Ron Sexsmith plays the Myer Horowitz Theatre tonight. (Supplied photo)

Don’t feel too sorry for singer-songwriter Ron Sexsmith.

Oh sure, we understand the inclination, especially since the 42-year-old troubadour has spent the last two decades spinning crafty, laconic pop songs that frequently indulge his melancholy, to put it mildly.

But in person, Sexsmith is upbeat, affable and downright chatty, especially on the topic of how he’s often misinterpreted by fans and critics as being on some sort of perpetual downer.

“Sometimes I’ll see articles that have this ‘poor Ron’ quality to them, and I don’t want to be perceived that way,” says Sexsmith, who plays Burton Cummings Theatre this Saturday in support of his latest disc Time Being. “My girlfriend is always telling me to think positively. I don’t think I’m a negative person, but I am hard on myself.”

He’s especially critical when it comes to his music, which over the span of 20 years has seen him evolve from a folk circuit busker to an indie-world darling to a celebrated songwriter namechecked by folks like Paul McCartney, Elvis Costello and Elton John.

For his most recent album, he once again joined forces with producer Mitchell Froom (Suzanne Vega, Los Lobos), with whom he’d collaborated frequently in the 1990s.

“I pull my hair out over the smallest details, so I really have to work on it until it feels right,” Sexsmith says of his creative process. “I’m proud of every song I’ve ever written, but they’re all flawed in some way. But they do represent what I was doing at that time.”

He describes Time Being as his “crossroads” album, a product inspired by the process of looking back on his life, and of coming face to face with his impending old age.

“These days, 40 is the crossroads, and it seemed really surreal to me to be going to funerals for people who were the same age as me,” he explains. “It tends to make you reflect on your own life, so yeah, mortality kind of worked its way into the mix.”

Of course, reflecting on your advancing years often leads to taking stock of your current fortune, and Sexsmith is similarly candid about the financial success that continues to elude him no matter how well his albums are written up by critics and contemporaries the world over.

As an example, he cites the fact his debut disc was released on the same day as Alanis Morissette’s first album. And though both were well-received, they were the starting points for two incredibly different careers.

“Hers went ‘Pow!’ and mine kind of struggled,” he says. “I don’t expect that kind of success, and I don’t have any desire to be rich. I just want to get to a place where I have a nest egg of some kind.”

Sexsmith is just as blasé about the current crop of singer-songwriters — think Damien Rice, David Gray and Josh Ritter — whose career paths he helped launch, but whose ranks he’s never really joined.

“I know that I missed the singer-songwriter boat,” he says. “But I would like to think I made it cool to do that again.”

Tickets to Sexsmith’s show are $27.50 at Ticketmaster (www.ticketmaster.ca or 780-3333), or at the West End Cultural Centre.