Before he released his 2011 solo debut, Provider, he thought he was done with his musician days: He’d settled in Guelph, worked in community radio, and was content raising a family. It was a new life for the Constantines vocalist, but, as he explains, he liked it.

“There was no plan for that record,” he says over coffee in Toronto’s Liberty Village district. “Before Provider, I was going through a big life change. When that record came together, there was no plan—Jeff [McMurrich, of Idée Fixe Records] asked me if I had any songs. So we tried to make something, and if it was decent, we’d make a few hundred copies of it. There was no pressure. It didn’t matter if people paid any attention to it.”

But people did: Though he’d never admit it, Webb, thanks to his work with the recently reunited Constantines, is one of Canada’s most cherished songwriters. And so, he was pulled back into action, and what began as an innocuous project—he was writing songs for his then-newborn son, Asa—snowballed into something much larger. He travelled as far as Transylvania on the strength of his solo work. He spent a stint opening for Feist. And eventually, it led to his wonderful sophomore LP, Free Will, which was released in May—an album that, for better or for worse, has largely been overshadowed by the buzz surrounding the reformation of the Cons.

As cherished as his former band is, Webb’s making major artistic strides with Free Will—even if it doesn’t possess the rhythmic bombast of the Constantines. Like Provider, Free Will is largely a record about, and for, his son Asa. But unlike his 2011 effort, which basked in the wonder of parenthood, Free Will documents his son’s growth. “The reason I write, and the reason I put things out, is for my son, Asa,” he says. “He’s three now, and in the last year or so, we’ve been watching him discover his agency in the world, his free will.

“He’s feeling out what the possibilities of what that is, what he has control over, what he doesn’t, and there’s great conflict in that. While you want to encourage him to be a responsible, respectful human being, every time I see him make a ridiculous decision that I’d never ever make, I get excited and inspired. I enjoy it a lot.”

There’s a sense that Webb enjoys working solo, too. Free Will‘s songs are less of a bold artistic statement, and more of a personal exploration—evidently, Webb uses songwriting as a lens to understand the world and, by extension, adulthood, parenthood, and work. Webb agrees, and, he adds, watching his son interact with the world forced him to examine his own values.

“There’s less idealism on this record and more analysis. After watching what [Asa] picks up, I try to be more critical of myself,” says Webb, adding that independent radio like Terra Informa, Democracy Now, and GroundWire have aided his thought process. “So in the last three years, I’ve been more critical to what I put out into the world. I’m trying to do more to acknowledge the ways I embody privilege, and I’ve been trying to engage in the world to counteract it.”

And he engages with the world in a different way than he did as a Constantine—especially when it comes to work, a long-running theme in Webb’s lyrics. While his labour-centric songs (like, say, “Working Full Time” or “Hotline Operator”) were often pulsing with fascination, a song like “Someplace I’m Supposed to Be” has a distinctly different tone. “I have a lot of respect for the way people work, how people manage to survive and sustain themselves,” says Webb. “A long time ago, Bobby [Matador, of Oneida] gave me Working, by Studs Terkel, and that’s been a huge influence for years.

“In a lot of Cons songs, we expressly wrote about particular jobs, or friends surviving in interesting ways. It was a joke we had for a long time—that I was vicariously living through my working friends, because I was a full-time musician, and it was a very nebulous and strange way of living.”

But now, Webb’s joined the workforce—even if he’s still negotiating what that means. “I’m engaged more actively in standard, day-to-day jobs,” he says. “There’s part of me that resents the idea of being in one place every day. I took to the lifestyle of a musician, where you’re in a different place every day. But now, with a child and family, there’s this home life I really love. I’m incredibly lucky to have it.”