In 1972, Willie Nelson was 39 years old and essentially finished in the music industry.
At that point, he’d mostly been known as a songwriter. A very good songwriter, he’d written several songs that are now established in the country music canon: “Hello Walls,” “Funny How Time Slips Away,” and perhaps most famously, “Crazy,” which became Patsy Cline’s signature song.
After several years as a famous-among-dozens songwriter, he’d tried his hand at singing his own songs. The results were very mixed. He’d managed to float some songs into the top 25, but unlike Conway Twitty or Loretta Lynn or Dolly Parton, he just couldn’t break out. By 1972, RCA was ready to drop him, and he was ready to saddle up and leave Nashville.
And so he did. He moved to Austin, and we never heard from him again. The end.
Now, we know that wasn’t the end of his career. But look around the tech industry right now — how many people do you know that are still churning away at 40, 50, 60? There are a few, but it’s an industry that likes to ride twentysomethings hard and put them away wet. It likes to lionize young CEOs, even if their immaturity ultimately becomes a boat anchor on the company’s potential. If you haven’t joined management by the time you’re 40, if you haven’t made a substantial impact by the time you’re 40, you may as well saddle up and leave Nashville.
Willie Nelson arrived in Austin in 1972, at a time when the Austin music scene we’ve come to know was just starting to flower. It was mostly centered around a dancehall on the south side of the river called Armadillo World Headquarters. There the music was incredibly eclectic — “hippie” music one night, R&B the next night, then maybe some country mixed in. And into this ferment came a retired country songwriter who embraced the eclecticism and began to transform his musical style. What he produced came to be known as outlaw country.
Three years later, in 1975, “Blue Eyes Crying In The Rain” reached #1 on the country charts and broke into the top 30 on the pop charts. Instead of the slick, violin and pedal steel laden countrypolitan sound of Nashville, it was two guitars, a bass, an accordion, and Willie Nelson.
And with that, Willie Nelson had flipped the script. He’d go on to have another 24 more #1 hits over the next 30 years and become a country music demigod, a Hollywood actor, a global celebrity, and yeah, perhaps the most famous pothead in America.
So maybe that’s the lesson for all of us staring down 40. Don’t stop learning. Don’t stop listening. And don’t stop changing. There’s an entire generation of web professionals that are moving into and through their 40s now, some of whom like Ol’ Willie feeling like it’s time to go to pasture. But soon enough they will find their Armadillo World Headquarters, grow their hair, and turn the web world upside down thanks to their willingness to adapt their experience to the new world.
I hope I’m one of them.