on tools for thinking and irritating your readers

In the future, everyone will be world famous for 18 minutes--Andy Warhol (if he'd been referring to TED)

As an editor, I judge the strength of a piece of writing by the weight of its emphasis on a single viewpoint. If you read something written (well) by a person with a substantially different way of seeing the world than your own, it should hurt.

In reading, you take the author’s side long enough to weigh their argument. You’re forced to try the ideas on for size simply to make sense of them. Reading isn’t a dogfight; you have to get in the author’s cockpit whether you like it or not. This can be delightful, if what you’re reading affirms your own beliefs and values. If it doesn’t…


Which can be agony. I edited some books for Penguin’s conservative Sentinel imprint, so I’m all too familiar with this sensation. (If you’re conservative, you just experienced it, too. Sorry, Mom and Dad.)

The degree of pain your writing arouses in someone who disagrees with you is proportional to the pleasure your true audience will feel when they discover your work.

Consciously or not, we sense this power when we write. Fear bubbles up. So we stop writing, or we temper our words until they’re safe and dull and of no use to anyone.

I don’t want to pasteurize my thinking and neither should you, if you’re looking to build an audience. Say something and, when you revise, say it harder.

Recently, I learned that mathematicians around the world are stockpiling Hagoromo Fulltouch Chalk, the so-called Rolls-Royce of blackboard writing implements, because its Japanese manufacturer is going out of business.

(More accurately, mathematicians would probably call it the Cosmos of blackboard writing implements, since Cosmos is their favorite brand of pocket protector.)

Hagoromo boasts an enamel-like finish that protects your fingers from white dust, and writes with a creamy responsiveness that can’t be matched by its competitors. (You’re pathetic, Crayola Nontoxic Anti-Dust Chalk. I can’t even look at you right now.)

In short, if he’d had Hagoromo chalk, Fermat might have squeezed out some more math. And then we’d be calling it Fermat’s Penultimate Theorem.

Tools are important. Sarah Zhang at Gizmodo writes:

“In the 21st century, chalk is still one of the primary tools of mathematicians . . . Powerpoint slides don’t work for writing out a problem step by step. Plus, technology has that annoying tendency of becoming glitchy at the most inconvenient times.”

When creating, you want to reduce friction as much as possible. For mathematicians, that means chalk. For me, that means as much as possible sticking to iA Writer Pro, a rock-solid and aggressively simple text editor. You really can’t go wrong with text.

This philosophy applies to every aspect of your work. The deeper you get into your own expertise, the less complexity you want to tolerate in other areas. (This is why you bring in outside help on your book and author platform, hint hint.)

Plus ça change: Back when I started out as an editorial assistant at Riverhead, there was a particular brand of red pencil preferred by editors and copy-editors. (Does anyone remember what it was called?) When the manufacturer folded, I (ambitiously, considering my dismal prospects at Riverhead) decided to stockpile a few boxes for the day I began editing my own manuscripts.

One red-pencil edit later, I tossed the pencils and switched to Microsoft Word. Still haven’t looked back.

I mean, seriously, a pencil?

books are over (no, not in the way you’re thinking, I’m just hooking you with an overblown subject line)

“Shibumi has to do with great refinement underlying commonplace appearances. It is a statement so correct that it does not have to be bold, so poignant it does not have to be pretty, so true it does not have to be real.”

Shibumi, by Trevanian

(Writers: There’s nothing like a profound quote to kick things off. It’s like, hey reader, this dead person wrote something wise, and I’m repeating it, so therefore I’m equally wise by the transitive law of thought leadership.)

I’ve talked to many both inside and outside the “traditional” publishing industry—know the “traditional” ones by their characteristic briar pipes—about where this whole thing is going. And by “whole thing” I don’t mean books as a generic term, because “book” is no longer a useful generic category. Instead, I mean the kinds of books (and, barf, “content”) I’ve specialized in for years now, the “helping” categories: business, health, self-help. Books that tell you how to do stuff better, whether it’s market your service or channel the astral presence (hint: both involve bullshit).

If you read a lot about books and about the publishing industry in general, you’ll have noticed that in discussing the future of books we conflate these very different categories simply because they’ve been physically similar to each other for almost 600 years.

That’s changed, but our thinking hasn’t. And so we lose sight of the obvious fact that the future of romance novels will be very different from the future of autobiographies, or even science fiction novels. (For example, science fiction novels will simply be called “novels.” By the robots who read them.)

The heads of most “traditional” publishing companies (and their imprints) are trying desperately to keep this artificial conglomeration of content categories together in one big lump—we’re experts at this, they insist, and we have scale—while the demands of each category and sub-category drift further and further apart. It’s no longer sufficient to say your imprint publishes great books. That’s like saying the bartender serves great glasses. The question is, does he know from whiskey?

On his website, productivity expert Shawn Blanc sells Delight is in the Details, a “kit” which offers “practical advice, insight, and inspiration so you can reach for excellence and resist the tide of ‘good enough’ work.” For $39.00, you receive an 88-page ebook, the audio book, 10 audio interviews (with transcripts), 8 Q&A interviews, 3 videos, and a resource index, all with a money-back guarantee.

