Kenny Chesney is ‘terrified’ of ‘failure’ 30 years into his country music career

Kenny Chesney will never get too comfortable.

On the most recent episode of the "Sunday Sitdown with Willie Geist" podcast, the illustrious country music star told the host that his life still feels like it did before fame 30 years ago, just with a little more pressure.

"I’m terrified of being complacent, you know, and failure," he explained. "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."

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The "She's Got It All" singer is gearing up for his Sun Goes Down 2024 Tour, which debuts at Tampa’s Raymond James Stadium on April 20.

"I want to be grateful for what’s happened," Kenny continued. "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 to 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."

Chesney explained to Geist that having that outlook is what has kept him humble throughout his impressive country music career.

"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," he said.

During Kenny's appearance on "Sunday Sitdown," he spoke about how his life has changed since he got started singing for enchiladas at a college bar. Chesney said he was studying marketing at East Tennessee State University when his mother gifted him a guitar.

"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," Chesney said.

He added, "Free enchiladas."

After college graduation, Chesney moved to Nashville and in 1993, he signed his first record deal.

"I swear, man, in ways I still feel like I’m doing the same thing, I just got a lot more stuff around me," Chesney said of his career today. "You know, the interaction is still the same, but it’s just with a lot more people."

Variety reported in January 2022 that the country music crooner has sold more than 30 million albums and is considered one of the "top-selling country performers," netting more than $1 billion in touring since 1995.