How To Outline A Non-Fiction Book In 25 Minutes

I have a very specific process for how I outline a new nonfiction book that I want to write. And so like, for example, this is how I outlined and wrote The Art and Business of Ghostwriting. This is how I outlined and wrote Writer Career Paths. And this is how I outlined and wrote The Art and Business of Online Writing. Okay. And I do the same thing over and over and over again, every time I sit down to write a book. And so I thought it would be helpful to walk you through it. So you can do this in any word processor you want. You could do this in Google Docs. You could do this in Obsidian. I've been using Notion a lot lately, so I like doing it in Notion. Ultimately, it doesn't matter. We're just talking about individual pages. Okay, so the first thing I do inside of Notion is I create a master page. Think of this as the hub for all of the individual files of your book. Okay, so here we call this the book hub. And let's say I want to write a book called, I don't know, Copywriting 101. Okay, so I want to write a book about copywriting. Okay, so the first thing that I do is I create inside of this hub, I create a new page, and in this page I will make this my book outline. And so here would be, you know, Copywriting 101. Okay, great. Now, I— the way that I approach outlining is, like I said, the same every time. And when I say the same, what's really happening is most nonfiction books, you know, I've written 10 nonfiction books, I've written thousands and thousands of newsletters and articles on the internet. I have written so much nonfiction over the past 10 years that I've really realized that the vast majority of nonfiction, unless you're writing something a little on the margins like a Malcolm Gladwell style book or, or like a Ryan Holiday style book, right, may, maybe more story-driven, most nonfiction is centered around actionable advice, how to do something, okay? And when you think about that, uh, that means that most nonfiction follows roughly the same logic line, Okay? And once I point this out, you will probably recognize this. You'll go, oh yeah, most nonfiction books that I read all follow the same logic line. Okay? And so the logic line goes like this, and, and this is really, when I say logic line, these are the things that you need to walk readers through in order to get them from where they are, right? They haven't read your book yet. So in some way they have a knowledge deficit and then where you want them to end up. They've read your book. Now they have new knowledge. Right? And so this logic line is really all the individual steps that need to happen along the way to move them from where they are to where you want them to be and ultimately learn something. Okay? And so I noticed that I use the same logic line over and over and over again, and this is what creates the outline for the book as a whole. All right? So here we have our introduction, and the introduction is almost always the origin story. Now, the origin story is really the, I, I am just like you. I have, I had these problems that you probably have right now. You know, these negative things were going on in my life. I'm sure you can relate. And then all of a sudden, one day after I had tried all these things that didn't work, one day there was a catalyst. Something changed for me. And as soon as I started taking this different approach, all these good things started happening until fast forward, here's where I am today. Look at all the things I've achieved. And now you reading this book, I am so excited to pass along all my learnings to you. What I've just articulated is basically every introduction to every actionable nonfiction book ever written. Okay, so your introduction is really just going through this mini logic line. Okay, and so again, if we summarize it here, it's like, I was just like you, negative things happening in my life. I tried everything until one day, some sort of catalyst, benefits of new or different thing. Fast forward. Here's where I am today. Look at all I've accomplished. This could be in any domain, right? And then ultimately, I did, and so can you. These are basically the mini beats that you would hit inside of an introduction. So we know this is how we're going to start the book, right? Then we start getting into the chapters. So we know we're going to have Chapter 1 and Chapter 2 and Chapter 3, etc., right? When I sit down to write a nonfiction book, just to level set, right, if the average nonfiction book is like 60,000 to 80,000 words and you have approximately 10 chapters, right, then you might say, all right, that's roughly 8,000 words per chapter, something like that, right? So you sort of have that as a barometer. That's usually where I start. Um, you might end up with 12 chapters and fewer words per chapter a little bit. You know, you might have 15 chapters and even fewer words per chapter, or you might have 5 really long chapters. It doesn't matter. It's just you have these 2 levers, right? There's number of chapters, and then there's word count per chapter. And the goal is you want to land somewhere in the 60,000 to 80,000 words end count, right? So here, each chapter, if you think about— and notice how, like, we're not even getting into the writing. This is just purely the high-level construction. Each