Look at that site. Clean and compelling, loaded with very good reasons to buy the kit. It scrolls down forever, and it doesn’t waste a word. This is a book cover taken where no dust jacket or Amazon page can go, tailored specifically to this one product.

And look at what he’s selling: an 88-page ebook that hasn’t been padded to 256 pages simply to make the book thick enough to charge $25.95. (No reader has ever complained that a business book wasn’t long enough, by the way.) Plus, an assortment of multimedia materials that aren’t limited by the ebook format or that require special software or a particular device. Shawn isn’t waiting for some slick new publishing platform backed by News Corp. or Time Inc. He isn’t concerned about piracy and using some restrictive DRM that makes it a pain for his readers to read what he’s written. He gives you his expertise in the most convenient and appropriate formats available, and he charges significantly more than we’ve been trained to expect to pay for a much longer “traditional” book.

The selling techniques Shawn uses here are powerful, and could be used by anyone selling their expertise in any form—physical books, websites, audio, video, whatever.  But these techniques have very little relevance to the world of novels or children’s books. And the skill-set and culture and pretty much everything in an organization that would make it good at creating something like this are very different from what you need to successfully publish My Struggle by Karl Ove Knausgaard. And yet most of the top-tier publishing imprints still, you know…what’s the word…work really, really hard to publish these different kinds of content using the same team, the same tools, the distribution chain, the same business model, the same thinking.

No one who actually does what Shawn does thinks that self-publishing is the appropriate road for most authors. An immense degree of skill and experience is still required to compete in the marketplace of ideas. Mostly, experts need publishers, but in the arena of ideas we don’t really have any that can do this properly yet.

I’m arguing for specialization, not by format but by category. Publish business experts, or historians, or mathematicians. Worry about the delivery mechanisms later. What kind of expertise are you trying to share, and with whom? Then build your operation.

There is a huge amount of opportunity for publishers (Big 5 all the way to hybrid) who are willing to specialize their entire vertical operation around a single content category.

OK, if you work in traditional publishing and you feel like I’ve been picking on you this whole time, I pick because I love. Watch this video of a dog dancing the cha-cha:

this post totally has cool book publishing secrets in it

Forget what I said in the post title. I oversold it.

It’s hard to strike the right tone. As the carnival barker, you want to lure the suckers into the tent, but you don’t want them demanding a refund because of the glue holding the bearded lady’s beard to her face, know what I mean?

Of course, you’re not the sucker in this example. You’re the tent.

Ben Leventhal, co-founder of Eater, wrote a Medium article entitled The 9 Habits of Highly Effective Restaurants.

Speaking of which, do we italicize Medium article titles? Use quotes? I’m going to go with vertical bars, a.k.a. pipes.

In |The 9 Habits of Highly Effective Restaurants| Ben identified 9 “indictors” (he meant “indicators”—Ben, I’m available for editorial work 347-394-0222) that a given restaurant will succeed.

For example: “Look at the china. If the restaurant is paying more than a few bucks per plate and the place isn’t jam-packed, they’re assuming you’re ok with a 3x wine mark-up.”

I loved Ben’s list. It’s not about defining every aspect of the perfect restaurant—clearly, success depends on many factors, including luck. It’s about sensible heuristics for quickly identifying winners and losers.

So I’m going to propose a few of my own ways of identifying (or creating) a book project with real potential, whether you’re an author, an agent, an acquiring editor, or a service provider like myself.

The focus here is on books that offer guidance to a general reader. Business, health, self-help, and so on. Other categories can be very different.

Literary fiction, for example, operates in a Bizarro publishing world where authors who smoke unfiltered cigarettes while railing against the Internet and e-books and Amazon and who write everything longhand with a quill and don’t own a phone and who think cameras steal your soul and that the sun is a chariot drawn by fiery horses somehow sell even more copies, particularly if they complain about being poor while living in an apartment with built-in bookshelves in the trendiest neighborhood in Brooklyn.

(Bizarro world is where Bizarro Superman lives. Bizarro is the opposite of Superman, so he says up instead of down, left instead of right, and he’s always raving about his Kobo.)

