Western Swing Music Legend, Ray Benson on Living the Dream

Photo by Wyatt McSpaddin

Any one of us can fantasize about becoming the next X, Y or Z, whether it’s Steve Jobs, Justin Bieber or Julia Child. Well, of course, we all have dreams of spending our days engaged in what we’re passionate about. But how do you do it?

Writing our book, we had the chance to speak to dozens of extraordinary people who are doing just that—living their dreams. When we talked to Ray Benson, leader of the Austin-based, nine-time Grammy award winning Western Swing band, Asleep At The Wheel, about what it takes to keep the dream of playing music alive for over 40 years he told us:

“My uncle played saxophone on cruise ships. Everyone said it was a wonderful hobby that wouldn’t pay so he gave it up. But I was stubborn because I had the dream.”

Although Benson’s passion is playing music, he’s clear-eyed about the music industry:

“This business chews you up, burns you out and spits you out. I’ve seen it a hundred times but I’m not going to be one of those people.”

He told us about a time in the 80’s when his bus broke down on the side of the road in the middle of nowhere and needed $400 in repairs. Benson had no family, he felt professionally underappreciated and he was $100,000 in debt to the government. “It was the low point,” Benson said. “Disco was happening and we were not.” But Benson pushed through. And his single-mindedness of what it takes to realize his dream of succeeding in the music industry can be applied to any other endeavor that requires years of dedication and the stamina to overcome obstacles both internal and external:

“I tell anyone who asks if it’s been worth it, ‘Can you do anything else? If so, do that. If you can’t be happy unless you’re a working musician performing every night than this is what you’ve got to do.’”

It’s a sobering thought that you’d have to sacrifice so much for your dreams, but it’s one that we heard echoed by many other people in our book. If they felt there was something else they could have done and been happy, they wouldn’t have taken the hard road. But like, Benson, they were stubborn and made the choice to pursue their dreams.

For your listening pleasure: Asleep At The Wheel with a few guest stars including Willie Nelson, Merle Haggard, Reba McEntire, Vince Gill, Dwight Yoakam, the Dixie Chicks, Lyle Lovett, Johnny Gimble and Manhattan Transfer.

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