Staying Loose Versus Staying on Schedule—Pause Before You Set a Due Date

Clock fleur de lisAt what moment do you schedule the due date for a book manuscript? When do you dare make the commitment to deliver?

I’ve answered these questions many times during my years as a freelance book editor. Clients require a due date. Publishers want to know when they can expect a manuscript. Of course. They have a right to make those requests. And I comply.

However, the truth is that I am often just guessing. Or telling people what they want to hear. Or both. And when my due date is unrealistic, I pay the price by working evenings and weekends and pulling the occasional all-nighter.

When will your book be done? I only wish I knew.

What I often want to tell people—and don’t—is that their deadlines are meaningless. People frequently set these dates without considering whether they’ll actually make time to write, whether they’ve done enough research, or whether they have anything to say in the first place.

For years I’ve seen my fear of setting due dates as a personal failing. But recently I’m reading about smart people with experiences that back me up. For example:

  • Leo Babauta, creator of Zen Habits wrote 50,000 words for his new book, scrapped them all on the basis of feedback from reviewers, and started over. I admire that. It’s gutsy. But can I produce 50,000 words for a client and then announce my intention to scrap them all? I hesitate to consider the consequences.
  • Denise Shekerjian wrote Uncommon Genius: How Great Ideas Are Born, a book of conversations with 40 winners of the MacArthur Foundation’s “genius grants.” Many of these creative people testify to the importance of “staying loose”—allowing for time to experiment, flounder, fail, and wait for connections between ideas to appear on their own. But can I tell clients who have a production schedule that I need to “stay loose” for a while with their book project? I can just see the look on their faces.

So, when do you commit to finish your manuscript? And how do you set a date that spares you from suffering?

I’m no longer sure how to answer these questions. I’ve got hints, such as writing a book proposal first and allowing more time for the first edition of a book than subsequent revisions. But I feel largely in the dark.

If you’ve got answers, I welcome them.       

Never Face a Blank Page—Easing the Transition from Research to Writing

PICT0846One of my goals for the short time I have left in this body is to persuade you to avoid ghostwriters. (See this and this). My motto: Write your own stuff. With this goal in mind, I offer ways to reduce or eliminate pain points in the writing process.

One of these pain points is the transition from doing research to actually getting some writing done. You can ease this transition by seeing writing as an act of transformation rather than creation.

More specifically, you can approach research and writing as a process of:

  • Collecting sources (what’s already been written and said about your chosen topic)
  • Extracting juicy quotes from those sources
  • Revising those quotes

The beauty of this process is that at no point do you face a blank page or screen. The act of “writing” is simply taking the quotes you’ve already collected, rearranging them, rewording them, and adding your own ideas.

There are successful writers who use this method. Consider two: Steven Berlin Johnson and Cal Newport.

Steven Berlin Johnson on how to write a book

Steven Berlin Johnson is a science writer and author of several books, including Where Good Ideas Come From: The Natural History of Innovation. In a masterful post about how to write a book, he almost makes the process sound fun. Essentially, he:

  • Reads widely about whatever interests him.
  • Grabs interesting “snippets” from his reading—quotes from web pages, digital books, and printed books (making sure to note the source of each quote).
  • Throws these quotes into one big document with no hint of organization.

Then, when it’s time to write, Steven reads through his collection of snippets and groups them into separate chapters for a possible book. He describes this as working with “pieces of a puzzle that’s coming together”:

Instead of confronting a terrifying blank page, I’m looking at a document filled with quotes: from letters, from primary sources, from scholarly papers, sometimes even my own notes. It’s a great technique for warding off the siren song of procrastination. Before I hit on this approach, I used to lose weeks stalling before each new chapter, because it was just a big empty sea of nothingness. Now each chapter starts life as a kind of archipelago of inspiring quotes, which makes it seem far less daunting. All I have to do is build bridges between the islands.

Cal Newport on writing from a flat outline

Cal writes the fascinating Study Hacks Blog and has several books to his credit. One of Cal’s posts is about avoiding traditional multi-level outlines when writing a research paper. As an alternative, he recommends that you simply:

  • Create a list of topics that you want to cover.
  • Arrange those topics in a logical order.
  • Gather quotes related to each topic.
  • Arrange those quotes to follow your list of topics.

