Even After 30 Years Of Success Kenny Chesney Is Terrified Of Failure: “I Want To Be Grateful For What’s Happened”

After years of success, “failure” still creeps into the minds of some of the best in the business.

Kenny Chesney knows that he hit the jackpot when it came to his career and that he is luckier than most, but that does not stop him from being worried it could all be pulled out from underneath him. This drive has to do with why he has had thirty years of success in the industry.

On Sunday Sitdown with Willie Geist, Chesney shared his post-sound check routine with the host, which keeps him grounded.

“I’m terrified of being complacent, you know, and failure. We always get into a stadium market on a Friday, and on a Friday after sound check, I’ll go to the very top and sit just by myself.”

After he gets to the top, he reflects on how grateful he is to not only have a crew that helps him get from city to city but also takes time to think about how lucky he is to have fans who will soon fill the stadium’s seats.

“I want to be grateful for what’s happened. And just reflect on all the years that it took to get to this spot. But also, it’s a way for me to emotionally and mentally measure how far it is down here ‘cause I know what it looks like from the stage to up there, but if I’m going to get close to connecting with these people, I got to have their perspective. 

So if you wanna find me on a Friday night, I’m probably sitting up here alone thinking about what I’ve got to do the next night and just taking a moment to reflect and remember how grateful I am to be there.”

Chesney’s humble mentality keeps him on top of his game, and a close relationship with his fans. He reflects later in the interview that he is grateful he has upgraded from singing at local Mexican restaurants while he was in college at East Tennessee State University.

“I was the kid in college sitting in a corner with a tip jar. I played at a Mexican restaurant in Johnson City, Tennessee, called Chucky’s Trading Post, and I played for 15 bucks a night plus whatever I made in tips, which some nights was pretty good on the weekends.

“I swear, man, in ways I still feel like I’m doing the same thing, I just got a lot more stuff around me. You know, the interaction is still the same, but it’s just with a lot more people.”

Chesney is one of those artists whose music and persona convey the message that he is in it for the love of the craft and making something that people can relate to, not the fame. No wonder No Shoes Nation is such a united front.