Before releasing her Along the Way album in 2023, Colbie Caillat had recorded as a solo artist before, but it had been a while — seven or eight years, by her count.

In the 2000s and 2010s, Caillat was a solo pop singer-songwriter. She released a handful of albums during that time, netting hits like her chart-topping 2007 single, “Bubbly.”

She’s always had some country crossover — she duetted with Taylor Swift in 2008, long before Swift’s transition into pop — but forayed even more deeply into the country realm with the formation of her band, Gone West, in 2018. That group consisted of two couples: Country songwriter Jason Reeves and former JaneDear Girls member Nelly Joy, plus Caillat and her then-fiancé Justin Young. But after Caillat and Young ended their ten-year relationship in April 2020, the group dissolved shortly thereafter.

Now, as she ventures out on her own again, Caillat’s in the uncommon position of knowing what both solo success and a group dynamic feel like. During a November 2023 conversation with Taste of Country, Caillat explained the pros and cons of both.

“I really wanted to work with my friends and be in a band. I feel like you get to go through all that stuff with people — all the highs, all the lows,” she explained, remembering what it felt like when she first formed Gone West.

But making Along the Way as a solo artist had some major perks, too. “It’s a little simpler. It can be a lot of cooks in the kitchen [when you’re in a band],” Caillat acknowledges.

That’s especially true since she made the record, as she was healing from a major breakup. After she and Young ended their engagement, she slowly began writing songs — some of which were so personal and true to her heartbreak that she had to wait three more years until she had healed enough to release and promote the album.

Now, looking back, she says she’s proud that so much of this album was a solo endeavor.

“On this album I wrote three songs by myself and I was so proud of that, because I usually end up writing with people. I started every song on this album [by myself], but I finished three of them by myself, and I love them,” Caillat explains.

“They’re super honest and real of what I’ve gone through in this breakup,” she elaborates. “I feel like because I’m back to being a solo artist, I was able to write these songs by myself.”