072: How to Start Writing a Book, Course, or Workshop
8 Dec 2025 · 19 min
Jenny Blake teaches how to structure a creative project by starting with the transformation you want to create. Define what people should know, feel, and do, then organize your material into three main pillars with repeatable ingredients like quotes, stories, and data.
Chapters
Every holiday shopper's got a list. But Ross shoppers? You've got a mission like a gift run that turns into a disco, snow globe, throw pillows and PJs for the whole family. Dog included. At Ross Holiday magic isn't about spending more, it's about giving more for less. Ross, work your magic.
This non linear expansive process of working backward from the big idea and the transformation. This will allow you to feel that you're getting started. To go from abstract idea to to more and more structure. To the point where the little units to work on, the little boxes to check within the structure, you'll feel that you can tackle them, that they're bite sized enough that they're less intimidating. It doesn't always make the entire project less intimidating, but I hope that this gives you some strong ideas for where and how to start.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the FreeTime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and.
Team to do your best work.
Now onto today's show.
One of the most common questions that people submit as a challenge when they enroll in the Free Author Toolkit is where do I start? How do I begin? So in this episode I'm going to break down my process of how I go from big amorphous idea to getting started because that can be such an intimidating moment in the process. Going from 0 to 1. Before I do that, let me just point out how helpful it is to ask this question on anything that you're creating or that you have a registration page for. In chapter 13 of FreeTime, I talk about my principle of always be listening. So when anyone signs up for the Free Author Toolkit, which you can get access to as well, at itsfreetime.com authors I ask two questions. If I could wave a magic wand and fix anything in your business, what would it be? And what is your biggest question or challenge when it comes to writing a book? By doing that, I get to know you all a little bit better. Anybody who's interested in the Author Toolkit at the same time as submitting to get free access, there's a little exchange of information. And that little first exchange of information is so helpful for creating the content that's going to follow. Whether I'm building out the Author toolkit, whether I'm creating a podcast episode like this one or I'm writing a newsletter. Perfect. Case in point. As I was trying to think about what could I podcast about today, I thought, aha, let me go to one of my handy spreadsheets that collects registration info and I'll go see if any one question jumps out among the rest. Sure enough, over 50% of you, I would say, who have checked out the author toolkit wrote some variation of where do I start? How do I begin? The first thing that you need to start with is your big idea. You don't even have to have the exact name of that big idea or the title of your book. That often comes much later. And by the way, this all applies to creating a course or a single session workshop as well. I like to follow my friend Alexander Franzen's framework no field do and I tack on a fourth category refer to. So the very first step is within the big umbrella of your idea. What is your intention for this project? By the time people are done experiencing this content, what do you want them to know? What do you want them to do and how do you want them to feel?
Refer to as what are all the resources or most influential materials that you want to be sure to share with them? I would almost work backwards with these questions. First ask how do you want your readers or participants to feel? What is the transformation? I think the biggest number one overarching question of creating anything at all is what transformation are you hoping to create? Transformation means that you are taking somebody from point A to point B, from confusion to clarity, from anxious to excited and inspired. Whatever the transformation you are trying to create, get that down again. Even if you don't have the exact name for the finalized for your project, whether it's a book, a course, a workshop, a podcast, what is the transformation you are hoping to inspire and at a high level for the entire project? What do they need to know and do differently in order for that transformation to occur? Nancy Duarte, in her book Resonate, talks about the storyline that there's usually a gap and right at the start of an effective speech we're painting the picture of the way things are and then the way things could be. Then through the speech we have supporting evidence or pillars, usually about three before we conclude and we restate that vision of how things can be, what's possible. So the same thing applies to you. What transformation are you creating? What is the experience that the person has now? And then paint the picture. What is the vision? Where are you going to take them with your experience?
