Anatomy of A Failed Book Proposal

The deed to my deep holdings in the fabled Hollow

I’ve been copyediting the forthcoming Guide to Literary Agents 2012 book, and seeing all of the do’s and don’ts on sending your queries and proposals to agents reminded me that one of my big ideas for a book flamed out a little while back.

Since I was familiar with the fundamentals of writing a book proposal, I think I put together a reasonable effort, one that addressed the usual requisites of Synopsis, Chapter Outline, Sample Chapters, Market Overview, Platform, and Blithering On About My Background. If you Google “How to Write a Book Proposal” you’ll get results out of the yin-yang (wipe them carefully), but Michael Larsen’s How to Write a Book Proposal (updated to its 4th edition) is considered a classic.

If you can no longer bear the act of reading words on a page (the horror!), you can listen to Ted Weinstein’s Book Proposal Bootcamp audio recording, which is quite good. He has other proposal-writing tips on his site as well.

It All Starts with a Drink. No, I Mean an Idea!
Of course, you need an idea for the book. Mine started with a callow, whiskey-drinking youth who, upon seeing a prompt on a Jack Daniel’s bottle urging fans to write the distillery, wrote something like this: “Why, not only do I enjoy consuming Jack’s finest in a conventional way, but I also brush my teeth with it, and keep a glass on my bedside table, at the ready to ward off night sweats and other less congenial spirits.”

Little did I know that would prompt a tide of strange letters and documents, and even stranger objects (a rabbit’s foot, rubbing stone, chewing tobacco, sippin’ glasses and more) sent from the distillery to me. My first return letter from them came 35 years ago. I received another a month ago and I’ve faithfully returned the favor back to them, quirky letter for quirky letter. Even when months would go by without receiving a letter, that’s a lot of correspondence, marketing gimmick or not. (A lot of whiskey too.)

Thus, my thought that were I to package up the correspondence, and scans and photos of the mailed oddments between us (sent through their sister organization, the Tennessee Squires), and include a kind running chronology/commentary of what was happening personally and socially over the course of the correspondence, that would make for a weird, whiskey-soaked memoir. Egads, a book!

Putting the Kibosh on the Korrespondence
Anyway, if you scan the proposal, you can see that it’s a fair amount of work to put one together. It was composed a while ago, so some of the info is out of date. But one issue that Little Tommy forgot (and which was pointed out only toward the end of sending it out to a number of agents): I don’t own the copyright to letters sent to me. And when I politely inquired of the Tennessee Squires (of which I am a bonafide landed-gentry member) if I could assemble all our correspondence in a book, they politely turned me down. I asked twice, but no go. They just weren’t interested in publicity about the Tennessee Squire organization. Or they didn’t like the smell of my breath, who knows?

Anyway, I still might publish a shorter recounting of all this high-proof business, because it’s amusing. The next proposal I write, about Hugh Hefner’s pajama collection, will have all copyright issues solved in advance.

Chopping the Copywriting and Creative Writing Salad

Copywriters that have a clearly defined niche—”I write sales letters for mid-tier businesses selling nuclear-powered rabbits”—are both constrained by their choices and freed by them. They are constrained in that they may have always dreamed of writing sales letters for nuclear-powered goat companies, but instead they are known as the rabbit guy, and thus they don’t want to dilute their focused offering, and potentially blur the boundaries of their defined space.

However, they are freed from casting their “I-need-new-work” lines in the thistle-tangled fields of businesses small, medium and large, who might peddle soap made from recycled comic books, or tongue scrapers for denture wearers. Generalist copywriters tend to a casual work garden of mingled (and sometimes flopping) stalks, colors and scents, while the specialist might have a sturdy monocrop of clients and cutoff dates.

You might guess that I’m a generalist.

