Are Your Writing Deadlines Meaningless? (Part 2)

 DSC03551-BWFor decades I’ve struggled with scheduling book development projects—especially first editions of first books by new authors. Now I see the reason: many of these projects defy scheduling — and for good reason.

I explored this issue in Are Your Writing Deadlines Meaningless? Recently I found confirmation in a nice piece by Wyatt Jenkins about The Downside of Timelines. His post is about software development. Mine is about book development. Same deal.

What makes timelines so problematic for complex creative projects — such as producing 40,000 to 100,000 compelling words on a timely topic?

The main reason is that such development is not linear. Creative projects are often not a matter of setting a clear vision of the result and taking a straight line to implement it. Instead, developers typically stop mid-project to assess what they’re doing. And they may well conclude that the project needs to be significantly revised or even scrapped.

This is not a mistake. It’s called learning. There are some things that you simply cannot know until you get your hands dirty and start making parts and assembling them. Reality is messy and defies our attempts to beat it into orderly submission.

This is hard to explain to people who like to craft Gantt charts and schedules. I empathize with them. I like rules and order, too. But makers know that the process is full of surprises, detours, land mines, lions, tigers, and bears. People who write books, for example, might discover that they have nothing to say.

As Wyatt Jenkins points out, there are ways to hold creative people accountable other than chaining them to meaningless deadlines. My favorite strategy: take a cue from Getting Things Done by David Allen and commit to take the next action that will move the project forward.

In book development, for example, your next action might be to draft a table of contents or write the overview section of your book proposal. Either document is 2-4 pages—500 to 1,000 words. Such tasks are crucial and still small enough to meaningfully schedule and budget. Best of all, they’ll teach you a lot and bring you substantially closer to a finished manuscript.

P.S. There are exceptions to what I’m saying. For example: you’ve already got a book published and are doing minor or manageable updates for a   new edition. Then it makes sense to pull out your Gantt charts and schedules and abide by them. The more predictable a project, the more that tight scheduling makes sense.

P.P.S. I tweeted about Wyatt’s post:

Scheduling a book project? “You can’t schedule substantial complexity” [@wyatt_earp_]

And he replied:

Rephrase: it’s a ton of effort schedule? Additionally, output of “a schedule” is less valuable than output of “a working product.”

Excellent point: the time spent on detailed bids can instead be used to make a minimum viable product.

James Altucher on Writing, Publishing, and Becoming an Idea Machine

main-thumb-288636-200-fhgkbzymvtxxzdwnhcyyahhktlfzazijDo you know about James Altucher, author of Choose Yourself, The Power of No, and other books? Besides writing books, he’s blogging, podcasting, and doing just about everything else with a quirky voice that will immediately turn you off or win you over.

Today I want to highlight a few of James’s insights on writing, publishing, and idea entrepreneurship. Check out the following.

Can You Do One Page a Day?

Gene has been an adult for almost 25,000 days. He writes a page a day. A page is about 300 words. A paragraph or two. Can you do that? 25,000 pages. About 80 books worth of pages. Gene ended up writing 50 published novels, including many bestsellers and award-winners.

The Ultimate Guide for Becoming an Idea Machine

IDEAS ARE THE CURRENCY OF LIFE. Not money. Money gets depleted until you go broke. But good ideas buy you good experiences, buy you better ideas, buy you better experiences, buy you more time, save your life. Financial wealth is a side effect of the “runner’s high” of your idea muscle.

How to Self-Publish a Bestseller: Publishing 3.0

My most recent book, “Choose Yourself!” sold 53,000 copies since its release on June 3 [update December 30 – just hit over 100,000 copies], hit the Wall Street Journal Bestseller list, was No. 1 on Amazon for all non-fiction books for a few days and is still flirting with No. 1 in its various categories. This post is about what I did differently, why I did it differently, and how I think anyone can do this to self-publish a bestseller. I describe all the numbers, who I hired and why, and how I made the various choices I did.

33 Unusual Tips to Being a Better Writer

Write whatever you want. Then take out the first paragraph and last paragraph…. Take a huge bowel movement every day…. Bleed in the first line….

Why “50 Shades of Grey” Is Great Literature

Art can happen in every moment of your life. It’s not about colors or words or message, it’s about your personal authenticity this moment. You can be an artist driving a bus if you do away with conventionality and become the individual without masks, without jealousy, without intrigue, without hate.

How to Write a Book

Make an outline, it will help. An outline will allow you to jump around and work on those areas that interest you at that moment.

And just for fun:

The Ten Layers of Absolute Freedom

The Ultimate Cheat Sheet for Reinventing Yourself

An Ode to “How-To” Books

DSC_0517Most of my work involves writing and editing instructions — otherwise known as “how-to” books and articles. When telling people this, I used to feel a quiet inferiority.

This was especially true when I talked to “creative writers”— novelists, short story writers, and poets. When in the presence of people who were attempting vast and profound narratives, I felt almost embarrassed about writing how-to materials. They smacked of something utilitarian, “vocational,” and pedestrian — the artistic equivalent of working the night shift at a convenience store.

Well, I no longer feel that way. And if you’re writing a how-to book, you don’t have to, either. Following are three good reasons.

Timeless Usefulness

The label “how-to” can apply to instructions for doing anything that human beings consider intrinsically valuable. We can write instructions for ways to create health, wealth, happiness, knowledge, love, and even enlightenment. In fact, many best-selling nonfiction books are about these topics.

For example, one of my favorite books is Zen and the Art of Motorcycle Maintenance. It was written by Robert Pirsig, a former technical writer (creator of instructions). This is a riveting book about how to cultivate Quality, how to stay sane, how to love your children, and how to realize your inherent peace of mind. To me, large sections of this book still stand as models of instructional writing.

We can take this up a notch and even say that society hinges on giving and receiving instructions. As Richard Saul Wurman points out in his book Information Anxiety:

You could argue that the motivation of all communication is the giving and receiving of instructions. Certainly the sum total of activity in the workplace involves the giving and receiving of instructions. As parents we are synonymous with instructors. And even in our social relations, we are communicating or “instructing” our friends and relatives as to our thoughts and concerns.

Beauty

“How-to” books can be beautiful as well as useful. Have you ever read a set of instructions that helped you accomplish a task and did so without a needless word or an unnecessary step? This sparseness can evoke the simplicity and grace of a painting by Mark Rothko, a haiku by Han Shan, or a jazz guitar solo by Jim Hall.

Market Demand

The market for instructional books — shelved under the how-to, business, and self-help sections of your local bookstore — far exceeds the demand for literary fiction and poetry. Don’t get me wrong: I enjoy fiction and poetry as much as anyone else. But if you want to earn money from writing and editing books, then “how-to” literature offers its own practical rewards.

In short, nothing is more important than good instructions. As how-to writers, we are engaged in a vocation that has its own esthetic and satisfies a basic human need. All writing is creative, and our work fuses the practical and the beautiful. We do something unique and useful, and it is a great way to earn a living.

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.