It’s hard to believe, given his record-breaking sales and countless accolades, but Kenny Chesney’s career path was not always smooth sailing.
“We all get caught up in the idea of, ‘We want this now,’ and I was no different,” Kenny recalls to Billboard of his anxious early days in the business. “I had a few hit records, and there were other people having hit records and they were getting paid $2500 more than I was getting paid … I remember talking to [my manager] Dale Morris going, ‘Why are we doing this? Why are we doing that? Why isn’t this happening?’ That mentality was one of the reasons that we’re doing what we’re doing today. That taught me patience and that everybody is in this together, and we’re going to take this and make it wonderful and not just live for the moment. Dale called it: ‘We’re betting on what’s to come, not what’s right now.’ And that’s hard. When you’re a kid, you want it all right now.”
Kenny soon channeled his energy into making his live show “something special.” “Whether it worked or whether it didn’t, I was going to do it,” he said. “It wasn’t safe and it wasn’t probably the smartest thing to do, but it was the smartest thing to do for me. I got a taste of the George Strait stadium tours and I was going to do whatever it takes.”
For my complete writeup, visit The Boot.