At the end of an interview that’s touched on everything from self-acceptance and substance abuse to childhood poverty and the horrors of the music business, Hawksley Workman admits he’s been surprised at the amount of ground that’s been covered.

“I don’t know if I knew that I was going to get heavy with you,” says the veteran solo artist, playwright, author, and sometime member of the supergroup Mounties, on the line from a northern Ontario tour stop. “But maybe there’s no other way to get.”

That there’s no shortage of topics to explore is fitting, considering the ground he covers on his latest record, Median Age Wasteland. The release’s 11 tracks find him as at ease with stripped-down acoustic folk (“Snowmobile”) as he is with straight-shooting indie rock (“Lazy”) and strings-laced soft pop (“Skinny Wolf”).

Impressively, he not only has plenty to say, but also understands the importance of putting things in a way that seems effortlessly original. Witness the way Workman tackles the sometimes dangerous game of nostalgia on the drama-drenched “1983”, and how he explores intolerance in a fresh way on the soaring “To Receive”.

Ultimately, what fans will hear is a songwriter who is—as Lana Del Rey might say—fresh out of fucks to give, but in the most positive and liberating of ways. Workman is old enough to remember when a major-label deal was seen as a winning Lotto Max ticket. And he’s now wise enough to know that at a certain point, to keep your sanity, you focus on what you have as opposed to what you don’t.

In his case, that’s the gift of having a long career in an industry where longevity is a rarity.

“There was a moment where I was very pretty and very skinny and very young, and I was on TV at that time,” Workman says, flashing back to an era when MuchMusic made artists instant stars in Canada. “The industry requires you to subject yourself to all kinds of personal scrutiny, because they don’t put funny-looking people on TV. Fastforward to where I’m now sitting at 44 years old and there are certain things that, in order for me to be a happier and healthier, loving husband, musician, and artist, that I’ve had to let go of. That creates space for you to be more of who you really are.”

After launching into an amusing aside about how the music business has always been—dating back to Elvis Presley and the Beatles—about hairstyles, he laughs and recalls how at one point in his past, being a singer with a receding hairline was a full-blown human catastrophe.

“Twenty-plus years in, 17 records, plus Mounties, theatre, and books and whatever, I don’t care about half the shit that I used to care about,” he says.

Translation: Workman is now free to be an artist on whatever terms he sets for himself. That’s markedly different from the part of his life when he rocketed onto the Canadian music scene with 2001’s Universal Records–released (Last Night We Were) The Delicious Wolves. He acknowledges that initial period of infamy did a number on his head, especially after he parted ways with the label.

“The young, disastrous rock star was a role that I was happy to play for a time,” he acknowledges. “I was the guy who could outdrink the record executive in Zurich, Switzerland, and that was really fun and somehow seemed really important at the time. But now I like being brilliant at what I do, and having an affinity for what I do without the booze and the weed. There was three years where I thought about killing myself every day after the conclusion of that record deal. But instead of shutting myself away, I chose to up my output—I made more records and did more touring.”

Median Age Wasteland marks a life change in other ways. After an extended period in rural Ontario—where he owned an idyllic plot of land that included a recording studio—the singer and his wife packed up and relocated to Montreal. There, Workman found himself immediately immersed in and inspired by the city’s famously forward-thinking music scene.

“It was kind of an early retirement out in the country where I built greenhouses and, even though I never did it, learned how to shoot pheasants,” Workman says. “But to be honest, my wife and I ran out of steam a little bit on that life. A friend of mine said, ‘Look, you guys did it, and now you can consult on it.’ ”

Until that time comes, there’s the business of doing what he was born to do.

“I’m a high-school dropout—this is all I’ve ever done and what I’ve spent my entire life doing,” Workman confesses. “I’m riding with the funny character sitting in the sidecar who has this sense that my human value is measured by my work’s value—that’s the thing that inflated the whole balloon.”

And as difficult as that’s been in the past, Workman is okay with it today.

“I get to not care about things because I make a very good living at what I do,” he says. “But that’s taken me 20 years to get to that point. I’ve only just started to trust that my business and my working life is now established to where it’s not going to be blown away by a light breeze. I can wake up, book a show, and think, ‘People will come.’ For most of the last 20 years, it all felt really temporary. But the more I leave the music business proper, the more I realize that I’m now my own entity outside of it.”

Hawksley Workman plays the Imperial on Sunday (November 17).