A Clueless Man’s Guide To Publishing

Sam Weinman navigates the long and winding road to that first book deal.

The first time I tried to write a book was shortly after I got married. I was about 70 pages into a novel about twentysomething angst when my wife called from work telling me to turn on the TV. Some plane had crashed into the World Trade Center.

It would be imprecise to say my novel died because of the events of 9/11. For one thing, I might still want to go back to it, provided I scour through all the cringe-worthy passages you write when you’re 26. And for a while immediately after, I tried to keep writing. But as with a lot of people that fall, my equilibrium was off; the loss of friends, the sudden crush of vulnerability—it was enough to halt my momentum, and I never quite got it back. At the end of a week, I noticed I had barely eked out a page. By Christmas, the novel was just taking up space on my hard drive.

Years passed. My journalism career was consuming most of my creative energy, and then we had two boys to sap me of the rest. Worse, I came to accept not writing, like some marathoner who misplaces his running shoes and eventually forgets he ever had them. When my parents would ask me when I’d get back to real writing and not the pithy blog posts I was churning out online, I found myself exasperated by the question. Have you seen my life? I’d ask. Not now, I’d say. Definitely not now.

Then one day, it was now.

In the opening of my first book, which will be published in December, I write about the moment I was given the idea for writing it. It was a tennis match in which my oldest son lost and then threw a small tantrum in the parking lot, which triggered thoughts about losing—how we deal with it, how very often it can shape us in profound, positive ways. The resulting book, Win at Losing: How Our Biggest Setbacks Can Lead To Our Greatest Gains, studies people who’ve endured failure and ultimately benefited from the experience. That this rather ambitious idea arose from an otherwise forgettable kid’s tennis match is true, but what I don’t discuss is the other part—how taking on a book while working a full-time job and balancing a frenetic family life went from this untenable concept to something I absolutely had to do. How exactly that happened is harder to explain. But what I can say is a dormant part of my life had been reawakened, and I was anxious to do something with it.

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* * *

Most writers are this curious mix of insecure and arrogant. I suppose I’m no different. Once I had settled on an idea and started typing away in odd hours, I had produced enough pages where I felt someone needed to see them. My expectations at this point were unclear. A part of me feared the work was a disjointed mess, and the other part was convinced it was good enough to be bound and sold there on the spot (hindsight: it was not). Through a friend, I had arranged a meeting with a respected New York agent who humored my naive questions about how the publishing world worked. As he spoke, I had a stapled pile of papers sitting in a folder on my lap, and I was waiting for a chance to hand it to him. At worst, I would leave the papers for him to peruse at his leisure, but silently I hoped he would start reading on the spot, perhaps politely excuse himself into a back room, and then emerge with a contract for me to sign (like I said, I had no idea how this worked).

This did not happen. But my worst fears never materialized either. A week or so later the agent emailed to say he liked what I wrote, that the idea had promise, but that a lot of work needed to be done. I was happy with this response provided he wasn’t just being polite. Could there be a separate email thread between the agent and our mutual friend in which the agent implored him to stop sending along such losers? I raised this concern to my friend and he assured me no. Agents are too busy to be polite.

In the early stages of my book project, I spent a lot of time Googling, in the same way one might research some new affliction. Why does it burn when I pee? How long can I wait before pestering my agent again? And at what point can I actually call the guy I met that one time “my agent”? I had worked in journalism—first in newspapers and then in magazines—for two decades, yet I realized I knew next to nothing about how books were created. I had a sneaking suspicion part of it involved sitting in front of a computer typing, but that was pretty much it. So I Googled. I researched book proposals and who to send them to, and all of the blogs and forums I frequented featured an assortment of horror stories (“I sent out my proposal and never heard back. I now live alone with my birds.”) I read about money (don’t count on much) and book tours (ditto), and in my bleakest hours, I looked up self-publishing. When people ask how long my book took, I say about two years. But in terms of mental energy expended, it was more like a decade.

