A Pirate Looks at 76

Warren Ward |

The music world lost one of its most successful citizens a couple of weeks ago. Many of us were touched in one way or another by Jimmy Buffett’s music over the years but, in thinking about his life, I wonder how much of what we saw was actually a character he created. While he loved to describe himself as a pirate, Jimmy didn’t steal other people’s money. He worked hard in the early days, invested wisely, and made his own money work for him - something fairly rare in his business and not nearly as much fun to write songs about.

Switching from the trombone he played in high school to the guitar so he’d be more popular, he found a way to portray a laidback beachcomber while writing and performing hundreds of songs, releasing fifty-eight albums and making uncounted tour stops. That sort of productivity doesn’t seem to correlate with the slacker lifestyle he projected. So, what was really going on?

Early in his career, Jimmy opened for acts such as the Eagles and Fleetwood Mac, touring as hard as they did. Once he became an established star, he famously performed only three days per week, Tuesdays, Thursdays and Saturdays. Similarly, we suggest that our clients work hard enough to amass a sufficient nest egg to see them through retirement, but we also encourage a sensible work/life balance. One of our everyday comments is: at the end of their lives, very few people express a desire to have worked more. I doubt if many of us will be able to manage that as well as Jimmy did.

Jimmy wrote about what he loved: boating, fishing, surfboarding and flying. Well, those plus drinking, although according to various reports, he gave up both drugs and alcohol in his mid-thirties. In addition to his laid-back lyrics, he was also known for his devoted fans, called Parrotheads, who often followed him around the country. According to the AP, in 2012 Buffett described them as "the social network before there was a social network" because they "had something in common; they shared things." In the spirit of sharing, he contributed to the music of others, co-writing with ex-Beach Boy Brian Wilson (South American) and country artist Alan Jackson (It’s Five O’clock Somewhere). He also put on performances for causes, playing at military bases and to raise money for Manatees, hurricane relief and once in Hong Kong for needy children.

His music often touched on the passage of time. His song A Pirate Looks at Forty reflects on aging and unfulfilled plans. He wrote it about a friend who was taking stock of his life, having reached that age. A couple of the lines are: Yes, I am a pirate, two hundred years too late . . . I'm an over-forty victim of fate. The theme was so resonant for Jimmy that he titled his autobiography A Pirate Looks at 50 – this time talking about himself. His book is part life story and part travelogue. It is filled with his love of being near the ocean, spending time fishing and boating. One theme that runs through the book is that he and his wife, while long married, maintained separate interests as well. On one trip, he describes hanging out with his guy friends, while his wife brought her own friends along for the trip. We’re planners, not therapists, but we do encourage couples to maintain and/or develop individual pursuits, especially as they plan for retirement.

Somewhere in middle age, Jimmy connected with another reasonably successful Buffett, namely Warren. Although not related, they called each other ‘Cousin Jimmy’ and ‘Uncle Warren’ and it seems that Jimmy learned a lot about investing, maybe even life, from that ‘uncle’. Perhaps with Warren’s advice, or perhaps through learning from earlier mistakes, he became an astute businessperson, selling Margaritaville-branded merchandise including liquor, flip-flops, and retirement communities. Earlier this year, Forbes magazine included him in the annual listing of billionaires (yes, with a b).  

According to his social media accounts, “Jimmy passed away peacefully ... surrounded by his family, friends, music, and dogs. He lived his life like his songs till the very last breath and will be missed beyond measure by so many." Jimmy died at 76 due to a very rare and very aggressive form of skin cancer. It’s possible that his near-constant time outside in the sun may have shortened his life. We’ll never know if Jimmy would have traded a life spent indoors for a few additional years on earth. I think we can guess what the pirate’s answer might be . . .