The question is: How does Bentley repeat that previous success? After nine albums (with work underway on a 10th), what can there be left to say that isn’t a repeated sentiment, thinly rephrased to sound like a new thought? How can the excitement of recording for the first time be recaptured? The answer, at least to Bentley, is to accept that you don’t have the answer.
“When I go into albums, I try to really embrace the idea of ‘I don’t know,’” says Bentley. “I try not to be afraid of just saying, ‘I don’t know.’ And let there be insecurities, let there be doubts, question myself. I never want to go in there and just do what I do. I don’t know what that even is.
"There’s a lot of great songwriters in Nashville, and once you get to a certain level, you get songs pitched to you, and could just work with the same producer, and cut the same songs, and probably make a pretty good record. But for me, every record has to be a real exploration of myself, and where I am at this point in my life.”
Finding a fresh perspective, or even a moment of reflective peace, can be difficult with Bentley’s schedule. His normal day can include landing in a new city, doing up to three different shows, all while making sure crew members have what they need in between performances. For Bentley, the moments to unwind, to decompress and find clarity come in the form of flying his own plane.
Flying solo in his own private plane has been Bentley's preferred mode of transportation since he successfully got his pilot’s license in 1997. By working out an arrangement with Cirrus Aircrafts, the country artist always has a set of wings at his disposal, which he takes advantage of at every opportunity.
“I love it,” Bentley says of his pastime. “Being up there alone. Got some XM Radio, put The Highway on, or sometimes turn it off and just listen to nothing but the propeller beating against the wind. I really enjoy that a lot.”
“I love it ... Being up there alone. Got some XM Radio, put The Highway on, or sometimes turn it off and just listen to nothing but the propeller beating against the wind. I really enjoy that a lot.” — Dierks Bentley
Another solace for Bentley as he travels are his wife and three children, who from time to time accompany him on the road. Bentley speaks with pride about the involvement of his two daughters and son as he plays for fans. The youngest, his 5-year-old boy, Knox, dances on the stage alongside his dad during the show, high-fiving audience members with bottomless energy. When Bentley and his band play as their alter ego band, Hot Country Nights, his daughter Jordan dresses up as a miniature version of Bentley and sings "Old Town Road," while oldest daughter, Evie, will frequently come onstage to sing on “Travelin' Light,” during his main stage show for the day.
“Children are the great leveler," Bentley says. "They can knock you right off of whatever platform you’re on. My kids, they love the road. I mean, I’ve talked to them before about, ‘Hey, do you want me to kind of pull back a little bit, slow it down, spend more time at home?’ And it’s, ‘No way, Dad. We love the bus, we love the road, you can never quit. You can never quit.’”
And by all accounts, Bentley shows no signs of quitting anytime soon. He continues because he takes into consideration the need for balance in his life. For every moment surrounded by people on the ground, there is quiet peace thousands of miles in the air. For every ego-inflating moment onstage adored by screaming fans, there is his bloodline, an arm reach away, to ground him back to reality. For every comfort provided by a show that worked perfectly, there is excitement, and success, in the new.
“Last year was really the beginning of this tour in a way, because this tour is all based off the album The Mountain, so a lot of big pieces are still in play as far as chunks of the set list and some of the production," he says. "Of course, we spend a lot of time revamping to make it feel new. New for the crowd, and also new for us.”