The 360-degree Rotating Exorcist Head
I’ve thought about trying to restrain my 360-degree rotating Exorcist head (minus green spewings) of writing endeavors, but it’s just not my nature. While I can admire the ferocity of focus some copywriters employ, I can’t join their ranks—I don’t think I could breathe. And, genial bigot that I am, I have to sing the praises of the generalist’s keys, because polymath writing pursuits are inherently interesting for their variety. This month alone, to wit:

  • I finished an article for Fine Books and Collections magazine on the makers of exquisite and zany handmade books, touring the U.S. in their gypsy wagon.
  • Finished editing a book on social media for nonprofits.
  • Edited the first in a series of short books on Nonverbal Communication in Dentistry.
  • Wrote logo taglines suggestions for a home design and remodel company, and begin writing their brochure copy.
  • Discussed writing “replies” for a company that’s developed an advanced virtual personal assistant chatbox app; the replies will cover the branching potentials for suggested questions that users might want answered.
  • In discussion with a company that needs someone to update the documentation for the new version of its novel-writing software.
  • Am writing my two monthly articles (a recurring gig) for the Airstreamer, Airstream’s email newsletter.
  • Sending out queries for a variety of articles, many of them travel-related (though a few are about whiskey and one about old cars).
  • Sending out short older short stories of mine to some lit magazines.
  • Berating myself for pausing in what had been a steady (and productive!) half-hour of writing per day on my novel, having used Thanksgiving and then Christmas and then my father’s death for an excuse for not doing the work. Get after it, man!

Building Expertise, by the Paragraph and by the Project
Now, I have varying degrees of expertise in the areas above, but having written and edited nonfiction books, having written question-and-response dialog for software products, having written a novel (unpublished), having written travel pieces, having written brochures, heck, having written lots of grocery lists, I’m confident I can deliver what each organization needs, granting the many iterations of review and rewrite that some projects necessitate. For many writers like me, once you write website copy for a company, they may call you later to write headlines for an ad.

You might not have written headlines for ads before, but the good generalist will always pipe up with a merry “Yes!” when asked about their ability to write a heady headline. Many fundamental writing skills translate across boundaries—cross-writing is often more comfortable than cross-dressing. (High-heeled pumps just don’t work well with my size 13s.) So, if you are breaking in to the copywriter’s fold, and you’re thinking that you could write sales letters not only for the nuked goats and rabbits, but perhaps for radium-isotope gerbils too—go for it. Next thing you know, you’re a reptiles-with-battery packs specialist too.

How to Make Your Writing Word Wishes Come True

This is an IDEA (though it resembles a butterfly)

I’m a guy whose wishes are words. And whose wishes are FOR words. By the clock, the wished-for words are straight-spined and modest, assembling in tight, orderly rows. But when work gives way to whimsy, that’s when words can stretch, flop, and peep around corners to see who’s looking.

The division is due to the fact that I’m both a business writer and a fiction writer, and not only do the twain not meet, but the twains don’t even arrive at the same station. And that pun is not nearly as painful as trying to reconcile the two worlds of words.

Sometimes, there is a truce of sorts: a brochure on streaming video might have a little stream of consciousness, or a character sketch might call for a pencil tipped with the driest of logic. But most of the time, when I have to travel between the word-worlds, it’s a difficult, deliberate journey—an enterprise that requires even more than Thoreau’s dreaded change of clothes.

However, I want to avoid the sense that being a painter or writer or sculptor confers any elite status or implies some exalted perspective. I’ve been a staff copywriter, freelance essayist and fiction writer for years, and it’s often more a matter of managing deadlines than swooning in inspiration. Keeping the queries fresh. Being thick-skinned about the seemingly inevitable “no” that you get from most publishers. I’ve learned to just shrug and go to the next query or project.

Words for the Plucking
However, there are some moments in the writing process, where words seem to be bright objects that can be plucked out of the air and strung together in serried ranks of complement and charm. Out of nothing, a paragraph that prances—or one that cries and bleeds. In those moments, it’s less the affected pose of practiced art, but rather a kind of verbal husbandry, a farmer grateful for an unexpected crop.

This isn’t precious wordsmanship, it’s grace—and I’m grateful when it occurs.

What I’m getting at, is that at some times in the creative process, it’s less a “me” than a “Wow!” (Conversely, it’s more often, “That’s shit!”—but that’s realistic, not wallowing.)

But perspective is king: there can be beauty in the way a bus driver weaves her route, how a seventh-grader whistles a made-up tune, where the making of a good sandwich is an artful act. Those moments of grace can be fleeting, but a good sandwich is forever. Well, until lunch.