chapter individually is representing a different grouping of ideas. So this is where we go back to this idea of following a logic line. All right, and in Chapter 1, the first thing we need to tell the reader is, here are the reasons why you should do this new and different thing that I'm proposing to you. Because I could give you the solution, but you're not going to do it if you don't understand the reasons why it's important or why it's different. So first, I have to explain to you, here are the reasons why I am encouraging you to do this new and different thing, right? The second bullet on the logic line is, and here are the mistakes to avoid. This is valuable and this is important because once you tell someone, here's why you should do something, you also need to tell them, hey, and before you get started, watch out for these potholes. I have your best interests at heart, right? Which leads to the third bullet point, of, okay, I told you why you need to go in this new and different direction, and I told you what mistakes to look out for. Now I need to get you excited about the adventure. Here are the benefits. Here are all the good things that are going to happen if you go in this new and different direction, right? I got— you got to motivate the person. I got to dangle the carrot at the end going, hey, there's a pot of gold. All right, don't worry. This is really the setup. So your introduction, chapter 1, 2, and 3 is really setting you up for all the rest of the book. Because the origin story is what connects the reader emotionally, and then the reasons why is what gets them to understand, okay, this is not like all the other advice that I've gotten on this topic. Mistakes to avoid helps deepen that trust. Hey, I have your best interests at heart. I'm going to make sure that you don't make these mistakes like everyone else does, and then I get you excited. Here are the benefits, right? Which then leads into what I like to call the meat of the book. This is really what people are buying when, when someone goes and buys a $20 or $30 book, what they are really buying is the middle. Okay. The meat, because this is where you start giving them something actionable. So here, Chapter 4 and Chapter 5 and Chapter 6 and Chapter 7, these, these can all be different subtopics, but these are all different how-to chapters. Okay. So using our example here, like if we're talking about Copywriting 101, all right, Chapter 4 might be how to write really great copy, and then Chapter 5 might be how to find clients who need copywriters, and then Chapter 6 is how to write really great subject lines and landing pages and video sales letter scripts, right? And then Chapter 7 is how to package and price your services. So these are the different actionable things that you're gonna pass along to the reader, and again, we can't really just jump right into the how-to. We need to first set up the experience for the reader, right? We need them to trust us. We need them to empathize with us. We need them to understand why we are encouraging them down this new and different direction. They need to know all these things before they can go, okay, I trust you. I take your advice. Now tell me what to do, right? And so you could have, in theory, I mean, you could have 4 how-to chapters, you could have 8 how-to chapters. It doesn't really matter, right? Just remember your 2 levers, number of chapters and word count per chapter. Then you have kind of two closing out chapters. Chapter 8 is usually, and I'll just frame it as something easy like tips. And what I mean by tips is more like insider tips, okay? Because you got the reader excited about this new and different direction and you just told them how to do lots of things. But I'm sure there's probably other little golden nuggets that you picked up along the way that would be worth passing along to the reader. The reason I say insider is because oftentimes we take for granted the knowledge that we have. We take for granted all the things that we've learned on our journey. And this is a great chapter to sort of be like, hey, I know I just told you how to do all these things. Little pro tips. Here are the little things that you should know to maximize your success. It's a great, great chapter to end on. And then lastly is questions, because even though you explained all these things to the reader, do you think that they have no questions? Do you think they're going to hear it once and just execute it perfectly? Of course not. They're going to need some help. And something that took me about a decade to realize, and this fundamentally changed how I now think about and write a questions-style chapter— just think of it like an FAQ— is that most questions are actually objections dressed up as questions. So one that I see literally every single day in our different writing programs is I'll explain something and then the person will go, yeah, but Cole, will this work for my niche? Will this work for my industry? That's not actually a question. That is an objection phrased as a question. The objection is I don't think this will work for my niche. I don't think this will work for my industry. And so this is actually a really important part of writing a great book, a great nonfiction book, is after you explain all this stuff to the reader, you