Colbie Caillat’s Breakup Album ‘Along the Way’ Redefines Heartbreak with Positivity—“It Was Something I Needed to Say”

For most people, a breakup is a time to grieve. It’s a time to bury your head in your pillow and not come back up until every tear you have is cried out. Many songs have been made for such an occasion, and they seldom could be described as “upbeat.” Colbie Caillat, though, has decided to add an element of positivity to her latest record, Along the Way – despite describing it as a “breakup record.”

If anyone could be expected to infuse a little “c’est la vie” into such a situation, it’s Caillat. Right from the beginning of her career, she set herself apart from her peers with an easy-breezy musicality, imported from the sunny shores of Malibu. Listening to Caillat’s catalog is like holding a conch shell up to your ear. You can hear the ocean, smell the saltwater, and feel the warm air. She has an energy about her—one that makes it almost impossible to imagine her down in the dumps. She couldn’t help but make a record like Along the Way. Her warm demeanor demands to break through. 

That’s not to say Caillat isn’t deeply emotional on this record—she’s just hiding it well. 

In fact, Caillat is possibly the most vulnerable she’s ever been on Along the Way. The songs are honest, well-crafted, and referential to her public life. Many of the songs she alludes to being inspired by her split with ex-fiance, Justin Young, whom she dated for 10 years and frequently collaborated with. On all of them, she is markedly candid. 

Caillat previewed the album with a song that captures the entire methodology of the record, “Worth It.” I know it wasn’t perfect / But loving you was worth it / There’s still sweetness in the memories / Even after all the hurting, she sings.

“I cherish that relationship,” she tells American Songwriter of the optimism of “Worth It.” “I loved the time that we shared together.” It’s less of a post-mortem of Caillat’s former relationship and more of an homage. If most breakup songs are a mournful funeral, “Worth It” is a celebration of life. The rest of the album follows in that same vein. 

“It’s a breakup album in a very beautiful, optimistic way,” Caillat says. “I feel like my perspective shifted. I really wanted the whole tone of this album to be how things can end and then begin again. You learn from those relationships, it’s not always a bad thing, and you see the beauty in it.

“That’s what I felt about this relationship, and I really wanted people to have an outlet for that,” she adds. “Upset breakup songs are important, but these are very loving ones.”

Caillat started the writing sessions for what would become Along the Way in 2020. A lot of things were rushing at her at once: the shutdown of the world, her personal break-up, and the break-up of her country outfit Gone West (a quartet formed in 2018 composed of Caillat, Justin Young, Nelly Joy, and Jason Reeves). “It was this really interesting time for all of that to happen at once,” she says. 

It took Caillat a while to digest everything. When she did, she started to put her revelations down on paper with the help of co-writers Liz Rose, AJ Pruis, Jason Reeves, Kenny Edmonds, Alysa Vanderheym, Jordan Shellhart, and Brett James. Together, they created an environment that allowed Caillat the space to be vulnerable. “I find it more comfortable to be vulnerable in those situations,” Caillat says. “[Instead] of talking to friends or having small talk with people. I feel like I can’t just open up and be vulnerable. 

“When you’re there to write, it’s almost like a therapy session,” she continues. “Most of the time, everyone relates to the same things —we’ve all experienced something similar. [Then that makes] the listener feel like ‘Oh my God, I’ve been through that too.’ It’s the coolest feeling.” 

One of the most accessible songs on the album is “Pretend.” It speaks to many fantasy-driven minds that often spend more time hoping for the future or reminiscing about the past than being planted in the present. In Caillat’s case, she’s dreaming of an alternate reality, in which she and her partner never broke up.

“I’m pretty sure we’ve all done that before,” Caillat says. “[‘Pretend’] was the best reaction that we had from friends listening to the record early on. It also set the tone for what I wanted people to know about this album.” Let’s pretend you opened up / Pretend I didn’t shut down / ‘Cause I can’t pretend that it don’t hurt / And that I don’t miss you now, Caillat sings.

Caillat ventured into the country world with her band Gone West in 2018. Though her music wasn’t that far off to begin with, it was still a career evolution for Caillat—one that she wants to continue exploring. “I didn’t grow up listening to country music, but it’s something that I’ve been slowly influenced by living here in Nashville,” she says. “I just found so much appreciation for it. It felt like a natural fit.”

In place of Caillat’s usual accouterments—beachy guitar riffs and drawn-out vocals—are driving rhythms and classic two-part harmonies. It doesn’t live worlds away from what Caillat is known for, but it certainly accounts for the 2,000 miles between Malibu and Nashville. 

With her new country sound established, Caillat has leaned more into the storytelling aspect of songwriting. “[When I first started writing songs] I was just saying what I was feeling,” she says. “I was inexperienced, I was [more focused] on what rhymed or flowed. Now, I know what I want to say with these songs. I want to be very specific.

“What I did differently with this album is before I went into any session, I had an idea of what I wanted to express,” she says. “Then, I would go into the room and they would help me bring it to life. But, on a few of the songs, I really felt like I could complete them on my own. It was something I needed to say, personally.”

Caillat, who penned three songs on the record by herself, “Blue,” “Two Birds,” and “Old and New,” is her most focused and precise on these tracks. They act as evidence of her growth as a songwriter over the years since making her debut.

“Songwriting is so therapeutic, and you get to really share what you’re going through,” Caillat says. “I try and let everything come in. Then I sit with it. Then I feel good about opening up and writing about it.”

If Caillat can be said to have done anything on this record, it’s open up, using the project as a therapy session—a tool in her healing process—and giving the listener a glimpse into every milestone she hit along the way. The new offering is Caillat’s moment of truth, and the truth has never been so easy to hear. 

Photo by Patrick Tracy