The trait extends to every facet of his position as head coach of Kentucky basketball, including his team's style of play. Some coaches find offensive and defensive systems and stand by them no matter the circumstances, but not Calipari.
His schedule, though, is hectic to say the least. If he's not on the road recruiting, he's spending time with his family or his team. If he's not coaching practice or a game, he's at a speaking engagement or advocating for a charitable cause.
Where then does he find the time to innovate?
"He's in a lot of planes," junior guard Jon Hood said at media day on Thursday.
This is Hood's fourth year under Calipari and he's noticed a trend. Whenever Coach Cal travels by air, he seems to come up with something new.
"He always seems to come back to us with, 'I was thinking about you while I was on the plane and this is what I thought,' " Hood said. "Every off day he'll go recruiting and he'll come back, say we have an off day Wednesday, he'll come back that Thursday with, 'Well, we're going to put this in now or we're going to change this.' "
In the estimation of Hood, Coach Cal's willingness to change is among his best - and most underrated - attributes.
Hood can remember when Calipari arrived in Lexington. Outside of his reputation as a recruiter, the buzz was about Coach Cal's vaunted dribble-drive motion offense, the style of play that unleashed Derrick Rose and Tyreke Evans.
"Everybody thought, 'Oh, we're going to have this great new offense that we're going to run nonstop and that's just going to be the entire game is all this dribble drive stuff,' " Hood said.
Three-and-a-half years later, the dribble drive is still in many ways synonymous with Calipari. But in reality the Wildcats have deployed a more traditional attack, with pick and rolls, dribble handoffs and even post-ups.
"My freshman year we ran up and down the court and then at times we'd throw it into DeMarcus (Cousins) and let DeMarcus be DeMarcus," Hood said. "He's an animal, he always will be an animal and Patrick (Patterson) as well."
Even so, Coach Cal uses the dribble drive to great effect, even when his teams don't use it extensively in games. It's among the first things taught in early-season practices.
"All that does is teach you how to play basketball," Hood said. "That's it. You can't play in a system or run plays without knowing how to play basketball."
Just as importantly, the installation of the dribble drive gives Calipari a chance to learn about his team and get an accurate appraisal of its strengths and weaknesses. From there, he begins to shape a game plan around the Cats' strengths, whether it's Cousins in the post, Brandon Knight as a shooter or Marquis Teague in the pick and roll.
The strange thing is that he hasn't always been that way.
While most people fall into a routine as they age, Coach Cal is the opposite. He recalls his first few years as a head coach at Massachusetts. At that point, his basketball strategy was nothing more than a melting pot combining the things he had learned as a player and assistant.
"When I was at UMass, I'm going to be honest with you, five of those years, I had exactly the same lesson plan," Calipari said. "We were going to play, and we won a lot of games and day lot of good, kids did good, but we could have done better. I could have coached better."
Twenty-five years into his career as a head coach, Calipari is quite different. As he prepares to coach a team that returns just one major contributor from the group that won a national championship in 2011-12 (Kyle Wiltjer), he has an idea of how things are going to start, but little beyond that.
"The beginning will be the same, but after we get started we'll probably do more scrimmaging this year than I did a year ago earlier," Calipari said. "But normally I'll have four to five practices already planned. I've got two, and those are in pencil, let me put it that way."
Coach Cal is keeping his eraser at the ready because it's impossible to know exactly what he's going to see out of his team once the Cats can practice 20 hours a week beginning with Big Blue Madness on Friday. If Jon Hood is right, the changes Coach Cal implements in the coming months will start on airplanes.
The reason they'll likely work is also because of the work he does in between those flights. Calipari recruits players who are willing to change with him.
"Whatever I ask our guys to do, they'll do it," Calipari said. "I just have to make sure whatever I ask them is the right thing."
Volleyball seeking attendance record in Madness kickoff
Before the men's and women's basketball teams hold their first open practice opportunities of the season at Big Blue Madness, the Kentucky volleyball team will take the floor for its first-ever match in Rupp Arena. The Wildcats will take on Mississippi State at 5 p.m. with doors opening at 4 p.m. hoping to break the national volleyball attendance record of 17,340 set at the 2008 Final Four.
For Craig Skinner, playing in front of a crowd that large would be a dream come true, one that started when Skinner was introduced as UK head coach before a basketball game in Rupp in 2005.
"Obviously Midnight Madness is about basketball, but for us and our players to have a chance to compete in front of as many people as we hope will show up tomorrow (is special)," Skinner said.
The volleyball and basketball teams are accustomed to sharing facilities, as all three squads practice at the Joe Craft Center. The close proximity has helped breed friendships between student-athletes, so the basketball Cats know what the event will mean to their volleyball-playing counterparts.
"That's definitely real cool for their program," junior guard Jarrod Polson said. "They're really good so I definitely think it's going to be fun for them. They're really hyped about getting to play in front of so many people."