Consider this:

“It is necessary to write, if the days are not to slip emptily by. 
How else, indeed, to clap the net over the butterfly of the
moment? For the moment passes, it is forgotten; the mood is gone;
life itself is gone. That is where the writer scores over his
fellows: he catches the changes of his mind on the hop.”
— Vita Sackville-West

Keep hopping, and snap a net on that nervous mind.

Magazine Editors (Gasp!) Are Actually Human Beings

I know, I know, all of those editors who have rejected your queries or articles are obvious emissaries of Baal, troglodytes, fresh steaming cat poop or much worse. Over the submission years, I have declared them among the seven princes of Hell (or at least in the league of incompetent cable installers). But I recant my earlier denunciations, and with good reason.

For all of the queries flatly unanswered, or for those receiving the peremptory “We can’t use this,” there are editors who take the calculated moment from the lunacy of today’s publishing world and offer a statement of encouragement to the anxious author. Or better yet, a response that leads said author to explore another editorial opportunity with the publication, if the initial submission doesn’t cut it.

Here’s an example, using two magazine editors who both exhibit those alarming traits of decency. I’ve written for Airstream Life magazine for years. The editor, Rich Luhr, originally solicited me to write for his then-new magazine after he’d seen a piece of mine on Airstreams on the Net. Now, having an editor ask you for a piece out of the blue is gift enough, but over time Rich has grown to know my work, and often assigns a piece that’s tuned to my sensibilities. Props to the man.

Recently, he was working on a new specialty magazine for Mercedes owners. I put in some time on a few articles, but Rich couldn’t find the advertising base to support the publication. He had the grace to offer me a kill fee above the price I’d requested, because he knew I’d done a lot of research time. Above and beyond.

Do the Article Two-Step
That ties in well with an editor I just started corresponding with. She runs a Mercedes magazine in the UK, and I sent her one of the articles written for the lost US mag. We went back and forth a bit, and finally she decided that it wasn’t right for her. But I mentioned VERY casually at the end of my “thanks for listening” that I could write a piece about my chariot, an aged-but-stalwart 1981 SL 380.

Bingo! I have an assignment that I initially hadn’t conceived of, just because an editor took the time to explore the potential of other article ideas—or because they simply opened a conversation. There are a few lessons here, but the main ones are that once you are actually having a conversation with an editor, be conversant: recognize that they are open to you as a writer, even if they’re not immediately buying what you’re writing.

And once the conversational door is open, you can walk in so much more freely than if you are sending out your first (and oftentimes) stiff query. I recently had a series of email exchanges with the editor of an in-flight magazine. She didn’t go for my initial query, but took the time (in just a few sentences) to go over what the magazine was looking for. I sent her another query, which was discussed, and which prompted another. Now, none of these ideas actually worked for the magazine, but I know from the quality of our exchanges that I can approach this editor on a comfortable, conversant basis in the future.

Second Dates
And if you’ve published even one piece for a magazine, think to approach those editors again, if you have a quality idea. I have written pieces for a couple of editors who publish wine-and-spirits world magazines, and now I don’t have to write a formal query with my publishing credits and other tedium; I can start right in with “Hi Tim. I had an idea for a piece…”

Obviously, you don’t want to badger editors with lame queries so that they wonder why they ever published you in the first place, but once you have an editor’s ear, you’re miles ahead of the game. (If you try to get their other ear, though, they might press charges.)

Query Don’ts and Query Dos

Before I give some props and malaprops to good and bad query letters, I want to put in a good word (“pizazz,” perhaps?) for the Write-Brained Network writer’s group, which is looking to nudge its network of engaged writers over the 100 mark—and you could be the one to clap that ringing bell. Write Brained (led by the effervescent Ricki Schultz) is a fairly new group of writers from all over the country (and indeed some from out of the country) who critique each other’s work, supply contests and prompts to gin up your monthly word counts, post new approaches and developments in the world of writing, and much more. Check it out.

So, query letters. Below is a bit of bilge I penned that shows you how to oppress and alienate a literary agent with your fiction project. (Note: if you steal my sterling idea about the novel, I demand the foreign-film rights.) Below that is an actual query for an article of mine that was published in Writer’s Digest a few years back. Note that the first few lines of my query lead are the published article’s lead as well: write the query lead as though it could be the article lead—it displays your writing chops, organizes your thinking about the rest of the article, and it will save you time as well.