But I was at least motivated, and after a couple of months laboring over a book proposal, my agent called to tell me he was ready to send it out to publishers. A writer friend had told me “if you sell the agent, you sell the book,” and if that was the case, I felt I had cleared an essential hurdle. I resisted the urge to ask who he was sending it to and what the conversations would be like. My agent had a lengthy list of clients who were more important than me and was always concise with his responses. Not wanting to push my luck, I mostly just waited.

Incredibly, I heard back almost immediately, which, for reasons that soon became apparent, proved problematic. My agent informed me that an editor who received the proposal was intrigued, and wanted to set up a call. (There was a brief charade of checking my schedule, when, in reality, I probably would have skipped the birth of my child.) On the phone with the editor, a charming guy with an impressive roster of titles, I fielded questions about who I envisioned as the audience for the book, and how long it would take me to write it. I had given no thought to timing and word count, but coming from a newspaper background, I had it in my head that I could turn it around in a couple of months. The editor suggested I probably needed more like a couple of years. Overall, I was encouraged by our conversation, and when I hung up the phone and reported back to my agent, we both anticipated receiving an offer on the book fairly soon.

Here is why I say the swift response proved troublesome because it emboldened me to believe that selling my book would be as easy as unloading an armoire on Craigslist. In fact, it was torture. That first editor ended up passing, and over the next few weeks, I had a handful of similar exchanges with interested editors either by phone or email, and a rough pattern began to emerge: that they liked the idea and they liked my writing, but they couldn’t quite see where my book fits. There was a persistent question about audience, and what I soon learned about publishing is that when you say your book is for everyone, it means it is for no one.

The most demoralizing episode began on a Friday afternoon in May, when my agent forwarded an email from another editor at a major New York publishing house. This editor said she loved my proposal and that her head of marketing did as well, and they just needed to get a few more reads from people around the office before proceeding. There was even a reference to advance money, and the figure jumped off the page—not quite quit-your-day-job money, but enough to make my book feel like more than a weekend hobby. The editor mentioned wanting to set up a call for that afternoon, and though I was scheduled to play golf, I told my agent I could make myself available. Don’t worry, he said. We can catch up Monday.

Over 18 holes and into the weekend, my mind raced ahead to selling my book and all the spoils that go with it. I thought of telling my parents, and of my author photo, and of a book signing, in which a line of fans snaked out the door and I charmed them in a newly-purchased sport coat. I succumbed to thoughts of what I’d do with a sudden injection of cash from my advance. On Monday morning, still beaming, I emailed my agent to tell him I could do the call whenever, and he responded minutes later.

It’s not necessary, he said. They’ve decided to pass.

The words were crushing. I remember needing to close the doors to my office, and blood rushing into my cheeks. I forwarded the email to my wife with a one-word qualifier: “Devastated.” Even then the irony was not lost that I was pitching a book about how we deal with losing, yet my response to losing out on a book deal was to want to throw a chair through a window. There was no upside. I didn’t care about how it might shape me over time. I only knew that it hurt, and I was pretty sure I was going to vomit.

Whether rational or not, I came to see the repeated rejection of my book idea as a rejection of me as a person, and of the way I see the world. In retrospect, I’m not sure it was that as much as simple economics. As much as we like to think publishing weighs each book solely on its literary merits, it’s not unlike most industries where there’s an underlying aversion to risk. I was an unproven author with an idea that straddled too many genres, and there was no guarantee my 40-page proposal could translate to a full-scale book. From a publishers’ perspective, there wasn’t enough to ensure a return on an investment.

Whatever the reason, my primary objective had evolved to where it was no longer to sell my book, but to relieve myself of the misery of not selling it—as if an equally palatable resolution would be to forget I ever had the idea. This was impossible, of course, and to complicate matters, my agent informed me that he had the book out to a few more publishers and the whole thing might take a few months. His advice to me was to relax and sit tight.

He apparently didn’t know me very well.

