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Friends, let us pour one out for James William Buffett—Jimmy to his friends and, well, the entire world, the Parrothead progenitor, the biblical Adam of fandom from which all other Parrotheads sprang—who passed away last week at the age of 76.

I was an average fan of Jimmy Buffett’s music—not a Parrothead but a casual enjoyer. There was a stretch of my life when I couldn’t stop listening to it—mostly because the beach is the place where I often feel my happiest, and his music instantly takes me there.

I love the stories of his songs too, though—snippets of relatable human experience that often hit a chord in people: heartbreak (“Come Monday”), enjoying casual dating (“Why Don’t We Get Drunk…”) and feeling overwhelmed by it (“Fins”), the simple joys of a delicious cheeseburger in beautiful surroundings (need I say it?).

Often I listened to his music just because it was a whacking good time—bouncy singalong songs like “Pencil-thin Mustache” or “Livingston Saturday Night.” He was clever with the wordplay, and he made me laugh with his titles and lyrics, like “Last Mango in Paris,” “Jamaica Mistaica.” His music just always makes me feel good.

Since Mr. Buffett (no, I cannot—he is always and only Jimmy) died, for some reason I’ve found myself reading many of his obituaries and other articles about him, and my appreciation has grown deeper. Whether you were a fan of Jimmy Buffett’s music or not, the man has much to teach about both the art and the business of creative careers.

He persisted past failure

Jimmy wasn’t pursuing a music career for even a year before he signed an early recording contract as a country artist. Such heady early success!

His first album was released in 1970, and sold a reported 324 copies. Total.

His next album was shelved (and revived only after he’d had his first hit years later).

By all reports this was a Very Bad Time. There was a bad divorce. Creative disappointment. A lot of margaritas.

But when musical pal Jerry Jeff Walker invited him to come to Florida and check out the scene, Jimmy did (having a creative support system is important, especially to help an artist through the bad times), and that eventually led him to Key West.

And that, friends, was where Jimmy got his groove back.

He took risks and experimented

Key West was a very fine fit for both his personal and professional ethos. Jimmy switched up his jam and started experimenting with other flavors. His music mixed country, calypso, rock, pop, folk, and even reggae to create a sound uniquely his own.

He also started writing more from his own experience and personality, blending storytelling, humor, wordplay, and pathos into his signature style. He started gaining traction with his music and hitting the charts—“Come Monday” made the Billboard Top 40 in 1974.

He changed his genres and he found his voice. Or maybe he found his voice because he took the risk of changing genres.

Oh, and he turned lemons (or limes) into lemonade: those margaritas he drowned his sorrows in after all his setbacks? He blended those into his first major hit from his platinum-selling album Changes in Latitudes, Changes in Attitudes in 1977, making Billboard’s Top 10 in 1979 with “Margaritaville.”

He was smart about the business of his art

When Jimmy learned other people were copyrighting his catchy song titles, he realized the worth of his IP and reclaimed the rights to both “Margaritaville” and “Cheeseburger in Paradise,” and he started to build a brand.

There were T-shirts and footwear. A chain of “Margaritaville”-themed—and branded—restaurants and eventually retirement communities. For a time there was a Cheeseburger in Paradise restaurant chain. He had his business fingers in a lot of pies, actually, with branded hotels, clothing stores, housewares. a “Margaritaville” Sirius radio station, and more.

The biggest hits tapered off by the nineties, and “Margaritaville” was his only song to ever break the Billboard Top 10. Yet Buffett kept pursuing his art, his business, living his damn life on his own terms, Shatnering the shit out of it.

Read more: “Life Lessons from William Shatner”

Think about that—Buffett didn’t create his legacy on a string of enormous popular smashes. He built it on a lifelong body of “midlist” work, a steady output of material.

He worked on Broadway shows, movies, and books (he’s one of only six authors to hit the bestseller lists in both fiction and nonfiction, along with heavyweights like John Steinbeck and fellow Conch Republic denizen Ernest Hemingway), experimenting, growing, exploring his creative expression.

Buffett seemingly knew that no matter how much you love your art and might just want to pursue it (and party, let’s not whitewash Mr. Buffett’s earlier years), forging a sustainable and lucrative career (he was worth roughly $1 billion, according to estimates) often means diversifying, and understanding the business side of the business as much as the creative side.

He lived his life first—and fully

But even with all his financial success, at the core it wasn’t his art that provided his lifestyle, at least not the one that most nourished his soul. It was his lifestyle that provided his art. Buffett wrote about the things he loved—sailing, beach life, hanging out and living large and having fun—and that’s what connected with his fans. Be honest—how many tropical vacations have you taken to the soundtrack of a Buffett album…either literal or virtual?

His music—his art—mattered, but his life mattered more. In a 1989 interview about his move to Key West, Jimmy said, “I found a lifestyle, and I knew that whatever I did would have to work around my lifestyle.”

“I found a lifestyle, and I knew that whatever I did would have to work around my lifestyle.”

Jimmy Buffett

His party years eventually wound down: “I’m not old, but I’m getting older,” he said in that same interview. “That period of my life is over. It was fun — all that hard drinking, hard drugging. No apologies.” But even then he still had a “very happy life.”

And man, why wouldn’t he? He lived it 100 percent. He sailed his own boats, flew his own planes, traveled in the highest of styles. He got mistaken for a drug smuggler (long after he no longer was perhaps guilty at least by association of it) and shot at when flying to Jamaica—with pal Bono on board—and lived to tell the tale in his wry song “Jamaica Mistaica.” He crashed his seaplane off the coast of Nantucket and swam his own self right to shore.

He married, had kids, moved to St. Barts and traveled in the highest of styles. He was authentic to who he was, but he never took himself too seriously. He wasn’t highbrow or pretentious. He was Jimmy, the guy you like to wear leis and drink and dance and sing along to. He knew who he was, and he knew who his fans were, and he connected on that level with his Parrotheads.

He endured

Right up until his death, from a rare form of skin cancer, Buffett was still playing his music, still connecting with fans. His last show was in July of this year, a surprise appearance in Rhode Island. His art was a part of who he was and he kept at it till the end, when he passed away surrounded by family and friends.

I don’t know, folks. If I die with a belly full of life experiences under my belt, having lived life on my own terms (or as much as is possible in the world), with loved ones at my side and my art having connected with at least a handful of people, I think I’ll call that a pretty good life.

So let us lift a glass (of your choice, but a margarita would be poetic) to Jimmy, a man who filled people’s lives with music, joy, and vacation vibes—and maybe still has a little bit to teach us about how to live them.

Bring it, friends—I want to hear your Buffett experiences: what he or his music meant to you, your stories, your thoughts. The man deserves a moment to be remembered.

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