  1. You want to see a big list, sure, but at the very least you want to see a solid newsletter strategy for capturing lightning when it does strike—when a talk goes viral, for example. Step one is a functioning mechanism for capturing potential book buyers. No, not Twitter.
  2. Forget the stock marketing plan in the proposal. If the author can explain in plain English who will buy copies and why to your face, some thought has actually gone into it. (Thought going into any of it is rare.)
  3. Authors with a distinct personal style fill me with reassurance. Like they always wear a scarf. On the flip side, distinct slovenliness can also be a good sign as 30% of the time that means they’re Internet wealthy and will get to do a Reddit AMA on pub day. (Hint: if they also carry a phone with a shattered screen or use off-brand earbuds, they’re just slovenly. Move along.) Either way, if you see business casual, reach under your desk to activate the trap door underneath the author that leads to the laser sharks. (Note: HarperCollins moved offices and may not have installed the shark tanks yet.)
  4. If you see the author give a talk and come away energized and buoyant and all the white is visible around your irises, you’ve been infected by their stage charisma and can no longer be trusted to decide on the size of an advance. Include someone who didn’t meet the author in the bidding process. (Forget e-books and Amazon. Stage charisma leading is the main reason it’s the Big Five and not the Big Six.)
  5. If you can get a friend excited about the book with a one-sentence summary, and it’s not a publishing friend, it’s that friend from high school, you know the one I mean, it’s not that he isn’t smart per se, but maybe he was more excited about the Entourage movie than he was about seeing Mad Max: Fury Road and you were like, OK, Phil, Entourage was a great show. It was hilarious and no it never got old. That friend. If he thinks the book sounds cool you’re golden.
  6. If the author keeps redefining the book’s audience based on the expression on your face, that’s bad: “It’s for teens with bad spending habits. Teens and adults. Parents of teens. Actually, it’s even better for people with good spending habits. And entrepreneurs. And the C-suite.”
  7. Realistic competitive and comparable titles. If any comparisons are made to Malcolm Gladwell or people with their own TV shows, well, that’s why publishing professionals are issued smoke bombs and grappling hooks.
  8. If the proposal says that the whole manuscript has already been written, stay on your toes. If the author’s online marketing work consists of having purchased every variation of the title as a .com, a .org, and a .net, subtly identify the location of all the exits. And if they say anything along the lines of “11 million Americans coping with psoriasis own ant farms, so if even 10 percent purchase this book, you’ve got a bestseller,” casually tug on your shoes so you roll up completely like a window shade and disappear.
  9. If the author has a company and it’s not clear what the company does and no one you know has ever heard of it but they have awesome offices in Soho or the MPD or maybe DUMBO with snacks and cereal in the kitchen and you’re like, but what does this company do? And they answer you and you still don’t know, you’ve found a winner. Write a 6-figure advance check on the spot out of your personal account.
  10. As an editor, I always looked for a good tan on an agent. Means they’re out there in the world picking up the zeitgeist and not always stuck indoors with their nose in a book. That’s also why you never trust an agent with glasses.

Did I leave anything out?

why books work (tl;dr not sure)

“As for thy thirst after books, away with it with all speed, that thou die not murmuring and complaining, but truly meek and well satisfied, and from thy heart thankful unto the gods.”

—Marcus Aurelius, Meditations

Since I decided to open up my own editorial and marketing consultancy, I’ve talked to dozens upon dozens of authors, editors, publishers, agents, and marketers both in and out of New York.

(If I haven’t talked to you yet, put down that blue mug, fasten your robe, and come to the front door. I’ve been waiting here for 30 minutes.)

I’ve been trying to figure out what the heck is going on in the rapidly changing books-slash-author platform-slash-online education-slash-content-slash-yuck-slash-don’t you hate how everyone says content now?-slash-I think I forgot what I was talking about…

As an editor at publishing houses ranging from the traditional (St. Martin’s Press) to the, well, “other” (Amazon New York), I worked with authors large and small. We’re talking 5′ 4″ to maybe 6′ 4″. Some books worked, most didn’t, and while I usually had my suspicions about why, no one on the team really knew what had happened out there. That’s right: even the copy editors had no clue what drived the success of a bok.

Plus, when we did figure out what had bumped sales, it was often not the reason another publishing professional or author would guess from the outside. Which led me to seriously question my understanding of all the other bestsellers out there.

If a book showed momentum, we’d be all over it, sales and marketing and publicity and managing ed and the secret ninjas and the warehouses all working together to get more copies in stores, field press inquiries, set up interviews, etc. That’s what traditional publishers continue to do best: take books that hit and accelerate their growth into the stratosphere.

But why did these select few books hit in the first place? Often, only the authors (and their often shadowy “teams”) really knew.

Clearly, a select handful of authors had a secret sauce, and they weren’t telling us what it was.

Of course, lots of authors say they have a secret sauce—Penguin’s author questionnaire includes a “do you have a secret sauce?” checkbox—but usually that means “start a Tumblr with pictures of my bookshelf from different angles 3 days before launch and cross my fingers.”

Others were pushing buttons and turning dials on a machine we couldn’t see and making people buy books with it. Lots of books. Even if the books weren’t very good.

(Don’t worry [INSERT FIRST NAME HERE TAG], your book [INSERT BOOK TITLE HERE TAG] was an exception, a great read, one of the best books on [INSERT SUBJECT HERE TAG] I’ve ever read. How’s Judy, by the way? And the kids? Tony still playing JV soccer? Sabrina still the high school laughing-stock on Facebook?)

When I went over to CreativeLive, experts were less shy about revealing their methods, so my position as channel head of business education gave me a deeper look into the mechanics of this secret-sauce marketing.

Together, my experiences as a gatekeeper taught me a lot. But it quickly became clear that if I really wanted to understand why some experts make an impact and others don’t, I would need to get my hands dirty. Wade into the muck. Organize and label my shell collection. (I’ve never understood why that last one is also a popular metaphor for involving yourself in all parts of a job, including the unpleasant ones that call for hard, practical work.)