The result is a “topic level outline.” Then, when it’s time to write:

… don’t start from a blank document. Instead, make a copy of your topic-level outline and transform it into the finished paper. For each topic, begin writing, right under the topic header, grabbing the quotes you need as you move along. Remember, these quotes are right below you in the document and are immediately accessible.

This is essentially the same process as Steven Johnson’s: gather interesting quotes, rearrange them, and transform them into something that’s uniquely your own.

Have you ever done something like this? How did it work?

Dictating Your Book Manuscript Won’t Work, and Here’s Why

IMG_1396For years I attempted to create book manuscripts based on transcripts of interviews with clients. In most cases, I failed. This disappointed me and my clients—most of whom liked to talk much more than write.

Eventually I discovered the reason for my failure. It was masterfully explained by Richard Mitchell, author of a wonderful newsletter titled The Underground Grammarian.

In The Leaning Tower of Babel, a book of essays culled from The Underground Grammarian, Richard noted that writing is the medium par excellence for crap detecting, while speaking is frequently a medium for crap producing:

There is a big difference between talk and writing. They are not merely optional ways of expressing the same substance. Talking is normally a social act; writing, unless it is simply copying the given, must be private. It needs…time, solitude, a visible record, and attention.

How we speak, in the press of the moment, is usually the result of habit. How we write, in solitary thoughtfulness, can be the result of choice.

Alas, what I forgot when trying to force books out of rambling speech is captured in the second sentence of the above passage.

The lesson: If you attempt to avoid writing by relying exclusively on dictation and interviews, you risk boatloads of bullshit. As someone who’s read hundreds of thousands of words in interview transcripts, I can verify that while speaking, mostly we are not saying anything. We are doing much to establish rapport and build relationships. But producing ideas? Eh…not so much.

Speaking can work when you want to generate rough material. Just plan to revise it heavily. For creating content that survives the test of time and changes the world for the better, there’s no substitute for the often plodding and sometimes painful craft of editing.

For more details, see this and this. Also check out all 15 volumes of The Underground Grammarian as well as Richard’s four books, which are available for free. Prepare to be offended (possibly) and forever changed.

Your Next Non-Fiction Book—Assembly Required (Part Two)

DSC05735In part one of this post, I posed a question: How do you take a mass of documents that you’ve already accumulated and assemble them into something that resembles the first draft of a book?

This is not an abstract problem. For a recent project, I got a 12-inch high stack of background materials—books, articles, press releases, technical manuals, PowerPoint slides and scattered notes. Plus 70,000 words of interview transcripts.

My assignment: Create a table of contents for a book to synthesize all that stuff.

One of the things that makes this hard is the sheer bulk of THE STACK. It is so palpable, so solid, so intimidating.

Dealing with THE STACK is never easy. But you can take the following actions to reduce suffering.

1. Take inventory

Create a list of what THE STACK contains. Keep it simple. Just list the name of each document and a short summary of it. At this point, don’t make any further decisions about what to do with THE STACK.

2. Shrink THE STACK in your mind

Close your eyes. Visualize THE STACK shrinking to 80 percent, then 50 percent, then 20 percent or less of its current size. This is, in effect, what you’re eventually going to do with the physical stack that reappears when you open your eyes again.

3. Get away from THE STACK

Grab a pen and paper and take a leisurely walk. Go to a place that promotes relaxation and reflection.

Then consider your initial impressions of THE STACK: Did any documents seem especially relevant or especially irrelevant? List them. Did any topics, points, facts, quotes, anecdotes, or images in THE STACK strike you as particularly important or memorable? List those as well, describing them as best as you can for now.

4. Create a table of contents for your book

State the purpose of your book in one sentence. Then turn that purpose statement into your “big question” and a list of smaller-scale, secondary questions that are implied by your big question.

For more details, see this post. This is a heady task, so set aside several hours for it.

5. Return to THE STACK and purge irrelevant documents

You will now reduce THE STACK to submission. Remember that some of its documents will contain few, if any, answers to your questions. Remove those documents now, set them aside, and store them out of sight.

Congratulations. THE STACK has shrunk. This is no small victory. Also remember that the documents you set aside are safe and secure. You can return to them at any time in the future.

6. Go through the reduced stack and scan documents for answers to your questions

Underline, circle, or highlight the passages that contain these answers. If you’re not allowed to mark up documents, then list the name of each relevant document and describe where the passages are located.

