American novelist, Sam Lipsyte, tells Patrick Brzeski why life is one big sell job.

Sam Lipsyte’s novels make you wish reading weren’t such a solitary experience. You laugh, snort or cackle in a quiet café, and looking up in astonishment over the sardonic, profane, yet somehow warm-hearted zinger you’ve just read in finely-wrought elastic prose, you find annoyed eyes, rather than the commiserative twinkle you’ve come to expect from watching the Colbert Report, Curb Your Enthusiasm, or some Lewis C.K. stand-up among friends. Plainly put, political satire and social comedy of this brazen and incisive variety are a rare find in contemporary American literary fiction.

Lipsyte’s third and latest novel, The Ask, centres on the travails of Milo Burke, a failed painter working in the fundraising office of a mediocre liberal arts university. A heartsick cynic, Milo loses his job after upbraiding a self-entitled art student who happens to be the daughter of a university trustee. Marriage failing, grievances all around him, Milo is offered the chance to win back his job if he can secure a large give – the book’s big “ask” – from a wealthy former classmate and friend, who has since become a tech industry billionaire, and happens to have an illegitimate son who’s just returned from Iraq a double amputee and soon becomes entangled in Milo’s quest. Driven by a crazed and perversely brilliant bitterness, Milo excoriates all he encounters, himself included, and in the process points to much of what is wrong with financial-crisis era America. We caught Lipstyle by phone in Seattle, midway through his US west coast book tour, to ask for answers.

At one point in the book, Milo asks a co-worker whether she would like him if he were the protagonist of a novel or movie. And she says, "I would never read a book like that, Milo. I can't think of anyone who would." So, if Milo were a real guy, would you hang out with him?

Well yes, I think I would. My hope, always, is to present characters with the fullest dimensionality possible. So you know, I wanted Milo to be both, likeable and unlikeable, sympathetic and unsympathetic – given each moment, each decision he makes and each thought he has – because I think that’s what we’re like as well.

So you indentify with Milo’s sensibility?

Certainly I have, in my own life, identified with some of Milo’s frustration, some of the anxiety, not so much the full-on bitterness, but some of the ideas behind that bitterness, and the sense of injustice in the world. And well, turkey wraps…

Ah yeah, the turkey wraps. Milo can’t get enough of them. It seemed to us that Milo’s love for turkey wraps was perhaps meant to be read as a metaphor for all the sad little compromises of office life and democratic consumer culture.

I think that’s true, they occupy a strange place in Milo’s imagination about some negative ideas he has about the state of society, but they’re also something he actively devours all the time [laughs].

In the book, almost all of the characters are involved in some sort of sales enterprise. They’re constantly deploying the language of marketing and sales speak on one another at work, but also in their personal lives. What were you driving at?

Well, I wanted to get at how something about our personal relationships and everyday personal dynamics might occasionally mirror this world of sales and advertising and pitching that we all live in. And I wanted the characters to be aware of it. I didn’t want to write a book where the author is aware of these connections but the characters are too blind to see them. So in some ways they use it quite knowingly and even with humour – with a sort of sad broken humour, because they feel stuck in their lives. But the fact is that this is the kind of language that so many people use every day to make a living and it does seep into the way they think about the world and their lives and their loved ones. And you know, everything is a negotiation, everything is some kind of sell job, even if it’s you sort of pitching why you shouldn’t have to do the dishes that night.

Milo once aspired to be a great painter, an artist, but he ends up cajoling for donations from the arrogant rich in the fundraising office of a liberal arts college. It seems that, with Milo’s plight, you’re making a statement about the corrupting influence of big money in the arts in recent years, and the fatuity of notions like “art for art’s sake” these days.

Yeah, there’s absolutely something to that. When I started this book 4 or 5 years ago, I knew he was a stymied painter, and I knew he would have to have another job, and I heard the word ‘ask’ used in the way it’s used in the book, and that galvanised everything for me. There’s not one salient point I’m after, but I wanted to churn up a lot of ideas about art and money and how those things now work in American society. There seemed to be great symmetry with him being this fundraiser, after these disappointments in his own career as an artist.

The Ask paints a pretty bleak picture of the opportunities available to young aspiring people working in the arts and humanities. You’re a creative writing teacher at Columbia. What do you tell your students?

Well, I tell them that there’s no reason not to think that they might someday write a brilliant novel that affects a lot of people and becomes a brilliant movie and gets a wonderful critical reception and connects with a big wide audience. But don’t equate that possibility with security and a steady income. And as long as you can get your brain around that, you’ll be fine.

You know, they used to make the joke, “don’t quit your day job,” because you weren’t talented, right? You do the audition and they say, “don’t quit your day job.” I think the advice today is, you may be the genius of your age, but don’t quit your day job. [Laughs]