want to proactively address their questions, aka their objections. All right? Because, and this has been a lesson for me mentoring, you know, north of 15,000 writers across our different writing programs, is that most of the time teaching people hard skills is not the challenge. A lot of hard skills can be picked up pretty quickly. You do it 3 times and you kind of get it. The challenge, and where everybody fails, is on the soft skill side, where they get in their own way, or they know what to do, but they have that voice in their head asking questions, aka stating objections, telling them why it won't work for them or why they can't, right? So I always like ending books when possible, and you can do this throughout the book too, but I like thinking about how do I address all of those questions or objections at the very end. Okay. So here, this is really the high-level outline. And if I was going to fill this in, I'm not going to take the time to do it now. But if I was to fill this in, what I would do is I would take my topic, Copywriting 101, and I would start fleshing out each of these sections inside of my bulleted list. So just to show you what this would look like, I know that in Chapter 1, I'm going to talk about the reasons why. So I'm going to start doing a sub-bulleted list going reason number 1, reason number 2, reason number 3, reason number 4. Reason number 5. Right now, why is this helpful? Well, the reason I want to do this in my outline is because, A, this is the highest leverage, highest value decision I can make in the writing. Right? Like, I actually don't need to write this whole chapter in order to understand what I'm trying to share with the reader. The chapter is Reasons Why, and I should take some time to hammer out the 5 reasons. Right? So this is a very strategic decision. And then second is depending on the number of reasons, I typically say per chapter you want to think of 3 to 10 things that you're giving the reader. Okay. So reasons, you might give them 5 reasons. Mistakes, you might give them 4 mistakes. Benefits, you might give them 7 benefits, right? You typically, you don't want less than 3 because it sort of makes the reader feel like they're getting gypped. More than 10, you better have a good reason for it, but more than 10, it probably is overkill. All right. So the sweet spot is 3 to 10. And so I know that if I take the time to do this in my intro, what I'm also doing in this bulleted list is I am creating the outline for each individual chapter, and I'm going to show you what, what this looks like here in a second. So this is what I do for every book that I write, high level. I basically use the same logic line, and then I go through and I identify, all right, so what actually are the big ideas that I want to share? And the big ideas are grouped by chapter, and then the individual— think of these as the main points. These are the main The main things I want to share in Chapter 1. These are the main things I want to share in Chapter 2. Okay. And this is what creates the outline. Now I'm going to take this. We're going to use Chapter 1 as a little example here, and we go back to our BookHub. All right. So let's pretend the outline's done. And I would really encourage you to flush out that bulleted list as much as you possibly can, like get as many main points out as possible, expand them, chicken scratch, just ramble, whatever comes to mind. But as long as you're, you're operating inside that bulleted list, you have a really tight container. Okay, so even if you're sort of rambling inside of, you know, it's a reasons chapter and reason number 3 and you just ramble and go down a random rabbit hole, that's fine because what you're really doing is you're getting all those ideas out inside of that tiny section and then I'm gonna show you how that influences the writing thereafter. So here, if we go back to the BookHub, we have our book outline, great. The next thing to do is to create individual chapters for, or individual pages for each chapter. So here I would have Copywriting 101, let's say that's the name of the book, and I would have chapter 1 And then I would have reasons why, right? Now going back here to the, to the book outline or the Book Hub, notice how by having this for all 9 chapters, for example, now I have individual containers for each chapter, right? So if I just to show you what this looks like, Copywriting 101, chapter 2, mistakes. And then we go back and then we go Copywriting 101. Chapter 3: Benefits. Pretty simple, right? So I'm just going to do those just to show you. All of a sudden now it starts to feel like your book's coming to life. Now, the benefit of this, and I want to be really transparent about this, there are two big benefits of doing this. One is it creates very clear containers so that as you get into the writing, you don't feel like you're tackling this giant book. You now, you've broken it apart into 9 sections or 10 sections, right? By isolating each chapter in its own page, it just immediately makes it feel more actionable. And second, you have to remember that the hardest part of writing a book is managing your own monkey brain, okay? It's not that writing a book is hard. I mean, yeah, there are new skills and there are things you have to learn, but like, ultimately, especially if it's