Failing to Sell My First Book Hurt, But In the Long-Run, It Helped My Writing Life

Sometimes the thing we think we want most is the thing that let’s us see what we really need.

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Between my retail day job, my social life and hustling for freelance writing gigs, it took a full year to write my first nonfiction book proposal. It was sixty-eight pages long. “I appreciate a long, detailed proposal,” an editor at one of my favorite big publishing houses told me on the phone. “This is great.” It was called Crowded: Portrait of Life on a Teeming Planet. No publishers bought it.

Crown, Random House, Ecco, Knopf ─ everyone passed. My agent received the no’s over the course of a few days, but I had her send me most of those emails on one. She offers to keep potentially painful emails from clients and simply pass along the gist, but after giving them time to collect, I requested the messages in order to learn where my book stood and how this process worked. My inbox started pinging right before my lunch break at the tea shop where I worked.

I went outside work and sat on some steps, where I read the rejection emails one after another. Editors’ responses mixed glowing praise of my writing style with clear reasons for declining: too ambitious, too diffuse, too similar to other books in the urbanism category. It needed a different framework; needed to make a clearer case; the subject didn’t need a book-length treatment; hopefully he’ll get a nice offer, though. I didn’t doubt they were right. By trying to cover a lot of ground, I might have spread my book too thin. Maybe I didn’t yet know what I was trying to say about crowding because I would discover that while researching the book. That’s how writing essays worked. It was too late now.

I sat and felt that dark, jittery liquifaction you feel when a person you adore breaks up with you and your guts fill with muck and drain of hope, dissolving your dreams and the very idea that you should dream at all.

“Your talent is obvious to anyone and even those that passed,” said my reassuring agent. “Everyone thinks you’re a talent and we will figure this out!!!” She was triaging my bleeding spirit. I trusted and admired her and was grateful for her patient advocacy. But at that point I’d already figured this out: I quit. No more trying to write books, no more writing hopeful proposals on spec. I decided to get out of writing. Why bother. Fuck the market place. There’s no place for me here or anywhere. I never should have thought I could pull this off.

I sat chewing my nails and stared into space. I could see my mistake. I’d invested too much money and too many years into learning to write narrative nonfiction, and all I had to show for it was grad school debt, a tiny shared apartment and an income stream too small for a person my age. Yes, I loved the essays I’d written so far; they’d helped me make sense of the world and my life. I was proud of myself for staying focused enough to teach myself to write as I’d vowed to do when I was an undergrad, and I was proud of the publications I’d written for. But there’s a point at which you have to accept that you aren’t going to get the elusive thing you’d aimed for, so you need to cut your losses before your losses cut you, and let go of your investment. I’d wanted to publish a book with a big New York press. What did I expect? I knew book publishing was a difficult, risky industry, and I’d learned a skill that was arguably not in great demand. That was my fault. I’d followed my bliss rather than the market. Friends made their living in website design, stock-trading, project management and banking. I chose literature? Was I an idiot? On this devastating day, I felt like one. Retooling your objectives isn’t giving up, I told myself. It’s being strategic. I had tried and failed. It was time to change careers.

I texted my wife Rebekah the news. “I’m sick for you,” she wrote back later that afternoon. “I’ve been sick all day over it.”

