Outlining Your Book: Three Crucial Steps

When you sit down to write a book you and I can waste a lot of time, if we don't take time to outline

But what are the elements involved in outlining? And how can we make sure we don't make any silly mistakes?

If you're about to write a book or plan to be an author sometime later, this information is for you. But even if you've already published books, you'll be amazed at how this information speeds up your process and gets better results.

In this episode Sean talks about

Element 1: How many points do you cover in your book outline?
Element 2: Why deconstruction is important.
Element 3: Understanding the purpose of the book.

Read online: Outlining Your Book: The Three Crucial Steps

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Around the start of 2010, I was very upset with myself.

I'd pre-sold a workshop and as I always do, the notes for the workshop are sent to the attendees a whole month in advance. Since the workshop was being held earlier in the year, I had been thinking about the notes right through my summer break in late December and early January.

Uniqueness is a pretty difficult topic and I needed to find a way to ensure that everyone—without exception—got the concept of uniqueness and was able to implement it. The only problem with writing the notes, was that it seemed like the notes were going to be at least 200 pages long.

200 pages is like a security blanket for a writer

In the mind of a writer, the chunky volume of notes seem to suggest you have something important to say. And yet my wife Renuka isn't a big fan of a ton of notes. “Why can't you write fewer pages?” she asked me as we were sitting at the cafe. “Why can't you get the same point across, so I don't have to read so much?”

A pointed question like this is truly frustrating for me because I know it's easier to fill a book with a ton of information. But a book, or notes in this case, need to be Spartan. They only need to have enough pages; just enough knowledge for the client to get a result. They don't need to be padded or filled with words no one needs. And this meant I had to go back to my outline several times.

When writing a book, the most difficult task isn't the writing

Distilling the ideas down to simplicity is what gets in the way. I have to force myself to leave the office, sit at the cafe for hours at a time, with no Internet connection. Monday's draft gives way to Wednesday's, and will be supplanted by Friday's draft. Sometimes it can take a month of drafts to get my thoughts together.

Except it was already January. The clock was ticking closer to my deadline. I had to make sure I had the book going. Which is why you, and I, we both need an outline.

So how do you outline a book?
What method should you use?
What if you can't write a lot and can only manage a few pages? Should you give up?

Let's explore three elements of book outlining to get us on our way:

Element 1: Why you should ideally cover just three points.
Element 2: Why deconstruction is important to get you going
Element 3: Understanding the purpose of the book.

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Element 1: How many points do you cover in your book outline?

When you think of a topic like “presentations”, what comes to mind?

Let's make a list, shall we?
– Creativity
– Crafting stories
– Simplicity
– Delivery
– Audience connection
– Engagement
– Displaying Data
– Creating Movement
– Time Keeping

Those points above represent a tiny list. If you were to look through the books on Amazon.com alone, you'd find at least fifty, possibly a hundred, even two hundred and ten topics on the singular topic of presentations. It's at this time that a novice or unthinking writer decides to do it all. He or she decides to cram as many items as possible into a single book, just to make sure nothing is missed.

Take watercolours, for instance

Back in 2010, I was pretty hopeless at watercolours when the painting bug struck me. How hopeless is hopeless? I painted for three months faithfully following the instructions of my teacher, Ted. After three months, the area had an auction of the artwork. My painting came up on the auction block.

The auctioneer started at $30. No takers

$20? Wait, auctions are supposed to go up, not down.

But there was the painting at $10, and still no buyers in sight. Now that you'll have to agree is a hopeless situation. Anyway, to avoid such a high level of embarrassment in the future, I decided to take watercolours a lot more seriously.

I tramped down to the library and came back armed with at least a dozen books on the subject matter. As I opened book after book, a similar scenario unfolded. Every book seemed to feel the need to cover all the possible topics under the broad umbrella of watercolour.

This is the kind of mistake you want to avoid as a writer

The journey to outlining a book or just about anything—a book, an article, even the weather report—is better served by working three elements; three main topics and then digging deep into the sub-strata of every one of those topics. Ironically, though, you have to start with the entire mess. 

You have to begin your journey by being reasonably crazy and listing everything. Which means you've got to roll out two steps.