a topic that you have proficiency with, you probably know a lot of the things that you want to say. It's kind of just a matter of sitting there and saying it for hours, right? And so part of writing a book and things that I have found help me a lot is you want to find ways to trick your brain into feeling like you're making giant leaps of progress because it makes you feel like, oh, I didn't just start writing my— I'm not at the 1-yard line. I just jumped. I'm like 20% done. And one of the ways that I have found to do that and accomplish that is to shell out the book like this, where I have my outline and then I have individual pages for each chapter. Instantly makes me feel like the book is 20% done. And so I get this feeling of gratification. I get this feeling like, oh, I've already invested so much in this book, even though I can do all of this in literally like 10 minutes, right? So you want to find these little ways to trick your brain into feeling like you're making these giant leaps of progress, because that's what's going to allow you to stick with it. All right. So then remember our outline, we did all the thinking here, right? So then inside of each chapter, before I even start writing, What I do is I take that section of the outline and I just copy paste it over. I copy paste it into the doc. Now, if I was to expand this out, this would be much larger, right? I would have all 5 reasons listed out and then next to all 5 reasons, I would have chicken scratch of what are the things that I want to say to expand on that? Is there a story I want to tell? Are there other mistakes I want to point out? Are there little tips I want to give the reader? Um, are there like literally anything I want to share related to all of the 5 reasons? I just chicken scratch it out. This goes back to— this was a technique that I developed during my ghostwriting days, because what I would do when I was ghostwriting for founders and executives is I would get on a call with them and I would record the call. And then after the call, I would take the transcript of the call. And when I would go to turn the transcript into an article or a newsletter or something like that, what I would do is I would put up two windows on my computer. And on one side, I would have the transcript, and on the other side, I would have a blank Word document. And the very first thing that I did whenever I was trying to work from a transcript is I would read through the transcript or skim it, and I would try to identify, okay, what's the big idea here? Like, if we're gonna write an article based on this call, this recorded call, what's the article about? And I'm trying to look for information or things that the client shared on that call in the transcript that would be useful in writing that article. So I'm skimming the transcript, and every time I find something like, oh, that little story they told, that, that is something that I could use, I would highlight the story from the transcript and I would copy paste it over into the fresh document. And then they'd maybe rattle off like 3 tips at different points in the call. So I would find those and I would copy paste them and I would put them into the fresh document. And the reason I would do this is because basically I would try to take an entire transcript and then only extract the individual pieces that I needed. And then once I had the chicken scratch pieces, then I could sit down and write and I kind of already knew what I wanted to say because the client already said it. They just didn't say it in clean prose. So the way I liked thinking about ghostwriting was I wasn't really writing. I was more like identifying and whittling down information and then just cleaning it up. And that technique has ended up being very helpful in my own writing, where when I outline now, what I do is I try and fill in the outline with as many pieces as possible. And then I copy-paste all those notes into each individual chapter page, right? Because what I want when I sit down to write is I don't want to write staring at a blank page. What I want is I want to start writing by looking at the first version of all the ideas that I wrote, right? Now, the last step here, and we can push this one notch further, and again, what you would do is you would, you know, go inside your outline and you would copy-paste, you know, the mistakes into the mistakes chapter and the benefits into the benefits chapter, right? So you're throwing the chicken scratch in each individual container. Then once you have the chicken scratch, I like to push it one more notch and go, now let's prep the page for each chapter. So what this means is when I start writing, I do not want to have a blank document and I just have to start writing from the very top to the very end. Okay. It's the metaphor I like using is it's a little bit like being dropped in a forest. And it's pitch black out and someone goes, here's a flashlight, find your way home. You can only see like 2 feet in front of you, right? It's going to be very hard for you to identify where you're going and where the exit is from the forest. It would be much easier if you could take a 30,000 view or 30,000-foot view and be able to see the whole forest all lit up and then go, oh, I see the exit is that way. I need to walk in that direction, right? When