As I sat on the steps and brooded, I recognized my other mistake: I’d put too much hope in this one book to get me the money necessary to finally get me out of retail by age forty. That wasn’t publishing’s fault. Once again, it was mine. Book publishing is a business. Your book might be deep and it might be beautiful, but if sales teams don’t think it will sell, commercial presses won’t print it. That should be okay. It’s the deal we writers make when courting commercial ventures. But writers put a lot of hope in our novel manuscripts and nonfiction book proposals. We envision that the advances will free us from our situations, that they’ll top off our bank accounts, let us pay off credit cards, put us in a nicer apartment, maybe make a down payment on a small house, eventually get us a stable teaching job, and, if we’re truly fooling ourselves, even lift us onto some small tier of fame. I relied on that proposal to save me from the service industry. That didn’t happen. With no sale and no advance, I went back to making soy lattes. Literally, minutes after reading the rejections, I was stirring steamed soymilk into matcha. The sense of permanence crushed me. I thought: this is my fate. Food service, not books. Books were too perilous, too unpredictable. Writing was too unprofitable to do this much work on spec for this many no’s. Writing may be a labor of love, but I doubted I had enough love left at my age to keep laboring. Be it book ideas or literary magazine rejections or failed magazine story pitches, the ratio of work to reward was too slim to do forever, and I’d already been doing it for half of my twenties and most of my thirties, relying on low-wage labor and cheap food to finance it. I spiraled into a dark place.

The angry me decided that you can’t sell art to suits in sales departments, that those slick business people never got me in real life, so why would they get me now? I was tired of trying. Not of writing but of hustling, of working retail while writing before work and writing after work and writing on weekends and during thirty-minute lunch breaks, on what felt like every free moment of my goddamn life, and despite a creative era of deep personal satisfaction, and a growing, glowing byline filled with my favorite publications, what did I have to show for all my labor? Not stability or income. Not a savings account or 401K, but chest pains, panic attacks, a crown in my mouth missing for three years and no health insurance for eight years, and increasing debt and caffeine dependence. My despair kept bringing me back to that sense of waste: nothing to show for it, nothing to show. I wanted some money so I could write as a job. That was it. Just write. People did it all the time. I read about their book sales in Publishers Lunch, Poets & Writers and on Twitter. Why couldn’t I? That day, I accepted how unrealistic my dream was.

I share this story not to scare people or steer them away from their literary goals. I share it to equip other like-minds with the power of a fuller picture. So many of us writers dream of writing a book. Part of the MFA experience is built around it: enroll in a program to learn to write and buy the time necessary to produce a book-length manuscript. Even though programs don’t necessarily push this scenario, the vision of many students is to graduate, sell our book-length thesis to a publisher, get a great teaching job and write more books. Maybe some of those books will pay enough to keep our teaching load low. Maybe one of those books will eventually hit really big, even late in life.

We hear about the big deals all the time: a million dollar advance for three books; $250,000 for a debut novelist. We hear about the smaller ones our classmates and colleagues land, exciting successes you’d hoped for them, and the deals that don’t earn huge advances or buzz but that anyone would love to have. We hear less about almost making the sale. It may be tacky to talk about money, but hopefully it’s constructive to talk about how some of us cope with publishing’s crushing close-calls and decide to keep going.

We write the novel, and no one buys it. We write a collection of stories during our MFA, but three years after graduating, it still can’t find a publisher. Neither can our essay collection. The agents you query say publishers don’t want essay collections, they don’t even want memoir as much anymore. The Glass Menagerie 2.0 is no longer a sure-fire-deal. They want idea books, big picture popular science books with cultural underpinnings that tell us why we do the things we do. Those require a proposal. So are our MFA manuscripts dead? Should we table them and write another? We’re at the mercy of the market now, not professors or workshop. We have truly graduated from our MFA. The idea behind your proposal might be stellar, but the market might now support it. Measured in non-financial terms, it’s perfectly interesting, but it just isn’t salable. The news stings. It rearranges your plans, maybe shatters your picture of the future. How to recalibrate?

First thing, writers shouldn’t focus too much on the big book deals and the break-out novels. It’s too easy to get depressed about publishing industry news and let other peoples’ success make you feel like a failure. If you’re writing at all, you’re doing well. Many people with MFAs don’t even get that far. Feel good about it.

