Colbie Caillat Brings a New Sound to an Old Favorite in Acoustic Video for 'Try' (Exclusive)

Colbie Caillat lives right down the street from Sheryl Crow. 

“I’m always asking her for advice,” Caillat, 38, tells PEOPLE in a recent interview about the fellow Grammy-winning singer/songwriter. “We talk about life, and she lets me know where she's at and her life wisdom, and in doing so, she makes me feel more OK about the places where I'm at.”

Caillat pauses for a moment to let the circumstances swirling around her mind remain unsaid. 

“Sometimes, you feel like you're going to be in a different place in your life at a certain time, and it's not always the case,” continues Caillat, who moved to Nashville seven years ago. “Sheryl is always just giving me the advice and tools for how to move forward with that.”

And while these two singer/songwriters have certainly created a bond personally, they also have now continued their already successful professional bonded, with Crow appearing on Caillat’s brand new album Along the Way.  

“I've been a fan of Sheryl for my entire life, and I got to tour with her about 10 years ago, which was the biggest honor,” explains Caillat, whose acoustic video for her reimagined platinum hit song “Try” premieres exclusively on PEOPLE.  “And now to call her a friend and have a song with her?”

Making Caillat’s current situation even more surreal is the fact that she recorded the uplifting “I’ll Be Here” with Crow in her very own home studio, located just about 10 minutes outside of Nashville.

“It was a pinch me moment,” Caillat remembers of the recording of the song she wrote alongside Brett James, Jason Reeves and Kenny Edmonds. “Sheryl's vocal is so calming and just so nostalgic. It was so perfect for this song, and she's just so raw, down to earth, and real. There's no frills. It's just who she is in the most beautiful way.” 

Certainly, Caillat herself has also exuded her share of sunshine both personally and professionally via hit songs such as “Bubbly,” “Realize,” and "Lucky," her Grammy-winning duet with Jason Mraz.

“I like to write [songs] in an optimistic way,” Caillat explains. “I think anything that can help you through the hard times is a good thing.”

Indeed, Caillat’s debut country album Along the Way is one that comes on the heels of heartbreak. “This is a more loving, appreciative breakup album,” Caillat chuckles. “Some of the songs [on this album] felt sad in a way, but also I felt like I had learned so much from these relationships that I really wanted to share.”

And sharing those songs seemed easier coming from a new angle.

“It wasn't like I intentionally said, ‘I need to write within a different format,” says Caillat of her swerve into country music. “I just felt like writing from this new mindset of these life experiences. I also wanted to touch on the fact that being lost is OK. It's normal. I think we're just so used to thinking everything's a fairytale and everything is permanent.”

Indeed, Caillat found herself wondering what was next after a recent relationship fell through, leaving her to write songs such as “Meant for Me.”

“People in your life can be meant for you for a short amount of time, and that's OK,” Caillat says of the emotional backbone of the song she wrote alongside AJ Pruis and Liz Rose. “I'm in this state of mind where I realize that things come and go and I'm going to be OK with it.”

Granted, there are slivers of anger in certain pieces of Along the Way, especially in the opening lyrics of “Still Gonna Miss You.”

“That’s me giving a little jab,” snickers Caillat of the song she wrote alongside fellow songwriter Jason Reeves.

But for Caillat, time has healed the wounds. Perhaps, where she stands today can be best heard on the album’s opening track “Wide Open.” 

“You can feel the heartbreak and loss, and I think you can be content where you are being on your own,” says Caillat of the song she wrote alongside Alysa Vanderheym and Jordyn Shellhart. “I also think you can be hopeful for what's to come."

She pauses. "I see a lot of people say, ‘This is what I'm going to do’ or ‘I'm going to have children at this age,’ and you just learn that's not always the case. Life might have a different plan for you.”