Songfacts®:

• Bentley wrote "Lot Of Leavin' Left To Do" on his tour bus with fellow country singer and friend Deric Ruttan and songwriter Brett Beavers. The song is about Dierks being on the road and having a hard time with relationships. The line, "Lovin' me might be a long shot gamble, so before ya go and turn me on, be sure you can turn me loose, cause I still got a lot of leavin' left to do," is a warning to any potential love interest that you shouldn't fall for him because he is on the road 300 days a year.
• This song is in the "outlaw" country style exemplified by Waylon Jennings and Merle Haggard.
• The song, which became a defining track early in Bentley's career, almost had a completely different storyline - at least in co-writer Deric Ruttan's mind.
  
  Ruttan jotted down the title in his notes, initially imagining it as a ballad about a woman leaving. "This is a testament to the power of collaborating," he told The Tennessean. "I had thought it was like, 'She's got a lot of leaving left to do,' you know, from her perspective. But I shared that with the two of them, and they were like, 'No, I think it's the guy who's leaving.'"
  
  That shift in perspective shaped the song's identity. Brett Beavers noted that it perfectly captured Bentley's life at the time - young, single, and constantly on the move. "It's not that he's a bad guy or a rogue," Beavers explained. "It's just that women wanted to tie him down, and he was more like a tumbleweed."
  
  Given Bentley's love for Waylon Jennings, they decided to inject some of that outlaw grit into the track. "We thought, 'Let's take a chance and get some of that Waylon feel,' and it all kind of came together."
• Ruttan recalled how the song first took shape. He and Beavers were in the front lounge of the bus, strumming an idea on the ganjo - a six-string banjo tuned like a guitar - while Bentley was lying in his bunk. "I can still remember seeing his hand on that bunk curtain, and suddenly it flies open. He leans out like, 'What is that?'"
  
  Ruttan remembered Beavers turned to Bentley and said, "Your next hit, dude. Get out here and rock with us."
• Many of the lyrics were pulled straight from Bentley's real life. The line, "These old boots still got a lot of ground" was a direct reflection of his well-worn footwear and his rambling lifestyle.
  
  "You could just look at him and pull lyrics out of it," Beavers said. "He wore old boots, so we were just writing his life."