You might discover additional documents that lack answers to your questions. Add those to the documents that you’ve stored out of sight. Then savor the fact that the stack is getting even smaller.

7. Capture those answers

Isolate the sentences and images that contain direct answers to one or more of your questions. Capture these sentences and images as direct quotes. After each quote, list the source document.

You have several options for capturing quotes:

  • Get digital versions of the documents in your stack. Then copy and paste the quotes into a new word processing or text editing document.
  • Make photocopies of the key passages and scan them into a document.
  • Type the quotes directly into a document.
  • Write out the quotes by hand on index cards, like Ryan Holiday does.

8. Celebrate

Behold your creation and cheer. You’ve captured the essence of THE STACK in a single document (or set of note cards).

Now you can actually start creating a first draft of your book. Arrange your quotes to follow your table of contents. Add your own ideas. Edit freely.

Most of all, let THE STACK fade from your memory. Yes, it’s likely that you’ll return to it as you keep working on your book. No problem. You know what’s in the stack, and you’ll look for a specific passage in a specific document. When you’re done, you’ll serenely tuck that document away again and return to your book.

Way to go.

P.S. This whole post can be summarized in six words: get key quotes from key sources.

Your Next Non-Fiction Book—Assembly Required (Part One)

mf802The non-writer’s vision of writing a book is that you:

  1. Open a blank document in a word processor.
  2. Type the first sentence.
  3. Type more sentences until you’re done.

If you’ve ever tried to write a book, you know that this is a fantasy.

Chances are that you’ve already created a ton of material related to your book topic, such as:

  • rough drafts of chapters
  • blog posts
  • newsletter articles
  • PowerPoint presentations
  • handouts from presentations
  • transcripts of your speaking
  • white papers
  • reports
  • emails

For good measure, also look for scattered notes that you scrawled on legal pads, index cards, sticky notes, and napkins. Then gather all the relevant article clippings, books, ebooks, and bookmarks in your web browser.

The result is a mass of interesting and possibly useful and supremely disorganized stuff. Your book manuscript is buried in there, somewhere, waiting to be liberated.

The question is: How? In terms of process, your challenge is not to start from a blank slate and fill it with words and images plucked from out of the void. It’s: How do you take the mass of stuff that you’ve already accumulated and assemble it into something that resembles a first draft?

I know that tools such as EvernoteYojimboOmniOutlinerTinderbox, and the artificial intelligence apps from DEVONtechnoolgies can help you gather all that stuff and throw it all into one digital bin.

But the question remains: Once it’s all there, what’s the next step? The answer is about thinking, not tools. It’s about taking an inventory of the underlying ideas in all your stuff, plucking out the relevant ones, and arranging them into a structure that makes sense. And to up the ante, I’d like to do this without expensive, proprietary software that might not exist in a few years.

That’s the problem. The next posts in this series will offer my answers. Please stay tuned.

Structure, Structure, Structure

Approaching CloudsOscar Wilde described one of his writing days: “I was working on the proof of one of my poems all the morning, and took out a comma. In the afternoon I put it back again.”

Yes, he was kidding. Yet Wilde’s description is not so far removed from what some aspiring authors do. They spend hours fiddling with sentence structure and punctuation before doing any serious thinking about why they’re writing in the first place.

In nonfiction “how to” books, basic communication with the reader takes place at the level of structure. You can spend hours choosing words and polishing your sentences to the level of Biblical prose. But if those sentences are combined in a haphazard way and fail to answer the reader’s questions in a logical order, you can disconnect from your audience.

This is a problem you can solve by writing a book proposal before attempting a full draft your manuscript. Your book proposal will include an annotated table of contents—sometimes called an “outline” or “chapter-by-chapter synopsis.”

There is real wisdom in crafting this part of your proposal early on. It is much easier to fix a 2-page table of contents than a 200-page manuscript. As you list possible chapter headings and subheadings, lapses in logic and gaps in content will become painfully obvious.

That’s OK. This is good pain.

The cure is relatively simple. Just spend an hour or two revising your table of contents. This is far less painful than revising page after page of disorganized prose that was written with no overall plan in mind.