Second, instead of book deals, focus on writing the best manuscripts you can, writing the book you want to read, and recognize that the market is a treacherous place. Sometimes what you need to write isn’t the same as what you have to sell. You should keep writing if the writing calls to you, but also know that this is what we’re getting in to. Do it. Don’t let the market deter you, and remember: America has a thriving independent publishing scene. From Catapult Books to Hawthorne Books, Shaffner Press to Civil Coping Mechanisms, Counterpoint to Heliotrope to Outpost19 to Two Dollar Radio, options abound. New York trade publishers aren’t the only ones who might want your manuscript. Read widely, buy small press books, and study the diverse publishing landscape.

I wrote this book proposal in Portland, Oregon a few years after leaving Phoenix again. It was my third formal one. The first proposal covered Canada. Called Canphilia, the idea was to drive nearly 5,000 winding miles on the Trans-Canada Highway, from the Pacific to the Atlantic, and try to find the Canadian identity. Who is Canada? What makes Canadianness Canadian? No modern book of Canadian travel writing had been written by an American. The last work of this kind came out in 1985. I thought I’d found a niche. My agent didn’t sign onto the project. Travel writing was a tough category, she said. Unless it’s France. People want books about France. People didn’t care enough about Canada to convince commercial publishers about this idea. It didn’t matter that Canada was the world’s second largest country by landmass or that it shared the world’s longest border with the US. By then it was clear: writing is a fucked up profession. And yet, I kept at it.

A year after tabling the Canada book, I circulated a proposal about the ESL teacher economy in South Korea. I wanted to provide a vivid, narrative portrait of the expatriate subculture of American teachers working in Seoul, and to simultaneously profile the rising star of South Korea, showing the way cultures rub up against each other and how people learn about each other in these sorts of economic transactions. That year, between 27,000 and 29,000 foreign English teachers lived in South Korea. Some people called this “The Asian Century,” and South Korea, this ancient, sophisticated, fascinating culture, defined it.

Following the Korean War, Korea was one of the world’s poorest countries, a largely rural nation with a mere $64 per capita income. Now it had the world’s fifteenth largest economy, fourth largest in Asia, and the third most populous city in the world. This was before “Gangnam Style” brought worldwide attention to South Korea, so again, from a marketing perspective, I thought I was ahead of the curve. My agent didn’t sign that one either. Too niche, too exotic. People don’t know Korea yet, she said. But wasn’t that how we got there first, I said? I tabled this and buried my debilitating disappointment under the pile of lit mag rejection slips I kept in my cabinet, and powered on. And I kept eating fist-fulls of bulk nuts I stole from the bulk bins at the New Seasons grocery store, chewing as I shopped for canned soup and discounted eggs, and shoving the food in my mouth for dinner. This was where my head was at when I received my rejection emails for my crowded book.

As if to scoff at me, the day I received my rejections, the new issue of Poets & Writers arrived in the mail, offering its usual mixture of encouragement, industry insight, writing tips and dream fodder. “Still, what difference does the name of an imprint make?” said an article about the editor of an imprint. “I’ve never chosen to buy a book solely based on the logo on its spine.” I sat on the couch in our apartment, flipping through the pages. What difference did the logo make? Books by Knopf, Norton and FSG always grabbed my attention. I relied on them. That’s why I wanted them to publish my book. One article profiled three novelists who were excited about “their forthcoming books despite previous publishing setbacks.” In another, an agent offered advice about this, and insight into that, and─who knows. I didn’t even register the specifics, only that I was too angry to see it as anything more than bullshit. I was still in the injured fuck books, fuck art, fuck commerce stage of grief. That was bluster. Once I got my venom out, once my frustration subsided and the hurt passed, I could resume my usual constructive way of thinking and get back to recognizing good advice when I saw it.

Time gave me a sense of scale. I didn’t have to quit writing. Writing was too much an extension of my wiring to quit. I just had to recalibrate my goals. Sure, an advance would be great, but I didn’t start writing to earn a paycheck, I started to examine our inner and outer worlds and offer others a reflection of it. I wrote because stories are how human beings make sense of our world. We should be paid for our efforts, but writing for a living was a dangerous proposition. It’s why certain writers I admired advised you never write just for money. It’s why I would focus on independent presses who appreciated innovative work, and whose books I read constantly.

