Alan Jackson may have sold more than 50 million albums, garnered over 100 awards and have a star on the Hollywood Walk of Fame, but the country sensation says when it comes to his family -- which includes wife Denise and daughters Mattie, Ali and Dani -- he deals with life issues just like any other guy. And in spite of his epic fame and fortune, right now one of his most pressing issues is watching his daughters grow up and gain their independence.

Twenty-year old Mattie is Alan's first born and recently got her very own place. The experience, Alan admits, is bittersweet. "She just moved into an apartment and started cooking food and we had to buy her cooking utensils, and it's like she's a little adult now," Alan boasts to Nashville's Tennessean newspaper. "It's amazing."

The family, who until recently called their sprawling 135-acre estate named Sweetbriar home, were in for a rude awakening when they first eased her out of their nest and into her college dorm a couple years ago. Buying what they felt were necessities for her home-away-from-home, the proud parents used a trailer to haul her new possessions to college, where they realized they were ill-prepared for her new surroundings.

"It was tiny and looked like a jail cell," he recalls. "She had so much stuff it wouldn't even fit in a room. We started carrying it in and the people that had lived in the dorm for a year or two were laughing, saying 'What are you going to do with all of that?' We had to take half of it home."

The Grammy winner released his 18th studio album, 'Freight Train,' earlier this year, and says he couldn't help but draw inspiration from Mattie's experience when he was writing songs for the album. "'After 17' is a song I wrote when [Mattie] went to college so that's kind of where I'm at in that part of my life," Alan tells The Boot. "If you listen to that song and knew anything about me, you'd say, 'Oh yeah, he wrote that about his daughter,' but I try not to write them that they are so specific that they wouldn't apply to anybody that has a child."

Selling Sweetbriar earlier this year and moving into a smaller house while they have yet another home built, the proud father thought the experience of moving would be hard on his daughters, but he was pleasantly surprised at how easily they adapted. "I think that's what I was so crushed about, 'Oh my gosh, we're going to sell the girls' home place,'" he says. "But, they were ready to go. They used to ride golf carts all over the property. They weren't like boys who would have been out there fishing. But that's what I was worried about. They're all fired up about (designing their new rooms), so I don't feel so bad about it now."

Alan's latest single, 'As She Walks Away,' is a duet with the Zac Brown Band. Calling up that favor was an easy choice for Alan. "I've been a fan of their writing and singing and the fact that they are a real band and real musicians and they play on their records," Alan says. "They're just good guys, and we're both from Georgia."

In addition to 'Freight Train,' Alan is also releasing a double-disc set of all his hits, '34 Number Ones,' on November 23. He recently announced his fall tour dates, along with opening acts Chris Young and the Band Perry. Find dates here.