Reduce Resistance to Writing By Tackling One Task at a Time

_MG_5191_One of the reasons that I resist writing is the unspoken belief that I have to accomplish a lot in a single session. I easily forget that the behavior we so casually refer to as writing consists of many tasks. Each of those tasks imposes a unique cognitive challenge. I find that writing goes much better when I tackle only one of those challenges at a time.

The challenges I’m referring to include:

  • Defining my purpose—the response that I want from readers
  • Developing my purpose—listing the questions that I’ll answer and objections that I’ll overcome to win that reader response
  • Outlining—listing those questions and objections, arranging them in a sequence that makes sense, and converting them into headings that will appear in my finished piece
  • Researching to find facts, quotes, and anecdotes that support my main points
  • Creating a rough draft by placing those notes under the appropriate heading
  • Editing by reducing or deleting my notes
  • Editing by rearranging notes
  • Editing by rewording notes

When I try to do more than one of the above at a time, my brain starts to hurt.

I’ve been tearing out my hair on a project recently. The reason? I was cycling through all the above tasks in random order and feeling blocked.

The solution in this case was to outline the chapter down to the topic sentence level. This isolated my main points at a granular level and greatly clarified what I was trying to say. With that clarity, I’m able to edit in a meaningful way.

Have you ever used the “one task at a time” strategy? Did it work for you? Do you do something else when you feel blocked? Please let me know.

Confessions of a Retiring Book Editor—Three Things I Wish I’d Known at the Start

work5I’ve been writing and editing books as a freelancer for almost 30 years. When I started, I made a lot of mistakes. Over the years my mistakes improved: I made better ones that led to deeper insights.

I’ll spare you a complete list of my mistakes and what I learned from them. Instead, I’ll just offer the top three. If this saves even one of you from a little suffering, then my career will not have been in vain.

A book is not a “product”

Most of my work has been for corporate clients. They tend to approach a book project as an exercise in product development. Their assumption is that creating a book is essentially the same as creating a car, kitchen sink, air conditioner, or some other thing: You start with standard parts, assemble them with a standard process, and schedule the results. BAM. You’re done.

This is profoundly mistaken. A book—especially a new book—is a unique entity. Nothing like it has ever existed before. Nothing the same will ever exist again. It cannot be mass produced. If I had to compare a book manuscript to anything, it would be a human being who starts as an infant and develops in ways that cannot be predicted.

In fact, a book is sui generis—one of a kind, peculiar. Perhaps it will become profound, or at least useful. But there is no way to know, especially when the writing starts. And failure is an ever present possibility.

One reason for this is that ideas are not things. Ideas are nuanced, complex, and messy. In fact, ideas don’t exist until we articulate them in words, numbers, and images. They are shape-shifters that morph into different entities, hide, and even die if you discover that you have nothing to say.

What’s more, there is no standard way to write a book. The whole enterprise is template-resistant. We not only invent ideas—we also invent the process for creating those ideas. And this must be done over and over again. After all, every writer is different. Every editor is different. Every client is different. Their process of working together is unique and is recreated for every new book project and new set of players.

Corporate clients don’t like this. They issue contracts with due dates for individual chapters and complete manuscripts. I don’t blame them. But the fact is that such deadlines are meaningless until you’re well into the writing process. You have to be willing to rethink and revise and reschedule. And that’s a hassle.

Writing is iterative

Writing instruction in schools and universities has improved since I left formal education. Teachers are now encouraged to present writing as a process of discovery. This means being willing to write a rough draft and revise it many times.

In the corporate world, no one buys this. Clients might allow you a couple of drafts. But even this can be regarded as a sign of failure. Instead, you’re rewarded if you “nail it” the first time with only one draft—as if that’s a virtue instead of a path to superficial thinking and shoddy results.

The smallest meaningful unit of revision is the entire manuscript

From a practical standpoint, this is my biggest headache. Many clients want me to produce a table of contents for a book and then submit individual chapters—in order, in final form—that will immediately go into production.

This is crazy-making. It denies me the chance to delete chapters, add new chapters, rearrange existing chapters, and revise earlier chapters in light of what I learned while writing later chapters. The ability to do these things is essential to my work. Taking them away from me is like asking me to play baseball without a bat and glove.


I wish I had sure-fire solutions to the above problems. The best you can do is take the time to develop a book proposal before committing to due dates and results. This won’t eliminate headaches, but it will lessen them. And that means a lot.

