Writing a NYT Bestseller
All of my clients engage me because they’re serious about writing a good book. They tend to be hungry to learn, and willing to put in the sweat equity to continually improve their writing. That’s what I like. Their high motivation and willingness to work makes ME hungry to work my ass off right alongside them. I want to see them FLY.
Since starting our work together, two of my writers have expressed the hope that their book will hit the New York Times Bestseller list—one on the fiction side, one on the nonfiction side. It’s not an expectation. It’s a BHAG—a big, hairy, audacious goal. It’s an elite target that demands we take our best aim.
But let’s be clear: the New York Times Bestseller list is an incredibly fine pinhole to aim for.
Last week I sat down to paint the reality of this goal in my editorial letter to my nonfiction client. They’re writing a book for a business audience about a process that took their tech company to the top, and they want to share their frameworks to help other people achieve the same incredible outcomes. Here’s what I had to say about their goal of reaching the NYT list. I adjusted it a little to remove identifying material, and added more context in a couple spots for those who aren’t yet familiar with the different paths to publishing.
I hope it’s informative for you, too.
On your BHAG of the NYT bestsellers list
This is an extremely high bar, and the list is actually an editorial artefact more than it is a fair representation of a book’s sales. There’s some interesting material in this post, including a video that goes into some depth about what a shell game it is. Well, “shell game” isn’t quite the right term, but it’s basically a game where the rules don’t really apply because the list curators only pick the titles they agree with on a moral and possibly political level (I’m sure you wouldn’t be excluded on that basis 😂 but just to tell you how the game works).
That said, I’m so game to play this game. I have one other writer who’s also engaged me expressly to aim for that list on the fiction side. He’s willing to put in as much time as it takes.
Here are the steps:
Write a kick-ass book—or at least plan it all out (that’s what you’re doing with the blueprint), and write two sample chapters that’ll flatten the people you want to impress (that’s what we’ll do for the book proposal). Quality counts. This is what you’ve hired me for. I will hold the bar as high as you’ll let me. We should talk about this, because it’s important to actually ascertain your appetite to not just write a good book, but to put up with the iteration, detail and revision required to produce a book that goes way beyond “good” and into the zone of “incredible”. It’s very time-intensive.
Land a kick-ass agent. What’s required to do this is a kick-ass book proposal. There are more steps required in a book proposal than what I suggest above, i.e. it’s a lot more than two good chapters. It’s a crisply annotated table of contents, a compelling synopsis, a bullseye marketing plan (this is where you’ll want to explain how [your PR agency] will support you), plus other key elements that you must NAIL. Landing an agent is a high bar in and of itself nowadays, as agents are absolutely inundated with pitches. And their assurance of making sales is becoming less stable by the day, as emerging market forces push new changes into an old industry in ways that startle everyone on the daily. I’ve even heard of agents who have decided to train as book coaches, because at least over on this side of the fence we can be assured of earning a living in exchange for our expertise and time. We can talk in our next meeting about when to begin the book proposal.
Step three on the NYT bestseller path is to land a traditional publishing deal with a Big Five publisher. That’s Penguin Random House, Hachette, Simon & Schuster, HarperCollins and MacMillan—the New York-based publishing houses. Note that even if you land a prestigious or experienced agent, there’s no guarantee they’ll be able to sell your book to a Big Five publisher. Market forces, the pace of cultural change, and emerging publishing models that are putting pressure on the old guard means the Big Five are increasingly looking for sure bets: celebrity memoirs, books written by celebrities, books by household names like Colleen Hoover, Brené Brown and Stephen King, compelling fiction by promising young authors (because their careers might grow, whereas older fiction authors only have so much runway from which publishers can profit), and books that hit a zeitgeist chord at just the right moment. The Big Five aren’t such big gamblers anymore—there’s just too much to lose. And they’re not interested in books that they know will “do well”. They’re looking for books that will KILL IT.
THEN the work is to create enough momentum in sales to land in the “to consider” pile over at the New York Times. This is where [your PR agency’s] skill set will be of tremendous help to you. There’s some good information in the video [link above] about what’s necessary to produce those high-volume sales in the first week of the book’s release.
I told you a while back that the leadership category is full and thus very competitive, so you’ve got your work cut out for you to land a deal when the category itself is red ocean. That said, you’re [demographic identifier] (a slight advantage in publishing atm), and you built a big tech company (a definite advantage because tech is sexy and because [demographic identifier] are way underrepresented in tech). Also, if you were somehow able to get [super big name in business] to write the foreword, that would shift the game a bit more in your favour. Those are your edges, and those are what you and [your PR agency] are going to play. A lot of Toms and Dicks have great leadership paradigms / programs to help people optimize their teams, and a lot of Dicks and Harrys have programs to help people optimize their lives, so you’re going to need to really distinguish your six-pillars approach to optimizing people’s entire existence. I would also suggest trying to find an even more rare and compelling angle, which our work in the blueprint can surface if you go into it with the willingness to really excavate the truth of this book in your heart. I can’t see that angle yet, but that doesn’t mean it’s not there. Part of what I think I do well is to find that red-hot thread, and then work with my writer to build the shit out of it.
If you do want a Big Five deal, and possibly a spot on the NYT bestseller list, you’re going to need to commit a great many more hours to this book project, and our work together. Have you got that time? Have you got that fire in your belly? Enough to go back over the things I ask you to redo, enough to add more depth when I say it’s lacking even though you have no freaking clue why a given blueprint step means anything at all? Have you got the appetite to revise and revise again in order to make your prose punchier and more vibrant than what you can find in 85% of currently published books?
If you’re a yes, then you picked the right coach, because I am relentless and perfectionistic when someone says they want to go for gold in crafting a great book. It’s taken me three hours so far to write this material at the top of your ed letter, and I’ll read and adjust it three four more times before I’m done.
There are absolutely no guarantees. Us book coaches are so, so clear that the only guarantee we can make in this hilarious Sahara of shifting sands is that we’ll help you write the best book you possibly can—if you’re down to put in the elbow grease.
If you decide at any point that the NYT bestseller list isn’t worth the effort, I can still support you to get a fine book written and, I’m quite confident, sold to a smaller press, with or without an agent, and [your PR agency] will help you reach the sales you’re after in order to catalyze your speaking-and-inspiring phase. You’ll be just as busy and profitable if you go with a smaller publisher [or a hybrid publisher], because the work of actually marketing the book / its associated lines of revenue lies squarely in the writer’s hands.
— Alex
Big essay, right? I could have written more. The ed letter itself was seven pages long.
I’m a nerd for this work. It beats my heart, it breathes my breath, it lights my fire.🔥
I’ve just introduced a new package to my offerings called The Steer—a half-day of solid conversation, no pages, no feedback—that just helps writers grok the publishing game in depth, because few humans actually understand how this complex and temperamental industry works, nor all the steps required in making their dream a reality. I’ve said it a hundred times, and I’ll say it a hundred more: writing and publishing a book is no less complex than starting a business. But it’s a good dream—and it’s an achievable dream.
Come dream with me.