It never hurts to look ahead, something that Sam Outlaw has been doing ever since he bailed on a lucrative full-time advertising job to pursue a career as a retro-minded country singer.

Reached in a van that’s headed to San Diego as part of a West Coast tour, the fantastically quotable Los Angeles transplant says he’s hard at work on a number of different projects. One of them is getting ready for a baby, as his wife is pregnant with their first child.

Figuring that it’s better to be focusing on a follow-up to last year’s critically lauded Angeleno before he winds up on diaper duty, Outlaw’s been busy in the studio. He notes that his as-yet-untitled sophomore album is close to being done, and that folks can look forward to him mixing things up some. Where Angeleno is heavily indebted to the California-country sound pioneered by genre giants like the Flying Burrito Brothers, his next outing will expand his sonic palette.

“It’s going to be similar in that there will still be the traditional, grounded country songs—it’s not like I’m abandoning those,” Outlaw says. “But I think it’s going to have a little more exploration. Some of my favourite music is ’70s singer-songwriter stuff. James Taylor is just as much an influence on the music I love as Ray Benson. I love Bread, America, and that whole vibe.

“Even the Christopher Cross and Peter Cetera soft-rock shit that a lot of people make fun of is some of my favourite music. It’s the music that was probably being played when a lot of people of my generation were being conceived. And I think there’s a reason a lot of people were having sex to it.”

For now, though, Outlaw—that’s his late mother’s maiden name—is busy supporting Angeleno. After getting off to a gorgeous start with the mariachi-flavoured “Who Do You Think You Are?”, the album operates as a love letter to a California scene that’s inspired everyone from the Long Ryders to Uncle Tupelo to Ryan Adams.

Outlaw cleverly nods to country’s golden-’60s era with “I’m Not Jealous” and “Jesus Take the Wheel (And Drive Me to a Bar)”, settles in at the quiet end of the tavern with “Love Her for a While” and “Old Fashioned”, and nods to a painful family past with the dramatic “Ghost Town”. Beautiful little touches abound, from sundown steel guitar to south-of-the-border horns.

Before strapping on the guitar full-time, he was making a decidedly more lucrative living in advertising. But at age 30, obsessed with the likes of Gram Parsons, Don Williams, and Dwight Yoakam, and tired of doing things half-assed, he decided to go all-in on music, something that still terrifies him today.

Helping quiet those voices has been the fact that Outlaw is running with a heavy-hitting crowd, with big boosters including My Morning Jacket keyboardist Bo Kuster, who plays keys on Angeleno, and Ry Cooder, who coproduced the album.

“I had the songs ready to go, and had a good idea what I wanted the record to look and sound like,” he says. “But trying to find a country-music producer in L.A. and to go into the studio and find musicians who understand what the music should sound like was definitely tough. There are a handful of musicians who know who the Flying Burrito Brothers were and have the whole California-country thing in their back pocket, but it’s tricky trying to get the sound. When Ry Cooder came onboard, it made a huge difference, not just for his great guitar work, but because he had a real idea what the songs were supposed to sound like.”

Cooder also acted as a valuable sounding board, which was important, considering that in many ways the whole business of making music was new to Outlaw. And terrifying.

“There are days when I’m performing a show and getting a good vibe from the crowd where I’m like, ‘This is all going to work out great because I was totally meant to be a singer,’ ” Outlaw says with a laugh. “Then, most every other day, I wake up with a voice in my head going, ‘You’re never going to make it and you’re a total loser.’ ”

Sam Outlaw plays the Cobalt on Saturday (February 27).