* * *

By now I’ve spoiled the ending of this story. I already told you I landed a publisher for my book. Even worse is I’m unable to provide much insight into how. The whole thing remains so arbitrary. Even within such cautious parameters, sometimes it does come down to a gut instinct, and the right collection of words resonating with the right collection of people. In hindsight, I can see how alarmingly close my book idea flirted with oblivion, or at least to an assortment of difficult questions: whether to write it on spec or to try to publish it myself. I should make clear that these are both noble pursuits, and many people of stronger character than I have seen through their artistic vision without assurances of compensation. I just wasn’t sure I could be one of them. I had a full-time job, and two kids and a mortgage, and if I was going to sequester myself off from my family on weekend afternoons, I preferred knowing something tangible could come from it.

Remarkably, something did. In whatever frustrating moments that have arisen in writing, revising, and now trying to market my book, I try to think back to those precarious moments that led to my book deal: the initial encouraging email I received while standing in line at Whole Foods, the inevitable word-parsing after my introductory phone call with the interested editor, the final word from my agent announcing we had a good offer and we should take it. I hope to land more book deals in the coming years, but it’s hard to imagine one feeling more consequential than my first.

So why did my book sell? This is another one of those questions I would have Googled, and my lame answer is that I don’t know. I have never put the question to my editor, for the same reason I’ve never asked my wife why she decided to kiss me that first time all those years ago. To ask the question is to suggest it could have been a mistake.

If I had to guess, though, I’ll first do away with some false modesty. I think the premise of the book is important, and while I’m hardly the first person to suggest that losing has character-building potential (or to do so in book form) I feel I approach the topic in a fresh and relatable way. I also go back to that curious mix of arrogant and insecure, how I was shameless enough to put myself out there for judgment, but still desperate to make it work. I had convictions about my book, to the point that I would have stopped short of turning it into, say, a graphic novel about superhero cats. But as someone who had no leverage in these conversations, I was always careful to listen to the people who did. It’s worth noting that the finished product—which hits bookstores today—has only faint resemblance to the stapled pile of pages that I brought to my initial meeting with my agent. I suppose I could lament straying from my initial vision, but not when I realize now my initial vision wasn’t quite right.

Meanwhile, if I were to impart advice to other aspiring writers, I might as well steal some material from my book, much of it fueled by people with richer life experience that my own. I’d tell you to manage your expectations. You’re free to envision your book as a bestseller, but you’re better served establishing more modest goals first. Write 500 words before breakfast. Tighten everything before bed. Solicit feedback from people you trust. The most unsettling part of book publishing is in all the things you can’t control. For your sanity, I recommend immersing yourself in the things you can. Another concept I explore in my book is the importance of process goals over results goals. In the context of writing a book, it would mean to focus on formulating a meaningful sentence or conducting a worthwhile interview, and not fixating on where the book ranks on Amazon.

As I write this, I have no idea if my book will be a monstrous success or disappear into the ether after a couple of weeks. This is not the part where I tell you how I’ll be OK with either outcome. But I do take some solace knowing the process itself will hold up as the most important reward. The goal in writing any book is to connect with a meaningful segment of readers. What I didn’t anticipate is how it helped me reconnect with myself.

Featured image: Everett Collection/Shutterstock.com
Author Photo: © Charlie Weinman

SAM WEINMAN is the digital editor of Golf Digest. Prior to that, he was a senior writer for The Journal News in Westchester County, New York, where he was honored with multiple national writing awards for his coverage of the PGA Tour and the National Hockey League. His work has also appeared in USA Today, Golf World, Yahoo! Sports, ESPN the Magazine, and Sports Illustrated. A graduate of the University of New Hampshire, he lives with his wife and two sons in Rye, New York, where he coaches multiple youth sports teams. Win at Losing: How Our Biggest Setbacks Can Lead To Our Greatest Gains is his first book.


SAM WEINMAN is the digital editor of Golf Digest. Prior to that, he was a senior writer for The Journal News in Westchester County, New York, where he was honored with multiple national writing awards for his coverage of the PGA Tour and the National Hockey League. His work has also appeared in USA Today, Golf World, Yahoo! Sports, ESPN the Magazine, and Sports Illustrated. A graduate of the University of New Hampshire, he lives with his wife and two sons in Rye, New York, where he coaches multiple youth sports teams. Win at Losing: How Our Biggest Setbacks Can Lead To Our Greatest Gains is his first book.

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