Step 1: List all the points you can think of
Step 2: Choose three points

Take for example the topic of “pricing”

If you were to gaze deep into the crystal ball of pricing, you'd be sure to run into dozens of topics and angles. Covering every possible scenario, even at the brainstorming stage should drive you crazy. Well, let it drive you crazy. Writing a book needs to start with a brainstorm, long before you get to the outlining stage.

So let your imagination go on that rodeo as you list everything you could cover. 

An exhaustive list is not a bad thing. It demonstrates how much you know and how much you can cover in the future. However, once you're done with that list, it's time to pick the three elements that will go into your book. You have to wiggle your way into Step 2 and choose three points.

The problem with Step 2 is deciding which points to choose

You'd probably think it's crazy to choose any random points, but that's usually what I do. Take the “Black Belt Presentations” book for example. I didn't set out to write a series of books on the structure of a presentation or webinar. 

I set out to write a single book. And when we look at the huge list we can muster from a single visit to Amazon; I decided to simply choose the three elements that I considered to be important.

And so we had:
1: Controlling the visual aspect (how to create stunning slides)
2: Controlling the structure of the presentation (how to build the presentation with amazing flow)
3: Controlling the audience (why a great presentation can be ruined if you're not prepared for the reality of an audience).

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When outlining, take on the role of a GPS. Sure there are a thousand points to cover, but it's easy to get lost. Instead, cover just a few points, ideally no more than three main points.
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Were there more topics to cover?

Sure there were. Would I cover it? Maybe in another book, a series of podcasts, articles, etc. But as a writer, creator, weather reporter, you can't really go digging into every single cloud or that spotty bit of sunshine. You have to make a decision to drop stuff. 
To take a simple analogy, think of a sculptor. Or rather a dozen sculptors all with similar blocks of marble.

The job of the sculptor is to remove the bits that don't matter so that you can reveal the sculpture that does matter. Yet, when you look at the finished work of a dozen artists, you'll notice they all end up with different types of sculpture. 

Given the same topic, e.g. presentations, you have to get rid of all the sub-topics you can't possibly cover and stick with just three.

Three? Not four? Or five?

I've got “The Paradox of Choice” by Barry Schwartz sitting on my desk. First written in 2004, it's gathered a bit of dust, but when I open the Table of Contents, what holds 250-odd-pages of the book together? It's the topics—four, not three.

1: When we choose
2: Why we choose
3: How we suffer
4: What we can do.

And nestled under those four categories are what Schwartz needs to say. Even though you can clearly spot ten, wait, eleven chapters and one prologue, they're still magnificently constrained by the limitations of four topics.

When you look at The Brain Audit, you don't quite see that in the Table of Contents, do you?

The Brain Audit is split up quite clearly into seven chapters. And yet there's an overlying structure to the book. The first three chapters are about attraction. They're solely dedicated to getting the client's attention. 

The next four chapters are all about risk. It's what causes the client to back away, to get all hesitant, even though they seem to be so interested in your product or service.

But what if you don't have such clarity of vision?

How are you supposed to know that one topic will seamlessly fit into another? The reality is that you don't need any such seamless fit at all. Three random topics can fit together. To demonstrate this, um, magic trick, let's take that list we created above. Let's first randomly take the first three topics.

– Creativity
– Crafting stories
– Simplicity

The three topics work together, don't they? So let's take the next lot.

– Delivery
– Audience connection
– Engagement

That works too, doesn't it? Let's move to the third lot.

– Displaying Data
– Creating Movement
– Time Keeping

You may feel that timekeeping may not require an entire chapter. And if that's the way you feel, then simply get rid of the topic, and slide in one that makes you feel more comfortable.

For example:
– Displaying Data
– Creating Movement
– Audience connection

Writing a book may seem like a daunting and reasonably frustrating experience

An enormous amount of frustration bellows forth from the need to cover everything in sight. Instead, if you were to cover three topics, almost any three topics, you could seamlessly stitch them together to create a fantastic outline.

You still have to do a fair bit of work to get the book written, but the battle is won or lost at outline stage. Train your outline to sit, beg and play dead, and you've already vaporised away the first—and biggest headache of all.

