The country star opens up to PEOPLE about raising his 16-year-old daughter Bailee

Jelly Roll was just 14 when he was first arrested – but he’s not worried his teenage daughter Bailee will make the same mistakes.

In this week’s cover story, the Grammy-nominated singer, 39, tells PEOPLE about the conversations he has with daughter Bailee, 16, and recalls a recent conversation in which he reminded her how much potential he has sees in her.

“(I said), ‘I’m not judging you because of what you do. I judge you based on what I think you’re capable of,” he recalls. “‘You’re so much smarter than I was at 16. You’re so much better, so much more emotionally intelligent. You can read a room so much better. So don’t try to talk your way out of trouble, Miss Sassy, ​​by weaponizing my past.’”

Jelly, who is also father to 8-year-old son Noah, says Bailee is “completely further along” than he was as a teenager and he is confident she has a bright future.

Related: Jelly Roll Says Some People Are ‘Mad’ About His Success Because He Has Exhibited ‘Crazy, Narcissistic, Selfish’ Behavior in the Past (Exclusive)

“When I look at what she does, which I think is terrible, I look back at what I did when I was 16 and I think, ‘Oh man…’ If I’m hard on her about things or a little pushy am, she “I know it comes from love,” he says.

The “Winning Streak” singer and his wife Bunnie

He and his daughter remain close, and she was by his side when he performed at the 2024 CMA Awards earlier this month. Jelly was behind bars when Bailee was born and said her birth was a turning point in his life.

“We were very, very close before it blew up, but she understands what it means for her future and the future of the family,” he says. “She’s a really run-down child. She has been in the same public school district for 10 years and has had the same friends since me and Bunnie have had custody of her. I think a lot of that helped.”

Related: Jelly Roll’s Rules for a Sweet Life: Forgiving Your Past Self, Prioritizing Your Marriage, and Raising a “Sassy” Teenager

Bailee recently appeared at Bunnie’s Stupid blonde podcast and revealed that she hopes to attend Columbia University after high school with plans to become a criminal defense attorney.

“I want to go there and study law. As far as music goes, I don’t have any plans right now,” she said.

The teenager also revealed that most of her classmates have moved on from the fact that she has a famous father.

“We’re all kind of used to it,” she said. “He came to football games and stuff. I think everyone’s over that ‘Oh my God’ thing. And besides, people somehow know that I’m not the right guy. Otherwise it’s pretty easy to make new friends, but I just don’t do that anymore.”

For more on Jelly Roll, pick up the latest issue of PEOPLE, on newsstands everywhere now.