holes of golf might have seemed like too much.
  • Surrendering an entire day to a golf tournament might have been hard.
  • Playing with 15 strangers might have been unnerving for some, especially if they play like me.

Mostly, it's uncertainty that prevents us from trying new things. The unknown is scary. Taking risks is frightening. Daring to do what seems a little crazy is something people tend to avoid. The inability to perceive the future and accept the consequences of uncertainty traps so many of us in the present. We fail to move forward. Our lives remain static. 

I have learned to embrace uncertainly. Accept possible failure. Say yes when opportunities arise. I'm not entirely sure why, but I suspect that two near-death experiences, a violent armed robbery, and near imprisonment have taught me to do everything I can while I still have breath. 

As a result, I end up standing on stages around the world. Launching seemingly nonsensical businesses with my friends. Meeting new, remarkable people. Trying new things.

Playing 47 holes of golf with 15 great guys. 

I am a happier person for it.