Thomas Rhett has checked a handful of goals off his bucket list, but becoming a pilot is not one of them.

For nearly five years, the country crooner has been contemplating whether or not to get a pilot's license. The ambitious dream is more than achievable for Rhett, as he comes from a family with a long line of aviators.

The hitmaker previously caught up (Jan. 9) with Big Machine Label Group to discuss why he has pressed pause on pursuing the venture.

"I could definitely see me still wantin' to do that," said Rhett referring to the challenging hobby. "I have so many pilots in my family. My brother-in-law Grayson is a pilot, my father-in-law is a pilot, a lot of my close friends are pilots."

Rhett declared that he wants to work on himself and build more courage before chasing the pipedream.

"I think it would take a little more trust on my own end to trust that I could do it right. I'm not the most attention-to-detail person, and I feel like you really need to be detailed to be a pilot," the vocalist admitted. "So, I don't know. Maybe I'll become a very detail-oriented person over the next five years and decide that gettin' my pilot's license is something I'd wanna do."

He continued to poke fun at Dierks Bentley, who received his pilot's license in 1997. The chart-topping artist previously told E! News that his savvy skill tends to come in handy while out on tour, as he flies himself "back and forth" from shows.

"If Dierks can do it, I can do it," Rhett pointed out.

Initially, Rhett wanted to pick up the pastime with Florida Georgia Line's Tyler Hubbard. With safety on top of their mind, the two did not schedule any long-distance trips.

"Me and Tyler Hubbard have been talking about doing it together, but real easy stuff, like just flying around Nashville," he shared in 2017. "I don't think I would ever want to fly myself to a show or anything like that, but just real chill flying."

Similar to Rhett, Hubbard never followed through with their plan. However, the platinum-selling artist proposed to his wife, Hayley Stommel, in a helicopter.

A tight-knit group of country hitmakers has earned the title – Bentley, Kris Kristofferson, Jimmy Buffett, Tim McGraw, Chris Janson and most recently, Dustin Lynch.

Until Rhett brings his talents to new heights, he is slated to embark on his headlining Home Team Tour 23 in early May alongside Cole Swindell and Nate Smith.

"Being on the road is one of my favorite places to be," shared Rhett. "I can't wait to see the joy on y'alls faces next year and with my buddies Cole Swindell and Nate Smith. We're definitely gonna have a good time."