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Tax Advice From David Foster Wallace

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As shocking as it sounds, some people deeply love taxes, and David Foster Wallace was among them. After publishing his 1996 novel, Infinite Jest, and winning a MacArthur Foundation grant, Wallace enrolled in three years of advanced tax courses at Illinois State University; his final novel, published after his suicide in 2008, is set in an Illinois IRS office and includes long footnotes about obscure tax provisions and the history of the agency.

“Tax law is like the world’s biggest game of chess with all sorts of weird conundrums about ethics and civics and the consent of the governed built in,” Wallace wrote in an email to his friend, the novelist Jonathan Franzen, in 2007. “For me it’s a bit like math: I have no talent for it but find it still erotically interesting.”

The late novelist’s obsession with taxes is the subject of a new research paper by Arthur Cockfield, a law professor at Queen’s University in Canada, forthcoming in the Pittsburgh Tax Review. The drudgery of taxes is what attracted Wallace to the subject, Cockfield argues. And, he says, Wallace has helpful advice for those of us bogged down by tax season. 

Embrace the chore, boring as it is. The key is “to find the other side of the rote, the picayune, the meaningless, the repetitive, the pointlessly complex,” says a character in Wallace’s last novel, The Pale King. Don’t think of tax preparers as bland pencil pushers. They’re “cowboys of information,” Wallace wrote, who wade into minutiae and come out with useful answers.

Another character, Chris, is a lazy “wastoid” stoner who, while watching a daytime soap, gets inspired to sign up for tax classes. He meets a passionate tax professor and eventually joins the IRS. In many ways, Chris was taking the advice in Wallace’s much-admired 2005 commencement address at Kenyon College: Don’t float through life just trying to entertain yourself, Wallace urged graduates. Instead, “choose what you pay attention to” and “choose how you construct meaning from experience.”

After all, the tedium of tax time has a purpose: Funding a government that all of us rely on in some way. In the 1990s, the IRS tried to become more taxpayer-friendly, treating Americans as “customers” who deserve good service. That troubled Wallace, Cockfield says, because he thought taxpayers should see themselves not as customers but as citizens with a moral obligation to pay taxes. “We abdicate our responsibility to the greater good of the U.S. and expect government to do it,” Wallace wrote in notes. “Government is parent and all the rest of us are greedy children.”

When we’re bored and act spoiled, it’s easier to ignore our civic duty—which includes getting upset about loopholes that make the tax code unfair.

According to a new report, the U.S.’s top 1% received $95 billion in tax subsidies in 2013, more than the bottom 80% combined. But, Cockfield says, “it’s so hard to get political traction on these big tax issues because it’s so spectacularly dull to the public.”

Wallace’s advice on this applies to the rest of adult life: “If you are immune to boredom, there is literally nothing you cannot accomplish.”