← The Art & Business of Writing Podcast with Nicolas Cole
The Art & Business of Writing Podcast with Nicolas Cole
How To Outline A 60,000 Word Book In 24 Minutes
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In the next 20 minutes, I'm going to show you how to outline a 60,000 word book from start to finish. And no, we're not just going to ask ChatGPT to do it for us. And no, you don't need to be some prolific genius level writer in order to do this. The outlining method that I'm going to share with you is how I outline all of my books. And I have self published and written 10 books at this point. But it's also how I outline all of my social content, my YouTube videos, newsletters, anytime I'm sitting down to write anything. This is the method that I use. And once you understand this framework, you will never write and outline your writing the same way ever again. Now, before you start writing your book, the very first question you need to ask is, well, what type of book am I trying to write? And there's a great framework that I love using here. This is a key framework that we teach in our beginner writing program, ship 30 for 30. It's called the 4A framework. And what it means is that the vast majority of nonfiction can be reverse engineered into these four different paths or even these four different voices. You have actionable, analytical, aspirational and anthropological. So the first big decision you need to make before you begin writing, and especially even before you begin outlining is, well, which of these paths am I going to take in my book? Right? So is this going to be an actionable book? Is this going to be an analytical book? Is this going to be an aspirational book or is this going to be an anthropological book? And if you don't know, just quick crash course on each one. Actionable is very how to, here's how to do something. Analytical is like here's why something works or here's why something is happening based on data. Aspirational is I did and you can too. Or if you're curating, you know, all these other people did and so you can too. And then anthropological is more of the underlying psychological reasons why something happens, usually in society or having as it relates to human nature. And so this is the first big decision you have to make. And I find that most people when they sit down to write a book, the very first thing they do is they just open up a word document and they start writing the first sentence. And that's a bit like, you know, the metaphor I like to use is that's a bit like showing up to a forest in the middle of the night with a flashlight going, well, I gotta find my way Home, Right. You don't. That's not a very productive place to start. You want to understand, well, where am I in the forest and where's home? Right. And so the easiest way to answer that question for yourself is to figure out, well, which of these four as am I going to use? After you've made this decision, everything else sort of takes care of itself. But if you don't have this level of clarity going into the writing, what happens is you just write and write and write, and you don't really understand, well, what is the true value that I'm giving the reader. And if you just, you know, pretend, like, pull outside of yourself for a second. If you are a reader and you go into a bookstore as a reader, this is how you make decisions. You ask yourself, am I looking for an actionable book? Am I looking for an analytical book? Am I looking for an aspirational book? Am I looking for an anthropological book? Right. And if those are your expectations when you pick up a book, that's what you're expecting that it's going to give you. So you have to kind of keep that in mind as you consider, well, what sort of book do I want to write? After you make that decision, the next decision you need to make is, how do I want to structure this book? So, you know, I want to write an actionable book. I want to write an aspirational book, an anthropological book, an analytical book. Doesn't matter. So then you ask, well, how do I want to structure this? And I want to introduce you to one of the most powerful writing frameworks that I've come up with. It is a key thing that we teach inside our beginner writing program. Ship 30 for 30. It is something that I use religiously every single time I sit down to write. And I call it the 10 magical ways to expand anything. And the 10 ways are tips, stats, steps, lessons, benefits, reasons, mistakes, examples, questions, and personal stories. And when you understand that all nonfiction can be expanded in one of these 10 ways, you never sit there asking yourself, well, what do I do next? What do I give the reader next? Because you're always just going to be recycling back to one of these 10 magical ways to expand anything. So I'm going to walk you through how you combine the 4A framework with the 10 magical ways to expand anything. A really helpful baseline that I like to use when I'm outlining a book. The average nonfiction book is about 60,000 words. So if you just do some really clean math, that means to write a book, you are going to write 10 chapters that are each 6,000 words long, which is essentially a long form blog post, right? And so if you just think, okay, that is going to be the architecture of my book, right? I've picked one of the four A's. I know which path I'm going to take. And in order to execute and write this book, I am going to write 10 chapters, and each chapter is going to be 6,000 words long. And having that baseline really helps me understand, okay, what do I need to create very actionably, very tactically, what do I need to create in order to end up with a book, just in the most literal sense. So the way I like to start outlining is reminding myself, okay, the average nonfiction book is 60,000 words. That means 10 chapters, roughly 6,000 words per chapter. And so what I do is I open a document, and I just start going chapter by chapter, and I go, chapter one, chapter two, chapter three, chapter four, chapter five, and I just do a bulleted list, chapter six, chapter seven, chapter eight, chapter nine, and then chapter ten, and I just start. We're going to essentially outline an entire book just inside a bulleted list. And this is when you can compress your thinking this way. I promise, it makes the writing that comes later so much easier. Okay, so we have ten