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Author Don Gillmor.Kevin Van Paassen/The Globe and Mail

When John Updike's Harry (Rabbit) Angstrom was author Don Gillmor's age, after having animated four long, era-defining novels, he had already been dead for three years. Yet Gillmor, 58, riffing on the tragicomedy of his own generation in a Toronto coffee shop, thinks that "we're Rabbit in the third book maybe."

And so all the more fuel for the raging middle-aged anxiety that consumes the hero of Gillmor's Mount Pleasant – also Harry – as he stumbles helplessly toward his own, typically 21st-century senescence, burdened by overinflated expectations, unfulfilled obligations and a fatal taste for the good life.

Most readers will laugh at Gillmor's surgical satire of middle-class mores in contemporary Toronto. He is almost effortlessly funny. But some of us – the Harrys – will also squirm.

Accompanying Harry from the opening page like a character in itself is his crippling personal debt, which buzzes incessantly in Harry's brain like "a high-speed periodontist's drill, a brilliant German instrument that was burrowing in his skull, shrieking as it got closer to his brain." But Harry, being Harry, escapes the noise by tending to the $82 worth of organic lamb he just obtained "from the swarthy criminal at the boutique butcher shop."

The atmosphere in Toronto today is thick with the buzz that torments Harry – the all-pervasive "debt conversation," according to the author. "It just seems to be the zeitgeist," he says, the cry one hears as the first "genuine consumer generation" confronts the limits of its credit-slash-karma.

"We all live more or less outside the boundaries of what we can afford," notes Gillmor, whose mild middle-class demeanour masks a merciless wit. "No one wants the life they can afford." But like Harry, they live it anyway.

"We've anthropomorphized debt," Gillmor says. "It's sort of a close friend we're walking through life with at this point, chatting as we go along."

Harry exemplifies a large but little remarked-upon theme among people his own age, according to Gillmor: "a sense of profound disappointment at a point when they would have expected a profound contentment."

But don't be misled: As sympathetic as he may seem to his hero's dilemma, the author misses no chance to mock him.

Satire is a new turn for Gillmor, but then so is most of what he does. He is diligently versatile, working variously as a magazine and newspaper writer, a children's book author, a historian (co-author of Canada: A People's History), a memoirist and writer of novels, the first of which was Kanata , a sweeping historical saga based on the career of explorer David Thompson.

Gillmor's greatest distinction could be the fact that he hasn't had a steady job since 1982, surviving and indeed thriving since then solely on what his wits could earn, one assignment at a time, without the safety net of a day job, tenured teaching post or wealthy partner. In that, he is an unusually robust specimen of a vanishing species.

"I don't know if I would recommend it," Gillmor says, speaking of the courageous anti-career path he followed. "Everything happened in an ad hoc way." And the landscape itself is so transformed as to be unrecognizable to old pros like him.

"Some people adapt brilliantly, and others less so," he says, adding, "I think I've adapted pretty well."

The circuitous path to Mount Pleasant began with Gillmor's historical writing, which led him to Thompson, who in turn inspired Kanata, the complicated historical sweep of which persuaded the author to do something completely different with his second novel.

"Kanata was a lot to juggle structurally," Gillmor says. "And I thought if I could do something that was contemporary and more contained and linear, it might make this whole process a little easier."

And there's no shortage of material for an open-eyed satirist in Toronto today. "You have all the descriptive material basically sitting outside your window," Gillmor says.

The ridiculous menus, the financial scams, the strivers and the cynics, the great expectations and the ruinous realities: They all buzz merrily through the pages of Mount Pleasant. And in the process, they demonstrate the added virtue of keeping a Canadian master of print fully employed.

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