Can you plan to write a classic?

Two books to show you how. Plus, David Mamet's big sales vibes

Hey there. This is Poe Can Save Your Life, a newsletter about the modern-day arts and the olden-day arts, and this post is the second in my new series about how to sell books to readers—or simply sell more of whatever you’re selling.

Eventually, we’re going to get to launches, Bookbub promotions, Amazon ads, hand-selling at festivals in meatworld, etc. But before we do that, I think we ought to talk about the product-development stage, asking ourselves some very big, sexy sales questions.

Can you set out to write a bestseller? What about a literary classic?

The playwright David Mamet spent of a chunk of his 20s working as an over-the-phone carpet salesman.

He hated the job. It was just as demoralizing as it sounds—paging through the phonebook to hock flooring when what he really wanted was to be a writer.

One night, Mamet was blowing off steam at a Chinese restaurant near his office, and he overheard some guys talking a mile a minute in the booth behind. It turned out they worked in an even shadier business than he did. They were selling real estate over the phone, using tactics that sounded borderline criminal.

As Mamet said later, “It was 6 to 5 and pick 'em, whether it was actually a crime or not. But these guys were all genius salesmen, stroke crooks, stroke confidence men.”

Fascinated, he kept eavesdropping. And eventually, in his 30s, Mamet used the material to write Glengarry Glen Ross, a play about shady real-estate salesmen. Stroke crooks. Stroke confidence men.

Glengarry Glen Ross opened in London in 1983 and, after a brief, bumpy start, grew to be a smash hit. It was nominated for a Tony and, in 1984, it won the Pulitzer Prize.

Mamet sold the film rights for $500,000. He earned another $500,000 writing the screenplay. Adjusted for inflation, that’s a $2.7 million payday.

But what grabs me is not the cash. It’s the extremely literal example. Mamet started with shady sales tactics—and embraced them, at least in a sense. Then he wrote the equivalent of a bestseller. A modern-day classic.

I actually had a similar job myself, not long after college, though with far less spectacular results.

I wasn’t selling carpet over the phone. Instead, I ghost-wrote motivational “content” for salespeople.

Each weekday I’d draft emails containing a single inspirational quote, plus a brief explanation in case the quote proved too hard to understand. These emails then shot out to hundreds of thousands of people—my boss’s giant email list.

One day, wondering who all those people might be, I scanned the email database. A lot of them seemed to be your local State Farm rep, or selling furniture at Macy’s. Others sold airplane parts or hugely expensive medical equipment.

Sadly, I am not David Mamet, so my reaction was—I’m ashamed to say—closer to contempt than fascination. What a bunch of sad sacks, I thought, wasting their lives on used car-lots and behind Clinique counters! No wonder they need to be exhorted every day to:

“Never give in. Never give in. Never, never, never, never.”

—Winston Churchill

Or:

“Always be closing.”

—David Mamet

I mean, who needs supposed wisdom like that?

More fool me. I couldn’t see that I was in that audience—one more struggling salesperson. Instead, I felt superior to them, holding them at arm’s length because of course I had NOTHING in common with a bunch of tacky salespeople. I was only working that dumb job so I could write novels by night, and as soon as I sold my first one for big bucks, I’d leave them all in the dust!

Feel free to laugh. I’d laugh myself, but the wasted time stings.

Protected by that helmet-like ego, I managed to learn basically nothing for another couple years. I never wrote a modern classic. I never managed to sell a novel, full stop, and you know what? I don’t think that’s a coincidence.

We do ourselves no favors by ignoring sales, sales tactics, and sales people. It’s unproductive, impractical, unkind. Besides, YOU AND I ARE IN THE SALES BUSINESS TOO, and the sooner we realize that, the better off we may be. So let me share the two best books I’ve ever read on the topic of selling books. Both are life-changing-ly smart, both about the nexus of craft and business.

In Perennial Seller: The Art of Making and Marketing Work that Lasts, Ryan Holiday opens by describing the market that we are all competing in, which is hmmm let’s call it daunting:

More than four hundred hours of content is uploaded to YouTube every minute. Every year, more than 6,000 startups apply to Y Combinator. Ten thousand people get advanced degrees in drama. More than 125,000 people graduate with MBAs each year, and more than 300,000 books are published in the United States. Even with only five percent unemployment in the United States, some eight million people are looking for work.

Holiday’s book is—like it sounds—a guide to creating books that people want to buy. Even more specifically, it’s a guide to creating “strong backlist titles,” which is the publishing term for books that keep selling year after year after year.

Holiday argues that you can and should aim to “backlist well.” Stop sweating the splashy launch, instead concentrate on the long term, because what’s the point of putting so much time and angst into a massive project if it’s dead by year two? Aim to be evergreen, and you’ll earn the maximum return on your investment.

You don’t have to write a classic to be a backlist success, Holiday says. All you need to do is create work that can survive for the next 10 years—because, owing to what’s known as “the Lindy Effect,” books that survive for 10 years tend to survive for another 10 years, and then for another 10 years, forever.

This is a much, much easier goal to achieve, no matter your creative discipline.

Plus, he’s got marketing ideas. Great book. Highly recommend.

Rob Fitzpatrick’s Write Useful Books: A Modern Approach to Designing and Refining Recommendable Nonfiction is just as smart. And because it is technically a guide for people looking to creative passive income streams through self-publishing on Amazon—rather than for artists making art—it is full of delicious, invigorating heresies.

The money quote:

“Instead of trying to figure out how to market whatever book you happened to write, a book can be intentionally designed and refined toward maximizing word of mouth and back-catalogue potential,” Fitzpatrick says.

Thinking of sales from the very beginning? Yes, and it would be hard to overstate how much practical instruction he offers about how to do that. In Fitzpatrick’s view, sales thinking is inseparable from craft concerns, and in the last chapter, he boils it all down to a highly specific work/craft/sales plan.

Here’s what he suggests, reduced to a balsamic glaze:

• To start, define the audience you’re writing for and what their needs are. Don’t shut the door to your studio. Keep this audience always in mind.

• Test your project with readers long before it’s finished. Don’t wait to feel ready, go ahead and seek feedback. Then address any negative feedback, iterate and improve. Aim to keep readers reading.

• Understand that engagement and recommend-ability—both of which are key to sales—“rely on readers rapidly extracting significant value from the text.”

• In conclusion, focus on the reader experience above all, that is, the “pacing of value received over time spent.” Always look to boost the value per page.

Can his plan work? Well, here I am quoting his book, which I’ve read twice, and recommending it to you.

Maybe we won’t produce classics, per se. Maybe we can’t, because that’s a matter of Mamet-level talent. But Mamet’s example shows us that, crucially, sales concerns aren’t incompatible with high art. And while many people worry more about the market corrupting their work than they do about producing marketable work, my strong hunch is that most of us are in no danger of completely selling out, anyway. None of us get into this for the money, or—God knows—stay in it for the money. So eavesdropping on the sales guys at the next booth over isn’t exactly going to do us any irreparable harm. It’ll probably do us good. As for me, I only wish I’d seen all this sooner.

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A Good Link

Here are links to Perennial Seller and Write Useful Books. To be clear, I don’t earn anything recommending them to you. It’s just that they’re both so good I can’t shut up. My own book is somehow still on sale for $2.99.

As always, thank you for reading. Wishing you the best as you unfasten your ego helmet and replace it with a sales mindset um wow this analogy is going right off the rails, never mind, you know what I mean,

Cat