This takes us to the second bit where you outline the personality of your book

To get on this fascinating trip of structuring the personality of your book, you have to dig into a whole bunch of books you love. It's time to use the power of deconstruction to get going.

Let's deconstruct.

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Element 2: Deconstruction—How To Systematically Outline A Book (So You Can Get It Off The Ground)

Imagine you're the emperor in a far eastern land.

And your son, Kintsukuroi (pron: khintz-ku-roi) is about to go through the ceremony of investiture. The bowl is the most important symbol of this rank being given to the young prince.

And yet, the king opens his cabinet to find the magnificent bowl broken into a hundred pieces. Broken hearted at the wanton destruction of this incredible piece of art, the emperor retires to his private chambers to share his sorrow with his son.

The night passes quietly, but in the morning there's a huge commotion.

The cabinet of treasures has been broken into and not only have the pieces of the bowl disappeared but also the bejewelled crown for the prince, which was to be used for the investiture ceremony. What's worse is the thief was seen running towards the prince's quarters. Could the guards break down the door? Why was there smoke coming out of the prince's quarters?

The mystery was solved the next day when the bowl reappeared, whole again, but glistening with veins of gold where the cracks had been. And the prince appeared at his investiture ceremony later in the day. Except he had a thinner crown, depleted of much of its gold.

Kintsukuroi means ‘to repair with gold’ in Japanese, and is the art of repairing pottery with gold and understanding that the piece is the more beautiful for having been broken.

When creating the outline of a book you have to deliberately break, or deconstruct the work of others, so that you can engage in Kintsukuroi, and reconstruct your own book in a way that's far superior.

And that's exactly what I did back in 2002 when I first started writing the earliest version of The Brain Audit

I was brand new in marketing and writing just 16 pages of The Brain Audit took me well over a week. Even the introduction derailed me quite a bit. So I turned to a book I loved a great deal called “Don't Make Me Think” by Steve Krug. 

His introduction seemed to be so un-stuffy, so well put together. And he had a ton of graphics in his book. Right then and there I decided my book would have a similar tone of voice and style.

When outlining your book, it's easy to get caught up in the construction of your own words and pages. And yet, it's pretty important to go through at least six-eight books that you love, if only to understand the underlying structure.

Take for instance most of the Psychotactics books or courses

There's a structure to the book that you may have noticed, but not necessarily paid great attention to.

– It starts off with an introduction.
– The introduction is followed by three main topics.
– Every topic goes deep into the sub-topics.

And as you wander though the pages of the book, you'll run into cartoons, captions, stories, examples, fly out boxes, summaries, a food recipe—and so on. 

This is the underlying structure that makes the book so easy to read.

It's the powerhouse that pushes you forward, making sure you get to the last page. Compare this with a book that has no summaries, no visuals, no captions and examples that are always harping about ginormous companies like Amazon and Apple.

You get the idea, don't you? When you deconstruct a few of your favourite books, you get a wish list of what you'd like the reader to experience in your own books, don't you?

You've gone through the act of Kintsukuroi

The books you looked at were already quite impressive by your own reckoning. That's the reason why you chose them in the first place. But then after you've broken them apart, you get to reconstruct them in a way that's more beautiful and more suited to you than ever before.

And this structural break and remaking process is what helps you put your information under a structural format that you can keep and evolve over the years. When you're outlining a book, it's easier to put pieces of content where there's already a category or space. It's a lot less intimidating when you know what needs to go where in the book structure.

Structural inspiration comes from many places

I love the music of Sting, and in one particular concert he talked briefly about the inspiration behind several of his songs. For instance, did you know that “Englishman in New York” is not Sting singing about himself? In the video it appears as though the song is about Sting, an Englishman, but in reality the song is about famed gay author Quentin Crisp and his experiences as an outcast.

When I first heard that little bit of information, I was quite tickled. And so I decided to add a little story about how we “wrote our books”. Since then the structure of a Psychotactics course or product has included “the making of this book” that includes photos and a little story.

But if I copy the structure, won't it look similar?

