On January 3, 2014, Andrew Proctor, the Canadian-born, 42-year-old leader of Literary Arts, Portland’s flagship bookish nonprofit, sat down for lunch at the downtown restaurant South Park. One of his several dining companions was Michele Wasson, a lawyer specializing in estate planning who also chaired the board of Wordstock, an annual two-day festival known for attracting some of the world’s most famous writers to Portland.

Wasson wanted to know: would Proctor be interested in taking over Wordstock?

The question itself was pretty much the only simple thing about the prospect. Wordstock was beloved by Portland’s core literary scene but beset by money, venue, and organizational problems. Literary Arts, which Proctor has steered to ever-larger audiences (and more audacious fundraising goals) since taking the helm in 2009, already had plenty to do: running the city’s highest-profile lecture series, for instance, and gearing up for a major capital campaign. But on November 7, Proctor will unveil a reimagined Wordstock: a single day, teeming with writers local and national, at the Portland Art Museum. The “new” Wordstock aims to solve the problems of its earlier iteration and, beyond that, establish itself as an annual rendezvous between Portland’s readers and the publishing industry’s hottest, smartest prospects.

“I think we’ve created a festival that has a wide range of writers in it, for a wide range of people in terms of age and tastes,” Proctor says.

A decade earlier, a new Portland literary festival was just gearing up, the work of Larry Colton, a former pro baseball player turned writer. Colton hoped Wordstock would help fund a writing-oriented teacher-training program. Instead, in its launch year, 2005, the festival lost about $100,000.

But it did attract some major names: John Irving, Norman Mailer, Sarah Vowell, and Alice Sebol in that first year; Gore Vidal, Jennifer Egan, and Dave Eggers in the years that followed. As it evolved, Wordstock shifted from using multiple venues to become a full weekend at the Oregon Convention Center, its expansion and ambition apparently unstoppable.

But as Wordstock grew, so did the complications. The convention center space was costly. Funding proved elusive and, come 2008, the economy went into free fall. “I’m going to blame it all on Dick Cheney and George Bush,” says Colton. “When the economy tanked, the money wasn’t there.” In the months after the 2013 festival, the cracks were showing. Two executive directors left in quick succession. Talk of a move to Portland State led nowhere. The festival had announced the ever-ominous year off. And Andrew Proctor was taken to lunch.

“It was a pretty fun process to do the thought experiment,” Proctor says now. “What would change the picture? How would we make it work?” One thing was clear: if they took on the festival, Literary Arts would need some heavy-hitting partners. Proctor called Portland Art Museum director Brian Ferriso, casually inquiring if he could “borrow” PAM. With that yes in his pocket, Proctor turned to Powell’s Books owner Emily Powell. Once the giant indie bookstore signed on as Word-stock’s bookseller, Proctor knew he had the makings of a festival.

Still, he wasn’t hesitant to make changes. Proctor trimmed the event down to a single day, moved it to November, and planned a food-cart invasion to signal “the end of the convention center hot dog.” He also needed money. A trio of the region’s biggest philanthropic players—the Miller Foundation, the Meyer Memorial Trust, and the Murdock Trust—agreed to provide foundational funding to the tune of $400,000 for the festival’s first three years. The next step was to find a festival director.

Thirty-one-year-old Amanda Bullock, who had run programming for New York bookstore Housing Works, stepped into the role on January 5 of this year—a year and two days after Wordstock popped the question to Proctor. Bullock was tasked with picking writers and planning the events. In September, she announced a lineup that includes Jon Krakauer, Maggie Nelson, and John Irving, back 10 years after he first graced a Wordstock stage.

Bullock says she’s aiming the festival at readers—from the casual to the obsessive—and feels Portland is the right place to host such authors. “There are so many great writers and great stories in Portland,” she says. “I think it would surprise people if Portland didn’t have a book festival. It just seems like a natural fit.” Whether people will throw down hard cash to prove it is the question: $15 for entrance, $5 of which can be redeemed on a book purchase.

“Up until November 7 at midnight, we will have done nothing but pretty steep high-altitude climbing, with a fair amount of reputational risk attached,” says Proctor. What does success look like? “I would like to see at least 2,500 people going through that door.” But he adds that the festival’s long-term sustainability won’t be clear until years three and four, when the foundations’ funding dips and the festival will be looking for new funders to replace it. “Will we be successful in building that cadre?” Proctor wonders. “Does the festival feel urgent and needed to the community? Those are the real questions. In some ways it’s a referendum on whether Portland wants a literary festival in town or not.”

On November 7, readers of Portland, you can have your say.