bullets, one for each chapter. And then as a reminder to myself, in parentheses, I like to put 6,000 words next to each one, right? Just so I know. All right? That's the goal. And so I do that. And right now, this is a mechanism I like to call prepping the page. So the reason that I'm going through and I'm sort of doing these manual steps is because it helps me feel like I'm making progress. And there's something psychological when you're outlining and writing a book, because, you know, writing a book is a. Is a large undertaking. You want to find little ways to trick your brain into feeling like you're making a ton of progress very quickly. So I always like finding ways to prep the page so that I feel like I'm making a ton of progress really quick, quickly. Okay, so 10 bullets, 10 chapters, 6,000 words each. All right? Then the next decision is you go, okay, I have 10 chapters, and they all need to ladder up to one of the four A's. So let's just pick some topics, right? Topics for books, and I'll show you how this works across a bunch of different topics. So let's say topic one. I've been working on a copywriting book in the background let's say topic number two is yoga and topic number three is wealth management. Okay, I'm show you it doesn't matter what the topic is. In nonfiction, this framework works for everything. Okay. And let's say for copywriting, we want that to be an actionable book. Yoga, we want that to be an aspirational book. And wealth management, we want that to be an analytical book. Okay, so then, and I'll just go through each one by one. Then you need to decide, well, what are the 10 chapters that I need to cover in order to deliver on the promise of here's an actionable copywriting book, or here's an aspirational yoga book, or here's an analytical wealth management book. And the way I like thinking about this high level is that each chapter, think of it as a different pile on your desk and you go, whenever I'm writing about this topic, it goes in chapter one's pile. Whenever I'm writing about this topic, it goes in chapter two's pile. Whenever I'm writing about this topic, it goes in chapter three's pile. So a different way of thinking about chapters is just, what are the big main points that I want to make? What are the large categorical points that I want to deliver on in my book? And every time I'm writing about a certain topic or a certain category, I'm just putting it in a different pile. Okay. And a really easy way, if you're sitting there and you go, I don't know how to do that. Well, let's refer back to the 10 magical ways, right? If you really wanted to, you could use one of the 10 magical ways as the primary bucket for each chapter. So let me show you how this works. So let's say we are. We'll. We'll use the. The copywriting an actionable copywriting book. That's what we want to write. As an example. Well, we could make chapter one tips on how to get started copywriting. We can make chapter two stats on why maybe copywriting is an exciting career path, you know? Chapter three, here are the steps to get started. Chapter four. Here are the lessons that I've learned over the past 10 years being a copywriter. Right. Chapter five, benefits. Here are the benefits of becoming a copywriter and why you should care about it. Right. Chapter six, here are the reasons why everyone should become a copywriter and, or, you know, here are the reasons why people who get into copywriting make X amount of money or whatever the reasons are. Chapter seven, Here are the mistakes most people make when they first get into copywriting. Right? Chapter 8. Here are some examples of successful copywriters or success stories of, you know, creators who got into copywriting and they ended up achieving their dreams, you know? Chapter nine. Here's some questions you should consider asking yourself if you're thinking about getting into copywriting or maybe a little bit more advanced. Here are some questions that you can ask clients to extract the best content from them. Right? And then chapter 10. Here are some personal stories of, you know, just war stories. Here are things that I ran into in my copywriting journey, and here are some interesting takeaways that I had from each of them. Right? 10 magical ways, 10 chapters. Each chapter focuses on a different thing, right? And that high level is a very, very, very easy way of thinking about structuring a nonfiction book, okay? And you're covering, like, all sorts of different ground, all right? However, I would consider this to be the most beginner version. You know, like, if you've never written a book before, this is a really easy place to start because you're just. You're acquiring all of these new skills, and this is an easy framework to go execute. However, all of us here recognize that the vast majority of the nonfiction books that we read don't usually cover all of these different things, right? In reality, most nonfiction books only lean into a couple of these. That's not to say that you. That you can't use them or you can't use all of them, but I'll give you a really easy example. You'll probably recognize it immediately. Every one of Ryan Holiday's books reads the same. Each chapter is a different person's story about whatever the central topic is, you know, so he'll be like, this is stoicism and leadership. And then each chapter is a different noteworthy person's story about them being a leader or becoming a leader. And the first half of the chapter is the retelling of that noteworthy person's story, which is like cure curating a story. And then the second half of the chapter is Ryan's personal commentary on that noteworthy person's story and some of the lessons and takeaways, right? Maybe benefits, maybe mistakes, right? Maybe like, if you were to extract this for yourself, here are some things that. Here are some lessons to take away. Here are the benefits of this. Here are the mistakes that you would avoid, right? And it's. And he just sort of sits in that sweet spot. And that is the majority of all of his books on stoicism, right? So you can pick and choose how you use these. But these 10 magical ways are very, very powerful in expanding any sort of nonfiction content. However, this is only the tip of the iceberg, okay? Because really, what you want. And if you want to use the one magical way per chapter, that's totally fine. But really, the V2 of this