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  Three things my friend Jimmy Buffett taught me about life and business Buffett was as talented an entrepreneur as he was a musician, author, sailor, and aviator. He never forgot about keeping successes and failures in perspective. 6-Sep-23 – Everyone who ever worked with Jimmy Buffett, and I did, will tell you the same thing about him. Which is that they took far more away from the experience – however fleeting it may have been – than simply a love for the guy and his music. He was every bit as successful an entrepreneur as he was an entertainer, and he brought the same focus, passion, and enthusiasm to whatever he did. The insiders’ joke was that he was about the least “laid-back” guy you were ever gonna meet. Whether it was music, his Margaritaville-themed businesses, charity, or politics, it was the same story – if he was in, he was in 110 percent, and he did everything with a vengeance. Jimmy was direct, down-to-earth, and deliberate in his dealings with you whether you were a peasant or a prince, although he never paid attention to those kinds of distinctions. And that openness, attitude, and approach never changed over the more than 30 years that I knew him. So, it’s a little surprising to hear from so many people that they had no real idea that he was such a substantial businessman in addition to being a great writer and musician. I’m reluctant to add “philosopher” to the encomium because he always hated it when anyone used such highfalutin terms to describe him. He was thoughtful and certainly took a great deal of pride in his craft and worked his butt off to make that happen. But he was also amazingly modest and always said that he was just one of the guys who got far luckier than he ever expected or deserved. And, he’d usually add that the luckiest thing in his life was his family. I know he usually meant his immediate family, but there were plenty of others in his various circles who felt that familial bond as well and knew that – if the need ever arose – he’d be there for you.
1 Your work is what you do, not who you are. It’s difficult for any new business builder to separate himself from the business – the best entrepreneurs never leave much of anything at the office at day’s end – and taking things personally and to heart is critical to their eventual success. The ones who care the most win. But maintaining a healthy distance between what you do and your own identity and self-worth is crucial to your mental health. And when you’re a celebrity – and a walking lifestyle like Jimmy was – it’s even harder sometimes to remember to separate your public “persona” from the work and the audience’s response. No one’s happy-go-lucky all the time – it’s not part of the human condition. Performers face a far more immediate and regular test of their efforts every time they cut a record, perform, write something, or offer new material to the world because the world – especially these days – is a picky and nasty place. When he faced criticism, complaints, and even outright rejection or disappointment, Jimmy always took a step back and said that he could only do his best and that, as long as he did that, he could live with whatever came after. Success is fleeting, but excellence is forever. His work was a wonderful part of his life, but making a living was only a part of making a life worth living. 2 Take your work seriously, but not yourself. It’s easy as an entrepreneur to convince yourself that the weight of the world is on your shoulders, that everyone inside and outside of the company depends on you, and that the work you’re doing is the most pressing and important work around. And it’s sadly too short a step for too many people to translate that actual and awesome responsibility into the belief that your shit doesn’t stink. An entrepreneur needs plenty of self-confidence, but that power and passion need to be tempered from time to time with some self-awareness as well. Jimmy could always laugh at himself. He’d sometimes catch himself pressing a little too hard, lecturing out loud, or even pontificating, and – full stop – he’d just shut up and shake his head and say: “Where’d I go wrong?” or “Who is this guy anyway?” He knew he could get caught up in the work and in the moment, and he would never compromise the take or the music or the project. But he’d often take himself to task, take a short break and a mental reset, and then come back – a little sheepishly – and hit things twice as hard. He knew that, from time to time, the person most likely to get in the way of moving things forward was Jimmy Buffett, and he always kept an eye out for times when he thought he was getting too full of himself or ahead of the game. 3 Never expect to get what you give. Not everyone’s heart is as big as yours. I’m not sure that Jimmy ever got enough credit for his charitable work – not just the music appearances at all the big-deal group events over the years – but the gestures and the sleeves-rolled-up time he devoted quietly to a number of causes, people, and charities that were personally near and dear to his heart. But, unsurprisingly, not everyone else in these ventures lived up to their end of the bargain, delivered on their promises, or even showed up when they said they would. What was completely amazing to me was how he never let these disappointments get him down, interfere with what he needed to do, or even break his belief that most of the people out there were solid citizens, well-intentioned, generous, and willing to help others in need. It would have been so easy to get angry, to hold a grudge, or to say, along with The Who, “We won’t get fooled again,” and walk away. But he never did. He didn’t measure, he didn’t compete, he didn’t lose his faith, and he never stopped giving back. He did everything he could, never expected anything in return, and never tried to impose his contributions and commitments on others. There’s never a best way to say goodbye or to close a piece like this, but I’m sure that Jimmy wouldn’t mind if I take a line from Now and Forever, which Carole King wrote in 1992:
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