Even if I were writing something as complex as a book, I would start with a grid written by hand. I find it so much easier to write by hand. I would either do a grid or a mind map of this exact question. Let's say it's a mind map. My topic's in the middle. And then I draw a bubble for no, I draw a bubble for feel. I draw a bubble for do and a bubble for refer to and then go to town. Everything you want them to know in order for this to occur, and so on. I've already walked you through those big pillars. Then I would get a second piece of paper and I would ask, what are the three main parts of the process or parts of the journey or milestones? So within the overarching transformation, what are the modules that are going to be the scaffolding for this big idea? Sometimes, let's say if you're teaching a course, maybe there's 10 modules in the course. So it's not always going to fall neatly into three parts, but you could start with three parts. There is some magic to the number three. I've shared it here before. Our brain works in threes. McKinsey teaches its consultants to pitch problems and ideas in threes. Like to pitch their rationale for something by using three supporting facts or pieces of evidence. It's all over the place. What I like about three is that there's before, during and after. Let's say I was going to teach a podcasting course. I could have a module on before or at least a part on before getting set up during best practices for during an interview or while running your podcast. And after, in the book free time, there's three. Align, design, assign. Interestingly, in Pivot there were four parts, sometimes five, depending how you count it. Plant, scan, pilot, launch is the fourth stage. And then lead was this add on at the end of how to apply it within companies and as managers and coaches. But I will tell you, the first three are the most crucial to the pivot method. Plant, scan, pilot, over and over until you get traction, until you get momentum. And I found that because I was referring to those first three so much, that launch was almost this afterthought tacked on at the end. I realized when working on free time that I really wanted to find three core pillars that would hold the book up. Once you have those pillars, those three parts, now you ask again, what do I want people to know, feel or do to achieve success for each part? So you do the know, feel, do, process again times three for the three main Parts, that is what is going to allow you to understand what the subchapters or sub modules need to be. For example, in the free time framework, the second stage, design. Well, what does it look like to design effectively? What does that mean? What do I need people to know, feel and do? Well, I want them to feel clear and feel that there's purpose and direction and that it's resonating and aligned with their intended audience. So the design stage has sure enough, three parts. You are designing your ideal impact of the project, your ideal outcomes, what you will see produced with you and the team. And then you're also designing process. So impact outcomes and process in order to then write those parts of the book. I'm going to do no feel due again because within each of those three sections I have multiple chapters. Yes, three chapters. I know I couldn't resist. I really went bonkers with free time and these rules of three. Yours doesn't have to be so meticulous. Set of interlocking Russian dolls in pairs of three. But what I do want you to apply is that at every step, whether it's the big idea at the top of the pyramid, the three supporting pillars, or even if you have five modules or five chapters within each main pillar, that for every single one, in order to tackle how you're going to write it or how you're going to teach it, you're going to ask that again. No feel due. And this process is going to help ensure that you create something that is well structured and to achieve the transformation among your audience that you are looking to achieve.
We'll be right back just after this.
When the holidays start to feel a bit repetitive. Reach for a Sprite Winter Spiced Cranberry and put your twist on tradition. A bold cranberry and winter spice flavor Fusion Sprite Winter Spiced Cranberry is a refreshing way to shake the things up this sipping season and only for a limited time.
Sprite.
Obey your thirst with Venmo Stash. A taco on one hand and ordering a ride in the other means you're stacking cash back with Venmo Stash. Get up to 5% cash back when you pick a bundle of your favorite brands. Earn more cash when you do more with Stash. Venmo Stash terms exclusions apply. Max $100 cash back per month. See terms of Venmo me stashterms.
I see a lot of writing advice that tells people to start with an outline and that's well and good. But how do you outline you still need to know where you're taking people, how you want them to feel, and kind of what your North Star for the project is. Maybe you remember from English class in high school or college how to write an essay or how to write an op ed that. Let's say with an op Ed you have your argument and then you have your supporting sections and then your closing. You might have also heard the speechwriting advice. Tell people what you're gonna tell them. Tell them and tell people what you just told them. Yes, it's true. You do need to kind of reinforce things a little bit. That's a different part of the outline that assumes that you know what you're trying to tell people. And I think in order to determine what you're trying to tell people or what supports you need to have in each section of a course or a book, you gotta know what type of transformation you're trying to achieve. And then you need to know how to achieve the sub segments of that transformation. Let's say we're writing a book on wellness and we think that the three main pillars of wellness are mind, body, spirit. Okay, great. Well, what does it look like to be healthy in our mind? What is the transformation? What's the current state and what's the promised land of mind? What's the current state and promised land of body? Maybe it's burnout, too balanced, you know, and then spirit, what's the current state that a lot of people are struggling with? Malaise, you know, depression, foreboding, living in the apocalypse times. And then what's the promised land? Okay, so now within the book on wellness, we have mind, body, spirit, and then what is your unique special sauce that you are going to bring? How do you achieve? So maybe in the mind section, it's meditation, inspirational reading, and connection. I don't know, I'm just making this up as we go along. But you figure out then what are the little scaffoldings that need to stand up each pillar and sub pillar? If you have the author toolkit or you've checked out the your book and big idea workshop, then you know that I like to throw a lot of little ingredients, almost like a chopped salad, into every chapter. So let's say the lowest or smallest unit of what we're creating is the chapter or the lesson. So within the big idea, the book or the course, you have parts or modules and then you have lessons or chapters. Okay, well, to make a yummy chapter or a yummy lesson, it's very helpful to speak to people in ways that they can understand. And every learner or every reader is different.