Why Deepak Chopra Worries Me—The Tension Between Self-Help and Spirituality

DSC02390I’ve met several people who read widely in the “mind-body-spirit” category and want to write a book of their own in this genre. While I laud their intention, I also offer a gentle warning.

Too many self-help authors treat the sacred teachings of the East—including the meditation traditions of Buddhism and Hinduism—as a vast smorgasbord from which they can pluck ideas at random. This leads to fundamental problems with their writing.

Case in point: I remember being so excited to read The Seven Spiritual Laws of Success by Deepak Chopra. Now I see it and squirm.

The problem is that he glosses over some huge cultural tensions. On the one hand is the Western gospel of success. One the other is the teaching of the meditation masters. These are two different landscapes of discourse. And the tensions between them are tough to resolve:

  • The popular self-help literature is largely about becoming happy, which is usually defined as setting and achieving goals.
    • Meditation is about being content—a serenity that is already present and does not depend on achieving any goal.
  • Self-help writers often equate happiness with pleasure, which is impermanent and conditional.
    • Meditation teachers talk about serenity, which is stable and unconditional.
  • Self-help writers load us up with concepts, formulas, and strategies.
    • Meditation teachers talk about nirvana, which transcends all concepts, formulas, and strategies.
  • Self-help writers pose a question: What do you want?
    • Meditation teachers ask: Who does the wanting? Who are you?
  • Self-help tells us to imagine what could be and then take planned action to produce it.
    • Meditation teachers ask us to notice what is and then act spontaneously.
  • Self-help creates activity.
    • Meditation creates stillness.
  • Self-help creates goals.
    • Meditation creates goalessness.
  • Self-help tells us that paradise is planned and created.
    • Meditation tells us that paradise is here, now, and simply recognized.

Both perspectives are useful. And, they contradict at key points. When we forget this, we walk blissfully unaware, straight into land mines of paradox and potential confusion.

Making Time to Write—Two Strategies from Bob Pozen

pozen_HBSAre you too busy to write? Before you answer, consider Bob Pozen.

Bob Pozen is busy. As chairman emeritus of MFS Investment and senior lecturer at Harvard Business School, he essentially works 2 high-profile jobs. At the same time, he’s a prolific writer. In addition to producing an avalanche of articles, he wrote Too Big To Save? How to Fix the US Financial System and other books.

How does he get all that writing done?

Pozen revealed his productivity secrets in a series of interviews conducted by Justin Fox for the Harvard Business Review blog network. These led Pozen to write yet another book, Extreme Productivity: Boost Your Results, Reduce Your Hours.

Focus on thinking—not time

Fox asked about how to write quickly, and Pozen’s reply blows me away. He turned the question around:

A lot of people confuse a thinking problem with a writing problem. In order to write quickly, I need to see the line of argument very clearly. If I don’t fully understand the line of argument, I cannot write even a paragraph. My brain won’t let my pen move.

In order to spell out the logic of the argument, you need to compose an outline before writing. Only by playing around with an outline can you get comfortable with the key steps in the argument. For an article or a speech, an outline does not have to be long or detailed. Just the four or five key points, with a few sub-points under each.

True, a book is more complicated than an article. For books, Pozen writes a detailed outline and then sends it out to reviewers before drafting chapters. The strategy is essentially the same—start by thinking clearly through the whole of what you want to say.

See the first draft as a process of discovery

Even though your outline (table of contents) represents a complete prototype for your book, you’re going to learn a lot more when you flesh it out into a series of chapters. As Pozen said:

After you clarify your thinking by writing an outline, you’ve got to be willing to write a first draft that is rough. Most people feel they have to write a really good first draft and that’s why they get writer’s block. In many cases, it’s only when you actually finish your first draft that it comes to you how the whole piece fits together.

That short paragraph unpacks a lot. First comes one the most common pieces of writing advice—let the first draft be rough. Keep your expectations low.

Then Pozen adds something profound and easy to forget: When creating a first draft, you’re still finding out what you want to say. In fact, we could justifiably call this process something other than “writing”—like creating a “discovery document” or “expanding the table of contents.”

Don’t even say that you’re “writing a book” until you start the second draft.

Semantic games? Try it and see what happens.