Kenny Chesney Is ‘Terrified’ of ‘Failure’ in Country Music Career

(Cindy Ord/Getty Images)

Kenny Chesney might be hailed as one of the “top-selling country performers,” but despite his success, the singer has admitted he is still “terrified” of failure.

Chesney made the confession during an appearance on “Sunday Sitdown with Willie Geist” while discussing his music career and journey from performing for enchiladas in a college bar during his early days.

“I’m terrified of being complacent, you know, and failure,” Chesney told Geist, according to Today. “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.”

Chesney added he wanted to be “grateful” for his road to success.

“And just reflect on all the years that it took to get to this spot,” he said. “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 goin’ to get close to connecting with these people I got to have their perspective.”

Chesney also spoke about how he got into music while studying marketing at East Tennessee State University. His mother gave him a guitar for Christmas at the time.

“I was the kid in college sitting in a corner with a tip jar,” he said. “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.”

After graduating, Chesney moved to Nashville and landed his first record deal in 1993.

The songs from his first five albums gained significant traction, leading to the release of a greatest hits album in 2000. However, Chesney added that even after countless tours and album releases, including his latest one, “Born,” he still feels like he’s back in college strumming for enchiladas.

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