Four Ways To Fail

I often use Jimmy Buffett as an example of what’s possible even if you’re not the most talented, tallest, best connected, or smartest person in the room—because early on, Jimmy was none of those things. Most know the Jimmy Buffett who is one of the most successful musicians, authors, and entrepreneurs of the past 25 years and is worth $600 million dollars. But there’s another side to this story with some important life lessons. Here’s four ways to fail, and how Jimmy Buffett beat the odds.

1. Party All The Time. It would be easy to assume that a man who made millions from selling and promoting Margaritaville, had a hit song about day drinking (“It’s Five O’clock Somewhere), and seemingly lives a life of leisure would love to party. The truth is Jimmy Buffett lives a healthy lifestyle and rarely drinks. There’s no way he would have the long-term success he has if he were a heavy drinker or drug user. Moderation (or abstention) is the key to dealing with vices that can drag you down and derail your career and your life.


2. We Don’t Need No Education. It may surprise you to learn that Jimmy Buffett graduated from the University of Southern Mississippi, and was a member of a fraternity. (It was also in college that he met the person that would teach him how to play guitar.) Formal education is very important, but so is informal education and being a lifelong learner—which Buffett is. He’s a voracious reader, became a pilot later in life, and took voice lessons for years. Throughout his career Buffett has been a genius at being ahead of trends, teaming up with others, and taking advantage of opportunities. Early on he found sponsors to help finance his tours, was one of the first to have his own radio internet station, and teamed up with others to help build an empire around the Margaritaville brand.


3. Make Excuses. Jimmy Buffet grew up in Mobile, Alabama. His parents were both involved with the shipping industry, and he and his sister grew up in a middle-class neighborhood. He had zero connections in the music industry growing up. It was his decision to write for Billboard magazine that helped him meet important people in the music business and helped him get his start. He didn’t use his lack of money as an excuse, but found places to play, record an album, and eventually travel to Florida (and Key West) despite being broke. Jimmy Buffett is not tall by any means. He's not known for being a particular strong singer or good guitar player. He would often introduce a fictitious band when he didn’t have one. He didn’t make excuses, he made it happen.


4. Be a Quitter. This will sound like a country song, but it’s all true. Jimmy Buffett was married and divorced by the time he was 25 years-old. His first album sold less than 500 copies, and the tapes for his second recording were lost. He played for tips in New Orleans, the Chart Room Bar in Key West, and at Steak and Ale restaurants where nobody showed up—but he didn’t give up. Instead, he started small. It took five albums and a slowly growing fan base before Margaritaville become a hit in 1977. He started a small clothing line and promoted it through his newsletter. His first retail store was a little shop on Duvall Street in Key West. His first book was a children’s book he co-wrote with his daughter. You only fail when you stop trying.




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Copyright © 2021 by Lee Silber