July 14

If you have a huge archive of content, what’s the best way to organize content into a book?


You have an archive of blog posts, dozens or hundreds of podcasts, notes from speeches and workshops, and bits and pieces of thoughts scattered around everywhere. How do you bring it all together to form a book?

Let me tell you my philosophy: A book is its own type of writing. If you want this book to have a powerful, long-lasting effect on the reader, it cannot simply be an ordered accumulation of your favorite stories/posts/interviews/speeches. I know that some people have published books like that (and sold a lot of copies!), but I believe that these sort of “best of” books do not have a long-term impact on either the reader or your own platform.

When you’re writing a book, you need to keep in mind two things:

  1. Your own backstory, how you came to be where you are now, and
  2. Your reader’s transformation, how you can help her get from where she is now (stuck) to making progress (taking action)

A book is a weaving together of these main transformative journeys, your own and your reader’s. About 25% of the book will be your journey, and the rest will be your best wisdom, insight, stories, and pieces of advice to help your reader on her own journey. This 75% of the book doesn’t have to be prescriptive or “how to.” It can be inspirational and just painting the vision for her of what her life could look like when she’s transformed this area of her business, health, money, relationships, or whatever your topic is.

So, a book is not just an order of content you’ve already produced. It’s actually a crafting of a new type of content with a distinct purpose: to take the reader on a transformational journey from stuck to action.

When you organize content into a book, start by bringing all the bits and pieces into one place.

Bring all your digital notes into one digital folder on your desktop or one folder in Evernote or one project in Scrivener. And bring all of your paper jottings into one physical location, file folder, or box. You need to feel that peace of knowing that all of your written thoughts and ideas are collected into one place, as best you can.

I do not recommend spending too much time actually organizing these digital and physical writings. You could easily spend six months copying and pasting bits of documents from one to the other and shuffling pieces of paper from one folder to the other and still not feel the least bit clear on the direction of your book.

Instead, just spend a week or so reading through what you’ve written previously. Resist the urge to categorize or organize too much. Trust that your brain is creating associations and neural connections, even if you don’t totally grasp what those are, just yet. (For more information on how your brain does this magical, near effortless organizing, read Mark Levy’s Accidental Genius).

Then, spend about a week free writing.

If you’ve followed me for long, you’ll know that I believe free writing is an absolute game changer. I’ve written more extensively about free writing, and please do read that post. But, for the moment, let’s suffice it to say that once a day, you should sit down and simply write out your thoughts about your possible book topic.

Don’t put a lot of pressure on yourself when you’re free writing. Allow it to feel like an experiment or an exploration. You’re writing to see what ideas pop into your brain, and here’s how I recommend you do it:

  1. Set a timer for 5, 10, or 20 minutes.
  2. Bring your book topic to mind (very generally, not writing the introduction, just broadly what you think you’d like to write about).
  3. Write as fast as you physically can (keep your fingers moving, no backspacing, no spelling corrections, just keep writing or typing).
  4. When the timer rings, stop.

This may not seem like a magical process, but I promise, it is. Your brain has a near-miraculous ability to create associations and connections, and you are more able to access those neural pathways when you’re not consciously judging your own thoughts.

Go through those four steps every day for five days or so.

Finally, you can start organizing your thoughts.

You’ve allowed your thoughts to connect and create associations through the free-writing process. Now, it’s time to organize them. Do a brain dump of everything you’d like to include in your book—every story, idea, piece of advice, wisdom, insight, and ah-ha moment that you’d like to share with your reader about your topic.

You’re essentially writing a long, unordered list of ideas, and it’ll be at least four or five pages, maybe more. Once you’ve got it all down on paper, now you can start to organize.

Cut and past ideas, grouping like ideas with like. As you see specific groups emerging, maybe put a sub-heading on them. As you see related groups, copy/paste them next to each other, and maybe put a chapter heading on them.

You’ll notice that we’re creating a bit of an outline, but I like to create it from this ground-up, organic way. I call it a rough organization because it’s a lot of ideas, roughly organized. ;) This doesn’t have to be perfect, just barely organized enough that you feel confident that there’s a book in there, somewhere.

What about all that content you’ve already written? Now, it’s time to organize content into a book.

Okay, I’ll let you in on the magic of this system. If you’d tried to sit down with what you’ve already written and impose a structure on that previous content, it would feel like trying to get stray cats to stand in a line. Your thoughts and ideas would run all over the place, chasing rabbits down rabbit holes, and you’d spend months banging your head against your keyboard.

With this method, we’re allowing your brain to do most of the organizing for you. You’ve already got the ideas in your brain—you wrote/spoke all that content to begin with!

Now that you have this rough organization, you can bring the relevant pieces of content over and slot them in, where they should be.

From here, you can go one of two ways.

  1. You can leave your previous content set aside and just start writing fresh. Use your rough organization as a reference, and just write straight through. Start with the first idea in the first chapter and write it out. Then go on to the second idea, and just keep writing, all the way through your long list of a rough organization. After you finish writing the fresh first draft, then you can return to your previous content and add in the bits that enrich your first draft.
  2. With your long list of a rough organization, you can sift back through your digital files and written notes and pull out the relevant bits. You could pop them into their own folder, for future reference and just note on your rough organization the areas where you have a previously written piece of content to copy/paste in. Then, start writing your first draft from the beginning. Start with the first idea in the first chapter and write it out. When you get to a part in your rough organization that indicates you already have something written, go back to that special folder and copy/paste it into the first draft.

What you’ll notice is that you’re allowing the rough organization to guide the structure of your book, and that will make all the difference in helping your book to feel like one, cohesive, transformational narrative.

Okay, go find all those documents and bits of paper, bring them together, and let the fun begin!

What content are you working with? Blogs, podcasts, speaking notes? Do you have any other systems that work well for organizing your content? I’d love to hear about them! Leave a comment below.


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