I got back to work.

Over the next few days, I read and reread all the emails from the editors, thinking carefully about the reasons they declined and what they thought did and did not work about my proposal. Diffuse, ambitious, needs a clearer, sharper framework ─ parsing their sentences, I tried to internalize the lessons they contained so I could put them to use if I ever worked on another proposal, which I was starting to think I would. These were smart, experienced people who genuinely liked books. They’d taken the time to write smart, thoughtful responses to my idea. I should listen to them. My proposal had made it further through the process than most do, and I had penetrated the mythical high level publishing strata that many writers think of as unreachable. My proposal got into boardrooms and acquisitions meetings. People had talked about it. Having phone conversations with book editors was something that I used to dream about. Now it confirmed that I wrote pretty well. I needed to feel good about that, to not just damn myself for failing to sell one book, but to congratulate myself for making it this far. On a more practical level, I now needed to see what these editors’ comments could prepare me for my next proposal. Jotting notes, I reread my agent’s emails. “We will figure something out,” she’d said. Where before I thought there was nothing to figure, my rational side had spoken up and figured out something: this book was dead. I was not. I tossed that Poets & Writers on the table and laid on the couch, listening to music.

A couple editors at different houses really liked the proposal, so we set up times to talk on the phone. After great conversations, both of them declined. They couldn’t get their sales teams on board. I could see why. As I learned from sending my agent a couple of other travel-based book ideas over the years, nonfiction proposals are extremely hard to sell if they don’t have an argument or distinct point of view. People like me might love writing narrative profiles and dispatch-type pieces, but if you think you’re going to publish a whole book of them with a trade press, they had better work together to build an argument bit by bit, combined with some narrative drive. Mine did not. Neither did Crowded.

Eventually, after the last publisher declined the following month, I licked my wounds and got back to doing one of the only things I’ve ever wanted to do in life: write. I resumed work on some new essay ideas. I starting talking with a magazine editor about writing a long profile, and I started vaguely developing a new book proposal about another subject I liked. It was probably not a commercial subject, the way I was approaching it, but I figured it just might not be that kind of book. I would still write it, at least for myself. I also slowly accepted that I would rarely be a commercial writer. I wrote about what interested or perplexed me, and if it sold, it sold. Sometimes commerce and art would intersect. This wasn’t a reason to quit writing. When life knocks you down, you have to get up and brush off. Even if I couldn’t avoid spending the last years of my thirties making tea drinks as a barista, I refused to squander my intellectual assets. I had to make this work.

Two months later, a thriving independent book publisher that I loved emailed me to confirm that they wanted to publish my debut collection of personal essays, a genre which few commercial publishers touch, unless you’re a known entity between novels, or you have something pretty special. I was ecstatic. These were the essays I’d written in the libraries of a university I no longer attended, libraries I ”snuck” into daily, Monday through Friday, while living at my parents’ house, and a few back in Portland. They took years to write.

Here’s how I knew I was still a writer: these events resembled a narrative framework. Rather than looking like coincidences or chance, the progression of the rejections to the magazine’s lessons to landing my personal essay collection, it all resembled a trellis, plot points, chances at revelation. My mind made a story out of them, using the sequence as a timeline, and creating order from chaos. Maybe a shrink would call that a coping mechanism. It certainly soothed. But mainly, it’s how I’m wired, like I’m wired to process this experience publically here.

You didn’t ask me for advice, but if I have much to offer, it’s to believe in your vision of your story or poem, stay open to critique and outsider observations, and write the book you want to read. Everything after that is gravy. Hopefully it’s gravey filled with hundred dollar bills.

Written by

Essayist, Journalist, Burritoist. Longreads Editor. Writing: Harper’s, NYT, Slate, Paris Review, VQR, Oxford American, Kenyon Review. 3 nonfiction books.

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