Big Shoulders, Small Paychecks. Let’s Fix That.

by Sharon Woodhouse

The data is damning, the history is inspiring, and the conversation is overdue.

The time to build an economically vibrant literary eco-system is now.

Carl Sandburg called Chicago “Hog Butcher to the World” and we swaggered to match, didn’t blush. He carved out the city’s identity in blunt, unglamorous terms—slaughter, commerce, labor, muscle—and we put it on ripped T-shirts and screamed it into open mics. Cause in Chicago, we have crafted a mythology around our toughness. The city’s “I Will” spirit means we do hard, gritty things, no standing ovation required.

But mention negotiating writer’s fees, royalty rates, paid speaking events and conferences—or expecting a sustainable income from one’s work at a literary gathering—and suddenly everyone’s moaning and groaning, but-but-butting, excusing, justifying, or taking another gulp of a craft cocktail or PBR while they sort it out.

It’s a contradiction that has been bothering me for almost as long as the 30 years, most in Chicago, I’ve been in book publishing. It’s not just books. It’s all writing. All arts. Chicago’s dynamic and grand and singular creative-creator ecosystem.

The silence, the discomfort, the lack of applied imagination is costing us as a community. A recent Chicago Arts Census* surveyed more than 1,200 arts workers across the city. Sixty percent of them earn less than $40,000 a year—below the city’s average per capita income. Forty-four percent hold graduate degrees. So, nearly half of Chicago’s arts workers have invested in advanced education and are still earning poverty-adjacent income. We know this isn’t a talent problem or an effort problem.

But let’s entertain that it’s not all about outside forces, the economy, oligarchs, structural impediments, undervaluing of the arts, etc. Maybe in part it’s what happens when a community treats money as a subject too crass to discuss. When a community fails to make its own sustainability a priority. When it neglects to use its collective abundance of creativity, imagination, and moxie in service of a vibrant economic ecosystem of our own.

Chicago built its reputation on not flinching—from the Great Fire rebuild to a river reversal, from our trading floors to unscripted truth-telling at Second City—but ask Chicago writers to talk plainly about money and the room goes quiet, gets fidgety, changes the subject, invokes higher principles.

We’re too often immersed in the peculiar idea that discussing the economics of literary pursuits is somehow beneath us, as if all other grownups are entitled to make a living from their talents and passions, but maybe not us. Worse, maybe we think such talk exposes a nakedly commercial soul rather than a purely artistic one. We know better and yet we still fall into romanticizing the frugal, simple-living artist even as we watch talented people leave the field, leave the city, or quietly give up.

We’ve all been in rooms where authors avoid talk of advances and royalties, where they over-explain their need, er, request, for a higher speaking fee. We’ve seen publishers undercharge and literary organizations fold because nobody wanted to have the funding conversation until it was too late.

We have plenty of Chicago precedent for doing it differently.

Harriet Monroe didn’t launch Poetry magazine in 1912 by waiting for the muse. She went door to door, asking Chicago businessmen, gents who probably thought poetry was soft, directly for money. She secured a guarantee of fifty dollars per year for five years from 108 donors before she printed a single page. That is building infrastructure; testing, working, and refining a business model. Poetry magazine is still publishing today over a century later.

The Dil Pickle Club, Chicago’s legendary radical forum that ran from 1914 into the early 1930s, hosted everyone from Emma Goldman to Clarence Darrow, from eloquent, soapboxing hobos to University of Chicago professors in a Near North Side alley. It was bohemian, crazy, and intellectually electric. It was also self-sustaining. You paid a dime to get in. Jack Jones, who ran it, only closed it because of mob extortion and then the Depression.

Studs Terkel knew what he was doing. Forty-five years at WFMT gave him a steady platform and steady income. His books paid too. The Good War won the Pulitzer. Working never went out of print. He didn’t choose between art and income. He built both.

When DNAinfo shut down abruptly in 2017, some of its editors didn’t mourn for long. They launched Block Club Chicago, a nonprofit, reader-funded newsroom from scratch, built a paying membership base now over 20,000 subscribers, and became one of the most respected local news operations in the country. They knew they were facing the headwinds of modern journalism, and they built anyway.

