While as I commented, Jimmy Buffett isn't very consistent, but I did enjoy the book. It is great that a guy that writes and sings songs, performs, and writes books can create a life as cool as his. Is he really happy? Well it sounds like after a lot of drugs and analysis, and finding a way to finally get along with his second wife, he just may be, at least at a superficial level.
He certainly comes in pretty well on the "he who dies with the most toys wins" scale. Having both a Cessna Citation and a Grumman Albatross is pretty big in the toy department, but it sounds like there are other planes in his private airforce as well. On top of that, houses in Key West, Long Island, Aspen, and it sounds like a Caribbean Island for two. Lack of money and things are not on his list of problems.
It seems that he has discovered a couple of hobbies that he cares about deeply: flying and fishing. He has the resources to be able to pursue those way farther than most people, but he is interested in personally doing well at both of them, and uses the money to help that with guides, co-pilots, training, equipment, etc, but he does get fulfillment out of the accomplishments. He enjoys music, performing, and in many cases the interactions with his fans.
Sort of like the song "Wasting Away in Margaritaville", he pretty much sells escape. The whole Caribbean, Gone Fishing, gone flying, on vacation mentality. He must be a good deal more of a businessman than he lets on, but that is probably part of the deal. To some degree, he IS the product. He is the poster child for the "Jimmy Buffett lifestyle".
The book is well written and fun. While it seems unlikely that the planet could support very many folks living his lifestyle, it is pretty amazing that there is one ... and he doesn't even feel rich!
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