November 07, 2013 01:00 PM

Dierks Bentley

Dierks Bentley and his wife Cassidy have put together a new parenting plan: divide and conquer!

Since welcoming their third child, son Knox in October, the country crooner admits everyone — including daughters Jordan Catherine, 2½, and Evalyn Day, 5 — is still learning to adjust to being a family of five.

“My wife and I are definitely out-manned for sure. It requires you splitting up and doing things separately,” Bentley, 37, told PEOPLE at his Miles and Music for Kids event in Nashville on Sunday.

“I took the girls to breakfast this morning. It’s kind of a drag because we hate being apart, but that’s just the way it is right now.”

But while bringing another baby into the mix has been a “big transition,” a laid-back Bentley is going with the family’s flow. “One kid changes your whole life. Two is crazy. [With] three you already know what to do so you don’t stress the little things so much,” he says.

“With my two girls, I was afraid every second they were going to fall down and cut themselves. This time I’ll be a little more, ‘It’s okay, you’re fine!'”

Bentley’s new approach to parenting doesn’t just apply to the hands-on aspect of daddy duty. Despite it being four weeks since their son’s arrival, the proud parents are still wrapping up some unfinished business on baby boy’s birth certificate.

“My wife and I liked the name [Knox]. It’s simple — my name’s one syllable. It just popped up and we stuck with it,” Bentley explains. “We’re working on the middle name — still working on it. We turned the paperwork in as just Knox Bentley, but soon enough … “

One thing that has taken priority in the singer’s life is instilling a sense of appreciation in his children. Bentley, who was on hand to lead a pack of more than 1,000 bikers during the eighth annual charity ride, planned to present the check to the Monroe Carell Jr. Children’s Hospital at Vanderbilt with his two daughters by his side.

“I want them to grow up to be great people, to always be conscious of the environment around them and to serve in some way,” he shares.

He jokingly adds, “Hopefully this is one of my better examples they’ll pick up on — there’s plenty of bad examples of things I do for them to grab onto, but hopefully they’ll remember this.”

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— Anya Leon with reporting by Katie Kauss

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