you prep the page of each individual chapter, that's basically what you're doing. You're getting out of the weeds. All right. You're not trying to navigate the forest with a flashlight. And instead, what you're doing is you're pulling up 30,000 feet and you're able to see the chapter as a whole. You're able to see it not as individual words, but as sections stacked on top of each other. And here's what's so cool is if you take the time to outline it this way, the outline literally makes all of those decisions for you. You already made these decisions. All you have to do is format it. Okay, so we know if this is the, the outline, like we're going to share 5 reasons in Chapter 1, how do— what do we think prepping the page is going to look like? Well, we're going to have our introduction up here, and then our first heading is going to be Reason Number 1, and then we go down a bunch, and then we're gonna have Reason Number 2. And then we go down a bunch, we're gonna have reason number 3, and then we go down a bunch, we're gonna have reason number 4, and then we go down a bunch, we have reason number 5. And now I can see the whole chapter. I go, oh, it's, it's not actually one big document, it's 5 or 6 individual sections. This might, this might seem like a really small and inconsequential tactic, and I promise it's not. Just by doing this, it makes you feel like the chapter is already half written. Okay? And what makes you feel like you've made even more progress is if you go back to your bulleted list, like again, imagine that I filled all this out and it's like, reason number 1, you should start doing XYZ. Here's a little story. Like I expand out each reason. Then you would go into this outline again and you copy paste everything that you've come up with for reason 1 and you put it there inside the section. And now when you begin to write, you can see your chicken scratch. So you're not actually writing from a blank page. What you're doing is you're writing here, but you're looking at all the things that you, you've already identified you want to say. And then the process of writing a book is not— I think where so many people struggle is they don't do any of this prep and they just open a blank Word document and, you know, try to write a book. And you don't realize that when you do that, you're basically trying to figure out how to organize and structure the book while you're also focused on writing great sentences and paragraphs and writing a good book, which is like being hyper in the weeds and thinking high-level strategic at the same exact time. It's very difficult. It's, it's much easier to only focus on one at a time. You start high-level strategic, you make all the high-level decisions, you organize everything, you create separate containers, you break each container apart into pieces, you fill each container with chicken scratch, and then all you have to do when you move into phase 2 is you just fill in each section. You've already made the decisions of what you want to say. You're just filling it in. You're just turning chicken scratch into real prose. Okay. I cannot emphasize enough how much when this process clicked for me, and this is how I approach writing all nonfiction books now. My first nonfiction book took me 4 years to write. My second nonfiction book took me less than 4 months to write. And my third nonfiction book, I I, if I remember correctly, I literally think I wrote the whole thing in like 2 weeks. And now I could, I can do this. I could write an entire nonfiction book in 5 days, like easily. And the reason is, I mean, yeah, I've become more proficient as a writer over the years, but the reason is that I've improved my mental model. I've improved my approach. I've found ways to consolidate actions and decisions. And chunk them together and go, I want to make this grouping of decisions here first, and then I make this grouping of decisions second, and then I make this grouping of decisions third. Right. The reason my first book took so long was because I didn't have that mental model. And so I was basically trying to figure all of the pieces out at the same time while writing. It's too challenging. So anyway, I just thought this would be helpful to push this one step further. If you do this inside Notion, um, I'm also engineering a really cool Claude skill where basically you can connect Claude Cowork to Notion and then execute all of like this whole process and all of my writing frameworks and everything, and it'll just one-shot an entire nonfiction book for you. Now, obviously, um, there are things that you'll probably want to tweak and change. You might want to change the formatting of certain things. You might want to change certain examples. The personal story element is always the hardest one. right? Because, because AI can write very, um, straightforward thought leadership style, tactical, strategic type content. But what it doesn't have is a ton of context on your personal stories or examples. So those are things where you either insert them after the fact or going into the writing, you can do a huge brain dump of like, here are all the stories that I want to include in my book, et cetera. And then AI can help pull, pull from them. So anyway, just thought this would be helpful. And, uh, if you have any questions, let me know.