Over time. I realized that some of these ingredients were really fun. And so with free time, I made a point in my essay tracker, this thing I created in notion that you can see in the author toolkit, I actually made myself go through and ask for every single chapter, what is a good quote? What would be a two sentence summary, a metaphor, a meme, or something viral on the Internet? Is there a graphic to explain this concept or these ideas? What about brass tacks, business advice, things that I have figured out, bulleted lists, numbered lists, you know, really something meaty and brass tacks. What statistics or research might I want to cite? What calls to action do I want to inspire or suggest that people do? And what stories do I want to tell? Both stories from other people and also anecdotes from my own experience. Just to be clear for myself, I call them two different things. So I call them like a JB anecdote or an external story. And then I even sometimes pull in experts as a third different type of person or story or commentary. So going through and asking for what you're trying to illustrate in that chapter or in that lesson of the course, do you have a metaphor? Is there a meme? Is there data? Are there stories? Are there brass tacks, advice and consolidated wisdom? Not that everything has to have all of these, but what are the ingredients that are gonna make your chopped salad? See what I did there? There's a metaphor for every single chapter. Really illustrative and really easy to consume and understand.
Everything I've just described can be done before you ever sit there staring at a blank screen with a cursor and feeling like you don't know where to start. Everything I described, I started with pen and paper. I put the parts and the different subparts and chapters on index cards and I moved them around my dining room table. And I did that more than once, I think, for free time. I had three different sets of index cards because the original structure for the book was mind, time and team. But then I realized that the phrases mind, time and team, they're nouns, they're not verbs, they're not implying or encouraging transformation. So yes, while a lot of the chapters could fall under mind, time and team, I didn't feel that that provided a cohesive, transformative narrative. So that eventually became align, design, assign. And yes, align does happen kind of in your mind, mind, body, spirit. Design does happen about designing your time and how you're going to tackle things and then team. Yes, that is parallel to the assigned section. But once I created verbs around these, I also knew what was missing. I knew that in order to design, it's not just about time. Designing is also about process. Design is about outcomes. There's a lot to design before you ever get to the team part or assigning. So you'll see how this happens. That you start with these chunks of clay or again, index cards on a dining room table. It's got to be tactile. You need to almost move them around in a nonlinear way and see them visually and sit with them, take pictures on your phone, flick through them. When you have some downtime, this is how it all starts to come together. And then I even needed to create board views in notion, not some long document. At no point in the early stages did I just have a long document that's called book draft. I was writing little essays in notion cards that I could move across the board and put them anywhere. And then only later, when I needed to show the book to the developmental editor, only then did I compile things and pull them together. So another thing to realize, especially for those of you working on a book, is that you don't have to write in this intimidating, linear, long, streaming way. Any given chapter is just a small series of essays. A sidebar is a short essay sharing these stories and statistics and metaphors and memes. You'd be surprised. Once you have all of those in your pocket, they're so much easier to just describe one by one, and before you know it, you have a short chapter. It's already there. Then it's so much easier too, for people to bounce off of it and tell you what's missing. Oh, I'd really like a story here. Or this is confusing. Can you flesh this out? So what I've just described this nonlinear, expansive process of working backward from the big idea and the transformation. This will allow you to feel that you're getting started, to go from abstract idea to more and more structure, to the point where the little units to work on, the little boxes to check within the structure, you'll feel that you can tackle them, that they're bite sized enough that they're less intimidating. It doesn't always make the entire project less intimidating, but I hope that this gives you some strong ideas for where and how to start again. I encourage you. If you're really in the thick of things, check out the author toolkit. You can see loom video walkthroughs of how I set up my notion at every stage of the idea, organizing, writing, and revising process. Go to itsfreetime.comauthors for an extra dose of encouragement. Be sure to also check out the book how to Begin by my longtime friendor Michael Bungay Stanier. The book is called how to Start Something that Matters and he walks you through capturing and tackling a worthy goal. That a worthy goal is something thrilling, important and daunting. I'll put the link to that in the show notes and you can also go to MBS Works. Thank you so much for being here. Listening everybody. Happy writing, creating and teaching.
If you've listened this far, you get a gold star.
Thank you.
Word of mouth is the most joyful way we can grow this show and it helps us land interviews with the luminaries and insightful guests that you would most love to hear from. Please send this episode to a friend who might find it helpful and for show notes and related links from this episode, visit itsfreetime.com while you're there, make sure you're subscribed to the Time well Spent newsletter. You'll get instant access to my Tech Toolkit, a continually updated list of all the software I use, along with with the total monthly spend. To run my business where no one works full time Even me, visit itsfreetime.com join Remember, you are running the show. It's time for radical reimagining and everything is up for grabs. Let it be easy, let it be fun, and build with love.
This episode is brought to you by Marketa. When it comes to your payments provider, you can't afford to compromise. Marketa's modern payment solutions flex with your business without the trade offs. Stable and agile, secure and innovative, scalable and configurable. If they say you can't have it all, don't believe them. Your business demands more. Choose a payments provider that delivers more. Choose Marketa. Visit Marketa.com Spotify to learn more.
More from Jenny
215: Stay Relevant, Sense What's Next, and Solve Difficult Problems with Stephen Shapiro
12: Belly of the Pivot Beast: On Bouncing Back from Zero with Adam Chaloeicheep
218: We've Gone Over-Bored (Part 2) with Michael Karsouny (Listen at Your Own Risk!)