The So Bad, It’s Good (and Ugly)
Dear Agent (If you aren’t the right agent for my pitch, please forward this to the right agent. And please let me know you’ve forwarded it, and to who. I mean “whom.” Whomever it was forwarded to, that is. Whatever.):

So, I’m pretty sure I’ve invented a new, popular genre for my 263,437-word novel, The Nightmare from Which I Never Woke: I call it “high-fi, transmedia sci-fi.” It’s high-fi because I wrote the whole thing during a series of peyote-induced trances. In the desert. So, it’s like pure and all.

It’s transmedia because it will have some clickable pages that will send the reader to websites where they can order t-shirts. It’s sci-fi because the world I created has two suns. (I can work with editors if they need it to be three.)

Anywho, there’s some saga-like multigenerational stuff on my main planet, Hortog, and wars with lots of futuristic weapons (with step-by-step details on their manufacture and operations). But it’s really a love story, because my main character, Glig, has sex with an alien, who’s kind of like an old-fashioned egg-beater.

The novel’s also very meta. You know, self-referential and informing.

My mother has been hounding me to send this query, because I haven’t had much income for a bit, so if you could send me a little chunk of the advance now, that might help get her off my back. By the way, I paid for one of those deep Internet searches to find out your home address, so if you’d like to discuss this in person, I’m there in a heartbeat. I know you are busy—I will bring the coffee!

By the way, if you aren’t interested in this book, I also write a kind of YA-haiku combination that is killer.

PS I think my novel could be a series.

This query stinks up the joint because it addresses a generic agent (agents love the names their mothers gave them), it ruminates on pointless issues, it’s specific when it should be general, it’s general when it should be specific, and in offering to stalk the editor at a coffee klatch, it veers into prosecutable grounds. Though that YA-haiku thing might work, if it had a banging DJ.

The Good (Even My Mother Thinks So)
Dear Maria Schneider:

First-person essays span space, time and subject: the city dump, an obsessive bird, or a toy from the 60s—all subjects of essays I’ve published—are just one shuffle of an endless deck of compelling themes. It’s never the subject of an essay that tells, but the style and stance of its author. What might seem the least likely of essay subjects can be made a piquant page-turner by a writer’s winning hand.

I propose an article for Writer’s Digest on Crafting the Personal Essay. The article would cover these sections:

• How to choose a subject that suits your style (and vice versa)
• Finding subjects in everyday life
• Fleshing out topics (whether they are existing personal interests or burgeoning ones)

• Distinction between slant and topic
• How to choose, apply and maintain essay tone
• How to blend personal perspective with facts

• The presence of the author (formal/informal, in the background or up front)
• Avoiding heavy-handedness while promoting point of view
• Authority with a light touch

The Lead
• How to hook the reader
• Building on the lead
• The use of declarative sentences, humor, restraint and exaggeration
• Divergence from the lead

• Structure and cadence
• The musicality of words
• How to sneak up on a reader, and how to overwhelm them
• Maintaining momentum and topic drive
• Layering of ideas

• Packing a punch at the end
• Circling back from your lead
• Customer (reader) satisfaction

• Pitching your story

For relevant article sections, I’ll provide short examples of good and bad expressions of the outlined technique or approach. I will also cite some examples of essay compendiums that are strong representations of first-person essay writing, such as Philip Lopate’s The Art of the Personal Essay.

I’ve published essays or stories in the San Francisco Chronicle, Traveler’s Tales, the San Jose Mercury News (West and SV magazines), Things magazine, Verbatim magazine, and others. My website, has a number of my published pieces under the Freelance and Fiction links.

Please reply or give me a call if you’re interested in seeing my manuscript or in discussing the query further.

I look forward to hearing from you.

Tom Bentley

This query is directed to a specific (and relevant) editor, it opens with a strong lead, it clearly and explicitly discusses the article scope, it has some writer’s bio info, and it invites the editor to discuss the article possibilities. The editor is given a good sense of what the writer could do with the potentials outlined in the query.

And b’God, they even paid decently for it…