Did you know that my introduction and illustrations were influenced by “Don't Make Me Think?” Of course not, and even now if you were to hold The Brain Audit and Steve Krug's book side by side, you're unlikely to find too much of a resemblance. 

The key isn't to make an identical copy.

Remember the procedure? You're breaking first, then reattaching it together. There's a bit of additional input going into the structure. Whether the structure comes from you or from another source, it all helps to create that Kintsukuroi moment. Construction after deconstruction.

This is the kind of deconstruction you want for your book as well

You could see it as a sort of template for all books you create in future. What makes it truly beautiful is that the act of breaking up the structure of other books ends up with a stunning new creation. It's truly Kintsukuroi and helps create a powerful outline structure.

We worked our way through creating just three topics, deconstructed and reconstructed the structure of our book, but finally it's down to purpose. Why are you writing the book? Is it just to put words on paper, or is there some other reason?

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Element 3: Purpose

Usually from December 20th to Jan 20th every year, I take a summer break.

The days consist of no e-mail, endless episodes of detective series on Netflix, biographies and beer. Eventually, December gives way to January and New Zealand (and I) wake up from our month long vacation.

To ease myself back into work mode, I start reading business books. And this year started out with an outstanding book called “The Content Trap” by Bharat Anand. Just leafing through the introduction takes you well past 30 pages and yet every moment of the introduction is gripping.

But what is Bharat Anand's purpose?

This is the question most writers need to ask themselves before sitting down to outline their books. Is the book meant to create consulting? Are you expecting to improve your profile? Would you hope to do a speaking tour as a result of your book becoming a bestseller? Would companies hire you to solve their problems? And would it involve big business or small firms?

In the case of the “Content Trap”, my perception was that the book was aimed at bigger companies

The examples within the book were amazing, but there they were: Amazon, the Scandinavian newspaper publisher Schibsted, The New York Times, the sports marketing giant IMG and Harvard Business School's own content management system.

These examples leave me and most other readers in a sort of trap of our own. We have all these utterly outstanding examples, but all of them are companies that are high and mighty. Even if we were to admire the sheer depth of the learning, how would someone like you or me put this information to use?

And this is where the purpose comes right in

You need to be clear about why you're writing the book. In Anand's case, he's got a great idea and scintillating data to back up his concept, but it falls apart at the seams because there's no way to use it.

Could it be that the book is designed to give potential clients an idea of what's possible? Could it be that they then call the author in for extensive consulting? Many books are written with the goal of getting consulting in mind. Could this be one of them?

When I sat down to write an outline, I wasn't always clear about the goal

The early years saw me create sparse outlines and fill content into the early books. This was my way of battling my seeming insecurity. I didn't see myself as a marketing person and saw myself as a cartoonist.

The more pages I had in a book, I convinced myself, the less I had to worry about refunds.

It doesn't help when some early buyers, and we're going back to 2003 or so, said they were returning the books because there were too few pages. 

Back then, most of the world was still walking into bookstores and stepping out with $20 hardback books. And there we were, selling a PDF for $67 that consisted of fewer than 20 pages. Hence the need to “fix the book” by adding a tonne of material that may or may not have been needed.

Today, when I outline the book, the main goal is to get a precise result

If you buy the book on presentations, you could be woken up at 3 am and still be able to put together a very compelling presentation from the ground up. If you spent your hard earned money on the information products course, you'd find an incredibly well thought out template on how to create info-products.

Whether it's photography, article writing or landing pages, the goal is well-defined before I start to write. And this is something you should do. It seems like such a tiny, inconsequential part of the outlining process and yet it's crucial.

What's the end point when the book comes out?

Is it to get you more consulting?
Is it to get you more fame?
Is it to create a permanent source of income and nothing else?

Knowing the end point makes a difference to the examples you give and how you structure your book. The end in mind, it's sometimes called. Knowing where you're going. It applies to everything in life, but especially when you're outlining a book.

Once you know exactly where you're going, you can focus your energy better than ever before.

The Three Elements Needed When Outlining Your Book are:

Element 1: Why you should ideally cover just three points.
Element 2: Why deconstruction is important to get you going
Element 3: Understanding the purpose of the book.

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