The summer before Lori Ostlund won the Flannery O’ Connor award for short fiction, she was ready to give up writing. Ostlund was walking through the Sunset District with her wife, Anne Raeff. At the corner of 19th and Taraval, as they waited for the light to change, Ostlund made her decision.
“I am going to quit writing,” she said to Raeff. “And I’m going to go back to school and get a paralegal degree.”
In retrospect, Ostlund would’ve probably returned to writing — eventually. But that summer was a low point for her. Ostlund was worn down by rejections from publishers (a common affliction in writing), and a career in fiction felt unsustainable in an increasingly expensive San Francisco.
So Ostlund, lured by the promise of financial security, enrolled in San Francisco State University’s extension program for paralegal studies in 2008. That semester, in October, Ostlund got a call telling her she had won the Flannery O’Connor award for short fiction, a prestigious honor that’s been publishing some of the best fiction in the industry since 1983.
After that, everything changed. Ostlund ended up quitting the paralegal studies program after that first semester. In 2009, her winning collection of short stories, The Bigness of the World, was published by the University of Georgia (publication is one of the prizes of winning the Flannery O’Connor) and a career in writing seemed a little less bleak.
Ostlund currently lives with Raeff in Ingleside, where writing and teaching writing is her main career.
While Ostlund eventually prevailed from that low point, carving out a name for herself and her work, there’s still no doubt that success stories in San Francisco’s writing world are scarce. But there are ways that writers of all forms — veteran writers with national recognition, full-time writers who manage to work five side-hustles to make ends meet, writers with budding aspirations who carve out pockets of time amid their nine-to-five to scrawl in their notebooks — can make it work. That’s why, in honor of National Novel Writing Month, the SF Weekly spoke to five Bay Area authors and poets on how to make it as a writer in the city.
50,000 Words, 30 Days
National Novel Writing Month changed R.H. Herron’s life. “I have dedicated a couple of books to NaNoWriMo,” Herron says. “I could not have my career without NaNoWriMo.”
NaNoWriMo is one of the biggest time-crunch challenges any novelist can undertake: It requires you to finish 50,000 words toward a book within the month of November.
NaNoWriMo was what pushed Herron to finish her first book, How to Knit a Love Song, which would be published in 2010 — two years after completing her first draft of 50,003 words. Since her first stint with the novel-writing challenge, she’s been an absolute believer in NaNoWriMo, having published 17 books since then. Her latest one, Stolen Things, is a thriller based on her experiences as a 911 dispatcher — one of her day jobs before she became a full-time writer (with a few side hustles) a few years ago in 2016.
“The biggest advice I have is to write as fast as you can, and lower your expectations as low as they can go,” Herron says. “A lot of people get very frustrated by writing, because they have good reading tastes, and they can tell what they have written is not up to that standard. And they get frustrated and quit.”
But Herron points out that you can always revise later. Getting that first draft on paper is the hardest part. Getting the words on paper can require some trickery.
“Writing is about how to manipulate yourself into doing it,” Ingrid Rojas Contreras says. Rojas Contreras is a University of San Francisco professor and the author of Fruit of the Drunken Tree. For her, writing always starts with the color blue.
Wearing royal blue in whatever form — a royal blue silk slip, royal blue pajamas — is her way of trying to get her mind to associate that specific hue with writing. Rojas Contreras actually has five writing outfits dedicated to this, and she won’t let herself wear royal blue anytime else. “My body starts to not be able to resist,” she says about her writing color. Wearing blue is about creating discipline, and discipline is key to finishing any work.
Jason Bayani, a poet and the artistic director of Asian American arts group Kearny Street Workshop, knows this well.
“People look for a particular type of magic to [writing]. And it’s not [magic],” Bayani says. “Yes, there’s a lot that’s magical in the act of creation. But at the end of the day, to get there is work. And you have to treat it like that. You have to treat it as a practice — something you keep going at.”
So how do you make sure you don’t burn out? Some people recommend writing 1,667 words a day, but Kevin Dublin, an operations manager at the Writing Salon, has a different strategy. He recommends using the archplot — a specific story design that some call the “classic” structure — or some outline and then setting writing goals not based on word count, but on plot points.
“You can break it down into chunks,” Dublin says. That way the work, and the process of making it, will be more dynamic.
After all, at the end of the day, it still has to be fun. And if it isn’t — that has to change.
“Throw your plans out the window if they seem at all boring to you, and start jotting down really exciting ideas,” Herron says. “Surprise yourself on the page. The more excited we are to write a scene, the faster we write it.”