and how I would encourage you to think about this is you want to make each chapter a different main point or a different topic that you want to talk about, okay? And starting with the 10 magical ways is usually an easy place to start. So let's use yoga as the next example and say you want to write an aspirational book, right? Well, chapter one. Aspirational. What is aspirational? Aspirational is always some variation of, I started with nothing, I ended up with everything. Or I had everything, I lost it all. And then I rebuilt myself, right? It is always some version of zero to hero. Okay? So chapter one, it might make sense to start with mistakes, right? Mistakes I made as a yogi. Okay, so we're going to start with the negative. We're like, we're all the way down here. And then over the course of each chapter, we're going to progressively go up the hero's journey, right? We started with nothing, or we started with all these mistakes, and then ultimately we ended with something. So maybe just to get the outline right, we're going to put chapter one first, and then we're going to pick what chapter 10 is last. We go back to our 10 magical ways. Maybe it would make sense to end with questions, sort of like ending a. Like a podcast with a Q and A or a talk with a Q and A. It's like, at the very end, here are all the questions people have asked me about my. My yoga journey, right? In fiction, this is called. People use this especially in movies all the time, but this is called First Image and last Image. First image is like, what's the very first scene? What's the first thing that you see when you're watching the movie that gives you the sense of, oh, this is where the story is starting. And then the last image is, well, what's the last image that we see? And how do we know that the story is complete? And you can use a similar framework in nonfiction, where you ask yourself, where are we starting? And where do we want to end up? Right? And then we just fill in the middle. And maybe chapters two through nine are all different stories, right? And so this is where you would if you wanted to write an aspirational book and you wanted to write something about your own life. You would just pick, like, different stories. Like, maybe chapter two is my first yoga class. And then maybe chapter three is like falling. Clever wordplay. Falling in love with hard positions. And then, like, it's a whole story about how you're just falling over and over and over again until finally it clicks and you build strength. Okay, like, aspirational story, right? Maybe I am by no means a yogi. So I am just making this off the top here, and we'll see if it works. Chapter four. Maybe we're like, you know, finding the right studio for you, you know, chapter five, chapter six, right? You're just going through and you're just picking these different topic areas that are related to the thing that you want to write about. Okay? That is sort of, if you think about the highest leverage decision you can make in outlining your book, this is really what it is. You're like, what are my 10 piles? What's all the ground that I want to cover? Then within each pile you go, well, Cole, I have to come up with 6,000 words for each one of these piles. How on earth am I going to do that? I'll tell you exactly how. 10 magical ways to expand anything, right? So let's take chapter two. My first yoga class. Okay, My first yoga class. Let's say we open that with, again, here's some mistakes that I made or even, you know what? No, let's open with personal story, because that's one of the 10 magical ways. Personal story. What happened when you walked into the first yoga class? Then in the next section, maybe what you do is you share some lessons. You go, I just told you the story. Now let me share some lessons with you about what I learned going through that experience, right? And then maybe you give some tips where you go, hey, now, if you're going and trying to, you know, get started doing yoga and find the first yoga class for you, here's some tips that I would give my former self, right? Or I would give you reader, right? And then after I give the tips, here are the reasons why I'm giving you the tips, right? Here's why I am suggesting what I am, right? And usually within that, it's some mistakes, right? The reason why I'm telling you to do it this way is because when I was going through this, I made these mistakes. You know, these are the mistakes that I wish that I didn't make or I want to help you avoid, right? And then maybe after mistakes, you give some examples. You're like, for example, this is what a mistake would look like. Or for example, when you don't make this mistake, here is how your life is different, right? Here's how your life is better. And then maybe just for fun, you throw a stat in there and you're like. And just so you know, the vast majority of people only show up to one yoga class. Like 90% of people take one yoga class, and then they give up. And really, you have to give yourself more time than that. You have to allow yourself to fall in love with the habit, with the practice. Which leads nicely into chapter three, Falling in Love with Hard positions. Right? And so there's the whole chapter. We just, we just outlined the chapter. And then underneath each one of these bullets, what you would do is you would start writing little notes to yourself. So under personal story, you would say, you know, it was 2009 and a frigid day in Chicago. I will never forget seeing this yoga studio open up down the street from me at my day job and wondering if I would ever end up walking in there. I had been thinking about diving into yoga for a while, but to be honest, I was terrified of taking my first class. I was sure I would be horrible at it, right? So you just literally start jotting down notes and you're not critiquing the writing. This is the most important part. All you're doing is you're going underneath each bullet and you're just allowing yourself to brain dump. You're not thinking, oh, is that a beautiful sentence? You're not thinking, oh, is this a really well written paragraph? You're not asking yourself, oh, is this all in the perfect order? All you're doing is you're starting really high level, right? You're illuminating the whole forest and you're just chunking things down into bulleted lists. So again, just to recap, the highest level decision