Alexandra Kay Reveals Her Near Rock-Bottom Moment — And What Saved Her Music Career

Alexandra Kay was dangerously close to quitting music for good. After a Netflix show fell through and her second label deal collapsed, she found herself back home in Illinois, questioning everything and feeling like a failure. On the latest episode of Artist Friendly with Joel Madden, she opens up about that difficult chapter, the songs and people that pulled her through, and the journey that inspired her sophomore album, Second Wind.

Each night on stage, Kay tells the story of hitting the lowest point in her career and feeling ready to give up. Back in 2018, she appeared in a reality series called Westside, which followed her and nine other aspiring singers in Los Angeles. When the show didn’t pan out and her label dropped her shortly after, she returned to Illinois, struggling to find the momentum or funds to survive in Nashville.

“I remember right when I had gotten back in Illinois, I was loading my dishwasher and talking to my mom on the phone, and I was driving four and a half hours back and forth to Nashville writing songs at this time, but I couldn’t afford to put myself up in a hotel or anything. So I would just couch surf and then go home if I didn’t have anywhere to stay.”

A trip to Nashville just before hitting that point of rock bottom resulted in her penning four songs she “really loved”. She decided to release them independently as a last-ditch effort to try and gain some traction.

“I was telling my mom on the phone, I said, ‘I just wrote these four songs and I really like ’em, and I’m just going to put ’em out independently. And if this doesn’t work out, I’ll probably just see what else God has in store for me. I just don’t know that I can take another letdown having just lost my second deal and a show that was supposed to change my life that flopped and broke and I have nothing.’ And I kind of [had] that guilt from going back to my hometown after you had just moved to LA and did this whole Netflix thing and felt like a failure.”

The first independent release from this batch was titled “I Kinda Don’t.” It became her first song to not only go viral, but also to launch straight to the top of the iTunes charts. Her second release ended up having the same outcome, suddenly causing labels in town to pay attention to her.

“Before I knew it, all the labels were in my inbox and I haven’t slowed down since.”

Kay proudly shares this part of her story on stage every night because it’s a reminder of how far she’s come. It also shines a light on the deep meaning behind her sophomore album, Second Wind. The project builds on the emotional depth of her debut All I’ve Ever Known but offers a brighter, more hopeful tone, as she reflects on major life changes including moving past her divorce, falling in love again, and signing with BBR Music Group/BMG Nashville.

“It was all the times that I thought I was done that the fans were like, you are not even close to being done. And they were my second wind. So that’s why, [I] named the record, ‘Second Wind.’”

It was during the conversations surrounding the project and learning to trust again, thanks to her new boyfriend and guitar player, Rocko, that she realized the title perfectly captured her journey.

“The song ‘Second Wind,’ we wrote about kind of just how he revitalized me in this whole, me being completely broken and not trusting anybody…And then he just put the wind back in my sails. And so that’s what we wrote ‘Second Wind’ about.”

That sense of renewal and rediscovery didn’t just shape the songs on Second Wind, it also gave Kay a new perspective on her entire musical journey. Looking back, she feels grateful for every step along the way, from the smallest struggles to the biggest milestones, knowing they all led her to tour with country music superstars and the chance to finally send her first song to country radio.

“I am so grateful for all of the little bitty things that I did because when I went on tour with Jelly Roll and I was standing on stage in front of an arena with his arm wrapped around me as he’s like telling everybody ‘she’s going to be huge’ and blah, blah, blah, I felt so, so grateful for every little bitty dive bar show I played the first tour I ever booked,” she explained.

“Me and a small an independent agent booked the whole thing ourselves, and half the places weren’t even paying me because not enough people showed up. And I was playing four hours for the three drunk people that were there and then my car blew up because I was driving my Buick to all of these cities. I think of those times. And I’m like, thank God, I’m so grateful for literally everything.”

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Alexandra Kay’s single “Straight For Heart” is officially playing across the airwaves after impacting country radio in November of 2025. She earned 71 adds in its first week making her one of the biggest solo female debuts ever on country radio.

Plus, in 2026 she will open for acts like Cody Johnson and make her way Down Under for dates across New Zealand and Australia in support of Old Dominion, all while continuing to make her rounds to radio stations across the U.S.