Chicago has been a publishing powerhouse since the mid-1800s. The University of Chicago Press, the largest university press in North America, has been at it since 1890. Rand McNally (1856) constructed a business empire here mapping the world. Scott Foresman (1896), the same, educating generations of schoolchildren with their textbooks. Encyclopedia Britannica (1920, when purchased by Sears & Roebuck from its Scottish owners who founded it in 1768) made Chicago synonymous with knowledge itself. These were not poverty-adjacent enterprises.

A hearty publishing tradition continues. We have longstanding small presses like Third World Press (1967), Chicago Review Press (1973), and Haymarket Books (2001). In 1987, Dominique Raccah started Sourcebooks out of her home with $17,000 from her retirement fund and built it into the largest independent book publisher in the country. Another empire. At the scrappier end, publishers like Eckhartz Press and Long Overdue Books are proving that hybrid publishing models can work right here, right now.

This is not a history of selling out or squeaking by—it’s a history of building, of creating, of thinking big. Examples of thriving abound in our past and present and we should be looking to them for inspiration for future flourishing.

The literary community’s discomfort with money talk is hardly unique to Chicago, but it stings more here because, well, we’re better than that. We’re hustlers. We’re grinders. We brave brutal winters and maximize our summers. We invented the commodity exchange and the skyscraper and deep-dish pizza and house music and improv comedy. None of these came from folks too precious to discuss how something would actually work financially.

Part of it is inherited mythology from far-flung places and lore. The image of the solitary, struggling, indifferent-to-commerce writer is deeply embedded in how literary culture thinks about itself. The artist who never asks about fees is the serious one. The publisher who undercharges really loves books. Caring too visibly about money signals the wrong values.

Part of it is structural. The literary world runs heavily on volunteer labor, underpaid passion work, and the assumption that love of craft will fill the gaps that income doesn’t. The Arts Census numbers confirm the sturdiness of this construction.

Part of it is that somehow we’ve confused talking about, thinking about, wanting—needing— money with being greedy. (Truly, even in our latest era of oligarchs.) They are not the same thing. Asking for fair compensation is not greed. Understanding revenue streams is not selling out. Building a sustainable practice around your writing is not a betrayal of the work.

And part of it, quite bluntly, is that many of those who perpetuate these ideas and circulate all variations of them have the luxury of doing so because they have other solid sources of income, even wealth.

The Chicago Literary Hall of Fame exists to honor our city’s extraordinary literary legacy. That legacy includes writers who struggled economically in ways they shouldn’t have had to, literary organizations that closed before their time, and voices gone quiet because the math didn’t work out in their favor. Honoring that history means being honest about it—and deciding to do something different.

So let’s drop the whispering and the avoiding, and have some radical, electric, broad-shouldered conversations about what’s economically possible. Let’s harness our collective imaginations, creativity, and abundance of skills, personalities, and mettle in service of more intentional economic prosperity and a vibrant, financially sustainable literary and cultural ecosystem—for each other, for creative small businesses, for our fellow residents. Chicago has weathered worse. A literary community that gets serious about our own economics doesn’t just survive the next disruptions, we may help carry the city through them.

This is the first in a series of blog posts I’ll be sharing here, musing and prodding about the economics of literary life in Chicago, about income, pricing, funding models, and what an economically vibrant literary ecosystem in this city could actually look like.

Chicago has the grit, the talent, the history, and, really, the ego to build something that works and shines and amazes and begets copycats. We just have to be willing to talk about the grubby part first.

*as reported by Courtney Kueppers on WBEZ, May 11, 2026.

Sharon Woodhouse founded and ran Lake Claremont Press, publisher of books on Chicago and Chicago history, for 25 years. She now heads the Conspire Creative agency, offering coaching, consulting, project management, and business strategy services to authors and indie publishers. She is the author of the award-winning The Profitable Author: 1,001 Ways to Build a Business You Love Around Your Books, and writes about all aspects of creating holistic, income-generating, sustainable literary businesses on Substack.