Kenny Chesney Reflects On Fearless Journey To Country Music Stardom: “I Had No Plan B”

“I truly loved what I was doing, and I believed in my heart that one day, that I would see where it would take me,” Chesney shared.

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Andrew Wendowski

Andrew Wendowski is the Founder and CEO of Music Mayhem. As a 29-year-old entrepreneur, he oversees content as the Editor-In-Chief for the independent brand. Wendowski, who splits time between Philadelphia, Penn., and Nashville, Tenn., has an extensive background in multimedia. Before launching Music Mayhem in 2014, he worked as a highly sought-after photojournalist and tour photographer, collaborating with such labels as Interscope Records and Republic Records. He has captured photos of some of the biggest names, including Taylor Swift, Metallica, Harry Styles, P!NK, Morgan Wallen, Carrie Underwood, The Rolling Stones, Madonna, Shania Twain, and hundreds more. Wendowski’s photos and freelance work have appeared nationwide and can be seen everywhere from ad campaigns to various publications, including Billboard and Rolling Stone. When Wendowski isn’t running Music Mayhem, he enjoys spending time at concerts, traveling, and capturing photos.

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Posted on January 14, 2024

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Kenny Chesney; Photo Courtesy of Rick Diamond

Kenny Chesney recently appeared on the podcast Connective Tissue with John C. McGinley, participating in a wide-ranging conversation about all aspects of his decades-long career. Looking back on his early days in the music industry before becoming one of the biggest country stars of his generation, Chesney revealed that he had no backup plan when it came to his goals in life.

Chesney Never Had A “Plan B” When Chasing Country Music Stardom

“What sustained me early, especially in those first couple of records — when it wasn’t a very popular thing to do, to play my records at that point — what sustained me was that I had no Plan B,” Chesney shared. “I truly loved what I was doing, and I believed in my heart that one day, that I would see where it would take me.”

The singer’s first album, 1994’s In My Wildest Dreams, didn’t produce a Top 40 single, and it was another several years and singles before Kenny Chesney scored his first No. 1 with “She’s Got It All” in 1997.  “Each time that I got to a different place where I felt like that I was making headway, I looked at that as a building block,” he recalled. “And I looked at that as validation that I’m on the right path.”

Three decades into his career, Chesney has sold over 30 million albums worldwide and earned 32 No. 1 singles at country radio. He continually embarks on massive stadium tours and has been named the CMA Entertainer of the Year four times and ACM Entertainer of the year four times, in addition to numerous other accolades.

Gratitude Is An Important Part Of Chesney’s Journey

From his early days to now, gratitude is also an important part of Chesney’s worldview, with McGinley telling Chesney that it’s clear he is just as happy to be on stage as his fans are to see him.

“The way you connect the connective tissue between you and 60,000 people is that you’re just as thrilled that they’re here as they are that they’re with you,” he said. “And that resonates. It pops.”

Kenny Chesney agreed that “you can’t fake it,” adding that he doesn’t think “you can have the amount of gratitude you’re talking about without a lot of struggle.”

Kenny Chesney; Photo by Andrew Wendowski
Kenny Chesney; Photo by Andrew Wendowski

The East Tennessee Native Hates It When People Ask Him For Advice On “How To Make It?”

When people ask him for advice now on how to “make it,” a question he admittedly hates, “this inner voice in my head is going, ‘This guy’s never going to make it because you don’t do it to make it.’”

The Tennessee native connected this notion to the fact that he had no plan B, explaining, “You do this because you just can’t help it. That’s why you do this. You don’t do it to make it.”

“You watch too much of The Voice. You’ve watched too much American Idol,” he continued. “So you do this because you just can’t help it. And I think it’s hard to have a lot of gratitude when it’s given to you. Now, if you’ve had years of struggle, then you’re going to have some gratitude in your life.”

Kenny Chesney; Photo Courtesy of Allister Ann
Kenny Chesney; Photo Courtesy of Allister Ann

Kenny Chesney further reflected on social media’s impact on society, acknowledging that while of course people are struggling, “it’s a different struggle, it seems.” “If you go through a lot of struggle, especially when you’re trying to be a creative person or do what you’ve done, Johnny, with your life, starting from below zero and getting to a place where you can actually make your life work, doing what you love, like you said, it puts you in a position to live in gratitude.”

This year, Chesney will visit fans on his Sun Goes Down Tour, which begins in April with support from Zac Brown Band, Megan Moroney and Uncle Kracker.

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Andrew Wendowski is the Founder and CEO of Music Mayhem. As a 29-year-old entrepreneur, he oversees content as the Editor-In-Chief for the independent brand. Wendowski, who splits time between Philadelphia, Penn., and Nashville, Tenn., has an extensive background in multimedia. Before launching Music Mayhem in 2014, he worked as a highly sought-after photojournalist and tour photographer, collaborating with such labels as Interscope Records and Republic Records. He has captured photos of some of the biggest names, including Taylor Swift, Metallica, Harry Styles, P!NK, Morgan Wallen, Carrie Underwood, The Rolling Stones, Madonna, Shania Twain, and hundreds more. Wendowski’s photos and freelance work have appeared nationwide and can be seen everywhere from ad campaigns to various publications, including Billboard and Rolling Stone. When Wendowski isn’t running Music Mayhem, he enjoys spending time at concerts, traveling, and capturing photos.

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