is, which of the four A's are you going to use? Are you going to write an actionable book? Are you going to write an analytical book? Are you going to write an aspirational book or are you going to write an anthropological book? Once you have that decision, you bullet out. Here are my 10 chapters. Each chapter is 6,000 words. Then next to each chapter, bullet, you ask, what pile is this? What main idea am I going to cover here? And then when you come up with the main idea, you use the 10 magical ways and go, and what are all the things that I could share inside of this idea? And you list out from the 10 magical ways, you know, I could probably share some Lessons. I could share some tips, I could share some reasons, I could share some mistakes. And then beneath each one of those bullets, you start just sharing the chicken scratch, right? Personal story. Okay. What personal stories come to mind? Reasons. What reasons come to mind? Tips. Okay. What tips come to mind? And by the end, what you should have is you should have a big bulleted list that essentially has all of these decisions done. And then once you have that, it becomes so much easier to sit down and do the writing. And the very last thing I want to show you is that once you do this, you are basically going to replicate this in the writing itself. So let's. Let's stick with chapter two in our yoga, maybe our yoga memoir here as an example. Okay. Call this yoga memoir. What I like to do when I am finished with my outline is then I will open a new document for each individual chapter, right? So if you want to get super organized about it in Notion or just in a folder on my laptop, I will create 10 different notion docs, or 10 different, you know, word Word doc files. And each chapter, I take that section of my master bulleted list and I copy paste it in there. And so what I'm really doing here is I'm basically going, I'm going to start writing now and I'm going to throw all my notes into it. But you can, you can trick your brain into feeling like you're making more progress than you actually are by continuing to prep the page. So then what I do is I take my chapter title, I put that at the top, and then I go down the list, I go return, return, return. And I go, oh, yeah, the first section that I want, okay, this is going to be a personal story. And then I make that the header, and then I go, return, return, return. The next thing that I want is we're going to talk about lessons. And then I make that the header. And then I go, return, return, return. And then I go, tips. That's the next thing that I want, right? So what you. What you should end up with is something like this. You should end up with a big word document that is truncated by different sections. And then you would go back to your bulleted list and you take the notes that you wrote to yourself, and you just copy paste them inside each section. So at the end it should look, you know, something, you know, say we got like, lesson is don't judge a yoga studio by its cover. Another lesson that we put is like, give it a month. Another lesson is like, make friends, not competitors, whatever. Okay, so you're just like brain dumping. Here are all the different things that I want to talk about. So that way, when you sit down to write, notice how much easier it will be to write this chapter, because I already know these are the sections that I want to cover. This is how much real estate each section is going to take up. And I don't really need to think about writing each section because I have all of the notes in there. I know exactly what I want to say, right? I've already done the thinking. Now I just need to sit there and take my chicken scratch and then just clean it up, right? So maybe we take this. We know we're going to open with a personal story, and we go. The year was 2009. I was living in Chicago at the time, just up north near Wrigley Field, you know, and every day I would commute to work an hour both ways. And then you just continue with the writing. And all you're doing is you're just pulling from your little notes here. And it's so much easier when you sit down to write, to not just start with a blank page, but now you have the direction. You know which direction that you're going to go in. And whenever you get stuck or whenever that inner critic comes out and starts going, oh, that's not a very good sentence, you go, it doesn't matter, right? Because I've done 90% of the heavy lifting. I know that really what matters is that I just cover this topic in this way at this part of the chapter. So let me just go deliver on that. And then at the very end, I can obsess over whether or not that's the right adjective. But this is the majority of the work. And I find that the vast majority of the time, the people who struggle to write books the most are the ones who skip this entire process and they just dive right in and they start writing words linearly. They go, I opened a word doc, and now I'm going to start writing my book. And in my opinion, you know, I've written 10 books at this point. That is the hardest way to write a book. It is significantly easier for you to start by understanding what is all the ground that I want to cover, right? What are all the different points that I want to make? And then after all of those decisions are done and you've prepped the page, you've. You've prepped the outline of the whole thing, you've prepped the page of each individual chapter, you know how many words each chapter needs to be. You know what sections that you're going to cover, you know which stories you're going to tell inside we it which section right after you make all those decisions. The writing takes care of itself. But if you don't take the time to do that, then what ends up happening is you just start writing the first word and then the second word and then the third word and then you're like, I don't like that adjective delete. I go back to the second word. I write a couple more words. I don't like that opening sentence. And it is the most unproductive thing you could possibly do as a writer. So that is why I wanted to introduce you to this overarching framework. This is how I outline every single thing that I create. I very, very rarely sit down and just start writing linearly. I always start with a bulleted list and I always try and organize my thinking just like this before I begin writing.