Outlining My Feelings On Outlining

outlineA new list member asked about outlining; how to, more than why to (or why not to.)

Below is an enormous excerpt from my cute little book Getting Your Book Out of the Someday Box. While it describes my nonfiction writing process, it’s really an information-gathering-and-sorting process, which, in a way, is what outlining is about.

If this raises more questions than it answers, as I fear it will, ask and ye shall receive.

An Outline of My Writing Process (Which You Can Use as an Outlining Process)

Gather all the data you have (either the information, or just the questions, references, etc.) regardless of format:

  • print
  • blogs, emails, website
  • audio and video
  • what’s in your brain (for now, jot just enough notes to trigger what you know, but haven’t written or recorded in any format yet)

For each item, consider a couple of categories it might fit into. Write 3×5 cards for each. Start putting stuff into categories.

Some categories will have nothing in them. This may mean you need to create the content for this category. Save this card for step 3. Some stuff, you just won’t be able to decide which of two categories it goes in. Perhaps the categories should be combined? Some categories will be huge. Drill down and create subcategories.

This will be an ongoing process. Don’t pretend you’re going to organize your thoughts and never look back. Get this 80% of the way done and move on.

Order: is there a logical flow to the categories? If not, are there any dependencies? Put stuff in order where order exists.

Where order does not exist or matter (does the chapter on Bob Dylan have to come before the chapter on Tom Petty? order probably doesn’t matter in some cases) choose, arbitrarily. You can always change it later.

There; we’re ready to fill those holes.

Identify the Gaps

Next we need to identify the gaps: the ideas and concepts that are incomplete or missing.

Once you’ve got all your data on the table, categorized into chapters and/or sections, you’ll see some obvious gaps; things you know should be there, but aren’t, or things you didn’t realize were a logical part of this book.

There are two options—you should be very aware of what you’re doing at this phase to avoid going down the wrong path.

It’s easy to add more content, filling the gaps. This might be a good option if your content is easy to carry around in one hand while you carry your laptop in the other.

If, on the other hand, you have to stack two moving boxes to carry all your notes, perhaps a better plan would be to find a break point where you can create a natural feeling of conclusion or summary and end the book there.

You do not have to write a long book. In fact, a short book is much better. More people will actually buy it. More of those who buy it will finish it.

And then, you can turn the rest into a second book. And a third. And so on.

Once you’ve decided where the gaps are in the content you intend to use for this book, identify what goes there. You’re not writing it now, just giving it a label that’ll help you remember it later.

Well, not much later. In fact, that comes next.

Fill the Gaps

Now we prioritize the missing bits, and create them. This is the piece most of us think of as “writing a book.”

Priority means “first in some meaningful way.” It might be chronological, but usually isn’t, not directly. It might be the part that comes easiest. Might be what naturally comes before the other.

In the end, what you’ll write is what you should write. Forcing yourself to dig into the toughest section is madness—doomed to failure.

Start with the bit that’s falling-off-a-log easy. Knock something out in an afternoon; that one little bit that connects A to C.

There. Doesn’t that feel good? And now, kill off the next easy bit.

Before long, you’ll have nothing left but that big hairy knot you’ve been dreading. Except, now, you’ve got all the success under your belt and it’s not so scary. Besides, it’s the last thing. You’ll dig in and love it.

All that other stuff you’d created, the “stuff” between which these gaps fell? Now’s the time to get it transcribed, or add an intro/outro or connecting bit between this and the new stuff.

Questions? Thoughts? Jelly doughnuts? Put ’em in that comment box below and we’ll palaver, pardner.

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