Surviving as a Writer in the City
If you ask a writer in the city where they live, they might have a similar answer: “I used to live in San Francisco, but I moved out to X, Y, or Z.” That’s because San Francisco is not an affordable city. It’s a place where one-person households making six-figures can casually refer to themselves as “poor” or “broke,” and people will agree with them without a second thought. Or even without a first thought about how San Francisco is one of the worst cities in the nation for wealth inequality, a devastating fact for the city’s artists who work in fields that can’t rake in $100,000 starting salaries.
“A lot of us are still living below the median,” Bayani says. “Yeah, we can survive, but what does that do for options like having a family, or buying a house?”
At the start of 2019, The New York Times published an article asking “Does It Pay to Be a Writer?” and the answer was very obviously, no. The Authors Guild Survey cited showed that full-time book authors in America earned a median income of $20,300. Even writers with successful careers can earn significantly below the poverty line.
“It’s expensive. Even though there’s interest out here, it’s still like — especially for poets — how do you get people to buy books?” Bayani says. “How do you get support in the city?”
Bayani believes that as far as city and grant funding goes, San Francisco still fares better than most cities. Still, many writers have to either work day jobs or numerous side hustles in order to make ends meet.
Rojas Contreras, for instance, used to work five different jobs ranging from teaching to writing to translation. “The sixth job becomes, ‘How do you manage those five jobs?’” she says.
It can be stressful, to say the least. Working another nine-to-five means you might not have the energy — or time — to write. Being a full-time freelance writer means you won’t have the safety of healthcare and a 401(k) from an employer.
“How do we continue being able to produce, and how do we figure out how to live out here?” Bayani asks. “If people just can’t afford living here, what does that do to the arts scene?”
On an individual level, there aren’t too many easy solutions. There are fellowships and scholarships for those with financial need at different San Francisco writing institutions, like The Ruby, The Writers Grotto, and The Writing Salon. With that financial aid, these organizations can offer classes, mentorship, writing spaces, and more for free or at a significantly reduced cost.
It can be useful for growing as a writer, but for day-to-day survival, Ostlund recommends finding work with healthcare.
“Teaching high school is probably one of the best things for a writer to do,” Ostlund says. One, because like most jobs, it offers healthcare. Two, because Ostlund believes that teaching draws upon the same creative energy and spontaneity used in writing. That’s what her wife does, and together they’re able to benefit from Raeff’s healthcare.
Ostlund also knows that the stress of a daily nine-to-five can be taxing when you also need to generate work afterwards. That’s why writers might want to consider part-time work, if it’s sustainable enough financially.
“It’s harder financially, but it’s easier in every other way,” Ostlund says. “Psychologically, emotionally, and certainly in terms of writing.”
Despite all the difficulties, San Francisco still boasts a long literary history, and a vibrant arts scene. On a Sunday afternoon in the comfort of his living room, Dublin hosted an informal writing salon (different from The Writing Salon, where he works), setting out plates of DIY lunchables (crackers with cheddar cheese and circles of ham) and handing out elderflower seltzers with stainless steel straws. This salon doubled as Dublin’s informal Andrew Yang campaign fundraiser, though not everyone there had an opinion on the 2020 presidential candidate.
The snacks were a hit, and about 15 or so writers passed around wine and talked about the chapbooks they were working on, climate change, their cats, and their day jobs before the reading started. People took turns sharing their work (a poem on LGBTQ+ identity and asylum; a children’s book on inclusion and kindness) and cheered for one another. Dublin introduced each writer before they went on “stage,” a section of carpet in front of his bay windows, framed with a string of fairy lights.
The goal was to bring writers together. Community, Dublin emphasizes, is integral to writing. That’s one of his biggest pieces of advice for anyone trying to make it as a writer in the city.
“Connect and get a feel for the community. Participate in it. Don’t go into it and go, ‘Oh this is something I want to get,’” Dublin says. “Contribute to it.”
It’s hard to imagine writing as a group activity, but it actually relies on community in more ways than one.
“So much of writing is an isolating practice, but it can’t entirely be that,” Bayani says. “You still need other people, at the very least for support.” If anything, you just need someone to complain about writing to. Or someone to keep you accountable — especially if you’re trying to accomplish a month-long challenge like NaNoWriMo.
“There’s something about writing with other people that turns on your competitive streak,” Herron says, who recommends going to cafes with fellow writers, and encouraging each other to produce work.
San Francisco has a plethora of writing spaces: The Writing Salon, The Writers Grotto, The Ruby, Kearny Street Workshop, Quiet Lightning, the SF Creative Writing Institute, Litquake, ZYZZYVA, etc. But you don’t have to sign up for recurring classes or pay membership fees in order to find a writing community of your own. For Rojas Contreras, it’s important to create “the culture you want to be in.” “You don’t always need an institution to create,” she says.
Sometimes it can be just as easy as getting a group of people together. Sometimes being a writer in San Francisco can be as simple as picking up your pen and starting to write.