Jake Owen Reflects on Career, Reveals the One Thing He’d Do Differently

Owen shares an honest look back at his journey in country music.

By

Lauren Jo Black

| Posted on

July 8, 2025

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11:10 am

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Jake Owen; Photo Provided

Jake Owen is looking back on his journey through country music and opening up about the one thing he’d change if he could do it all over again.

After a golf injury sidelined his original career path, Owen left Florida State University just nine credits shy of graduating and moved to Nashville in 2005. He quickly began writing songs, landed a publishing deal, and soon after, signed with RCA. By 2006, his debut single “Yee Haw” was making waves on country radio.

Jake Owen; Photo Provided
Jake Owen; Photo Provided

Since then, Owen has scored 10 No.1 singles, earned gold and platinum certifications, toured with legends like Alan Jackson, Keith Urban, and Kenny Chesney, and amassed over 2.5 billion streams in the U.S. alone.

Now, as he prepares to release a new album this fall, with the lead single, “Dreams to Dream,” out this Friday, Owen took part in an Instagram Q&A where he shared a personal revelation.

“Probably not be as hot headed as I once was,” he admitted. “I came to town (Nashville) excited, alone, scared, and full of dreams. It’s a town of people wayyyyy more talented than you/ I will ever be. I wanted to prove that I was worthy of being here. I think my insecurities came across as arrogance and I hate that.”

He continued with a candid message of growth: “I know my worth. I know my value. There’s just a way of doing it with grace, and I can’t say I always did that” 

In a recent interview with Country Now ahead of his Country Thunder Florida set, Owen reflected on his early days in Nashville and the lesson that stuck with him most: “No one will ever believe in you as much as you believe in yourself.” 

Jake Owen; Photo Provided
Jake Owen; Photo Provided

“So when I think back about the last 22 years, if there’s anything I’m proud of, I’m proud that I made that move,” he continued. “I’m proud that I got out of Florida and took the risk to make it because if I hadn’t have done that, I don’t know that this would’ve ever happened. So take a chance.”

In recent years, Owen has done a lot of self-reflection. In September 2021, a moment he describes as “embarrassing” led him to quit drinking. Now nearly four years sober, he says it’s “the best decision” he’s ever made.

“I feel better than I have ever felt in my life,” he wrote. “I’m finally REALLY living.” 

Jake Owen launched the Driftwood Rambler Tour earlier this summer. The trek is set to continue through August 29 in Du Quoin, IL.

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Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.