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Eric Douglas: Looking at 50


By Eric Douglas

I turned 31 the year that Jimmy Buffett’s book “A Pirate Looks at Fifty” came out. I read it with enthusiasm hoping to learn about a life well-lived and make a plan for my next 20 years. That was 1998.

If you don’t recall, Buffett is the singer/songwriter/author most famous for the song “Margaritaville” that has turned into an entire industry of its own. Buffet was by no means a one-hit-wonder, though. He has dozens of albums and a summer concert tour that is still going strong, making him one of the top grossing artists of all time -- with only two “hits” to his name. Another of his songs that any Buffett fan will recognize is “A Pirate Looks at 40,” a story about a character out of time and growing older.

Buffett’s personal life reflects the song “Margaritaville” with a lot of time sailing and flying around the Caribbean full of adventure, music and rum. That was the dream for all of us who read the book at the time. We hoped to be able to live that life by the time our own 50th birthday rolled around. Back then, it seemed like a long way off.

Flash forward 19 years and my 50th birthday is tomorrow. I am rereading the book for some perspective.

I will freely admit that I’ve done some cool things and had some amazing experiences along the way. I’ve also made some mistakes and accumulated some regrets. I think that’s the nature of life. There is no way to fly high without stumbling from time to time. Things didn’t go perfectly for Jimmy Buffett. Among other things, he did actually break the same leg three times in one year.

That’s probably the greatest lesson I’ve learned in the first half of my life. (Yes, I expect to live to be 100.) There are ups and downs, hills and valleys. The downs are as much as part of life and how we handle them probably says more about us than the ups. Considering everything I’ve been through in the last year and a half, it’s time to climb back up that mountain.

It’s funny, though. I don’t feel old, like I thought 50 would be when I was 30, either.

Yes, I am a pirate, two hundred years too late

The cannons don’t thunder, there’s nothing to plunder

I’m an over-forty victim of fate

Arriving too late, arriving too late

-- Jimmy Buffett

Eric Douglas, of Pinch, is the author of “Return to Cayman,” “Heart of the Maya,” “Cayman Cowboys,” “River Town” and other novels. He is also a columnist for Scuba Diving Magazine and a former Charleston Newspapers Metro staff writer. For more information, visit or contact him at


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