Jimmy Buffett (AP Photo)

After many years, I finally got an opportunity to see Baby Boomer icon and “Cheeseburger in Paradise” singer Jimmy Buffett in concert here at Denver’s Pepsi Center.

And in addition to confirming all of my not-so-incorrect notions about the Parrothead Nation, partying it up in the parking lot and doing the fin dance in the stands, I also got a bit of insight into how Buffett and his generation will be easing into retirement. Maybe “easing” is the wrong word. Perhaps not even retiring at all.

Buffett, perhaps unbelievably, turns 65 on Christmas Day. And as the seemingly unstoppable purveyor of beach- and booze-themed good-time music, the venerable performer (who aptly described himself as “just a goofy guy from Alabama”) has turned his post-teen summer job as a musician into one of the music industry’s biggest money making machines. For more than four decades.

Not that Buffett (who, yes, really is a distant cousin of that more financially famous namesake, Warren), hasn’t had his share of missteps along the way, ranging from the occasional floatplane crash to his more recent and well-publicized face plant into the audience at a show in Sydney, Australia.

Barefoot and as energetic as ever, Buffett told the audience he now remains a little more careful during his on-stage gallivanting, though he shows few signs of his impending status as a potential Social Security recipient.

Part of the performer’s charm—and his sheer ubiquity—is his perhaps not accidental decision to diversify his operations, especially as the recording industry began to tank in the early 00s. His Margaritaville cafes launched in Key West, Fla. and now include restaurants and hotels across the world, including a recently opened casino in Las Vegas. And his branded tequila, beer, frozen food and merchandise empire continues to grow; there’s also footwear, a satellite radio channel and, of course, those 26 studio albums and 11 live albums.

He’s also become a best-selling author. But his most important commodity is his relentless touring schedule, an enterprise that grossed more than $215 million between 2000 and 2010. Fans count the number of times they’ve seen he and his Coral Reefer band as a point of pride, and the shows never seem to end.

Sounds like your typical on-the-cusp-of-65-year-old, right? Maybe his financially bulletproof cousin offered him some advice over the years. Whatever the case, the sheer scope of his parrots and palm trees escapist lifestyle has certainly guaranteed him a successful and comfortable life as a (gasp) senior citizen. Can you say the same for your Boomer clients?