Writing a book part 4: Astronavigators
“Now, in general, Stick to the boat, is your true motto in whaling; but cases will sometimes happen when Leap from the boat, is still better.”
—Herman Melville, Moby-Dick
Hey, everyone! This is the last edition in the book prep series—all the stuff that happens before you sit down and start typing up your damn book! Below, we’ll cover the most important things to know about outlining your book, and then you’ll set up a writing plan. I hope this series has been helpful, and I’d love to hear what progress you’ve made and breakthroughs you’ve had in the comments or over email at rachel@racheljepsen.com. Let’s finish up!
Btw you’ll make better sense of the material below if you’ve gone through the other exercises first. In writing a book 2/ you answer a bunch of questions about the guiding force of your book, its purpose, the question it’s answering, the promise it’s making, and more stuff to help to realize the structure of your book. In writing a book 3/ you get to the most basic structural element, or what ‘kind’ of book it is.
An outline is a constellation
Lots of writers come to me with hang-ups about outlines. They can seem like a beast, and something that can be done right or wrong and bad or well. Does it need Roman numerals? How can I be so sure about where it’ll go if I haven’t started researching yet? Can you help me figure out where this story goes? What if I don’t know how it opens? Who’s Roman?
Hey, chill out! Don’t be so intimidated by the prospect of outlining your book, it’s something you get to do to help your writing process later on. Writers outline differently and use outlines differently, depending on the nature and needs of your specific book, as well as your modus vivendi.
I’m working with a few writers who are currently outlining their books, I’ll tell you about two of them. One outlined the first 3/4 of her book within a couple of sessions. She knew the mood, the question it was answering, and the driving force. She knew all about her reader’s pain points and the baggage they might bring to the material in the book. And when it came to figuring out the structure and form that would best answer the book’s promise, she had one idea that ended up a false start before the major structural element (the keel) came out in a single hour-long conversation. Now, she’s working on the book’s constellation—the major and minor points she wants to make, overlaying the keel.
(I guess I could call the outline the skeleton of the ship that’s built around the keel, but I prefer constellation, because it’s more like a painting, a representation that moves, so I’m sticking to it!)
One of the reasons this writer has been so successful at her outline so quickly is because she’s telling a story that she has lived, and the lessons she’s sharing are many of the things she teaches professionally (and because we went through all the steps in this series, of course). She’s writing through ideas she’s been thinking about a long time, and can quickly identify the things she knows and needs to know.
Another writer also lived the story he’s telling, has expertise in his subject matter, but has had a longer, more arduous process building an outline. While our first writer’s outline is a straightforward I, ii, iii structure in a google doc, this guy’s outline is a multi-page excel spreadsheet. It involves multiple intertwining stories, timelines, and perspectives. He also has missing material, like research he needs to do and artifacts to gather, all of which we wanted represented in the outline (so that he could build a writing plan in phases, I’ll explain toward the end). It’s really ambitious (and the book is going to be amazing), and that meant he had to nail this level of detail before he started writing. Otherwise, he would have spent a lot of time writing into different experimental structures, and might never have stumbled into the overall vision he wanted. The form, in this case, carries the purpose of the book; the structure reflects meaning, it conveys something, so the time to get it right was the time that it had to take.
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My point is that the outlining process looks different depending on the book you’re writing, and also on your own practice, how you work. Some writers want to make their outline as detailed as possible, scene by scene and point by point and evidence by example, chapter and verse. Others will lay down the big plot points, or the subjects to be covered, in rough order and get started writing in the gaps, because they’d prefer to discover along the way, or because they have to discover along the way.
An outline is a constellation because you want to represent the whole picture, using as many stars—items you include in the outline—as you need for that picture to come alive for you. That might mean you have five stars, but they’re really bright and the picture is unmistakable. Or, your constellation is more like a celestial map, with hundreds of stars individually beating from their tagged and labeled corner of the catalogued universe. Whatever floats your boat!
But skipping the outline altogether isn’t a good option—it’s a tool to help you with the writing process, and it’d be silly (or dangerous) to sail into open water without some stars to guide you.
Here are my outlining rules for you to outline your specific book:
Your outline should support your writing. Don’t do a big formal outline if you’re never going to look at it again, just because you think you’re supposed to. Think of your outline as a list of prompts and assignments—with a good outline, you’ll never sit down at your desk and feel blocked or like you don’t know what to work on next. If you think about it like this, you’ll free yourself from being overly concerned about the specifics of the structure. Like I said above, sometimes a lot of detail and perfect clarity is necessary, but most books aren’t that complicated, and you won’t need as many prompts for yourself. Be as detailed in creating your own prompts and assignments as is helpful to you.
Your outline can be any shape. You might have an outline in a google doc that looks a lot like the numeral outline you learned in school: I, ii, iii, like our first writer above. But it might look nothing like this. Maybe it’s a series of note cards laid out or taped up on the wall behind your desk, which you can move around to experiment with structural ideas. Maybe it looks more like a mind map, or a central word (the main subject) surrounded by rays that point to sub-topics surrounded by bullet points of detail. You might have bullet points under your chapter titles, or written summaries. It might not have chapters at all. Wow! A book can really be anything.
(Two of my writers are thinking about multimedia books—they’re not at the outlining stage yet, but laying out a multimedia outline is more like putting together a newspaper! Pretty cool stuff, and also a process that may involve other creators, artists, and writers. Anything can be anything!)
Use your lists. When it comes to finding those details, the items you’ll put in your outline, the stars of your constellation, you’ve already done it! Return to the amazing lists you’ve been making since the start of this series! (Links at the top.) These are the things you put in your outline, all the anecdotes, examples, scenes, digressions, descriptions, references, and character details.
Add notes, questions, and needs. You can also add notes to yourself about the material, like why it’s important to include so you remember what to write about, and questions about the material or structure you’re still figuring out. If you know you need to do some research for certain chapters, include the questions you have and the research you know you’ll need to do for that section.
Example outline snippet Part 1, ch 3 Scene: Danny bites a dog Importance: shows Danny's confusion about what kind of animal he is Backstory: we learn how Danny lost his hand Details: write about the fur in the teeth, make it disturbing. good metaphor for the sound of a man barking? Needs: read that book about species confusion, need quote about phantom tails Questions: should introduce the cat here?
The final need-to-know about your outline is that you can abandon it. The only rule more important than ‘never leave the boat’ is ‘sometimes leave the boat.’ Like Pip on the Pequod, you have to know when it’s time to jump ship. Your outline is not meant to imprison you in some bad idea that’s not working, or a structure that you realize after a month or two of writing isn’t actually the best way to tell the story. And the structure of a research-based book or a reconstruction of past events will emerge as you research and write. Your destination may even change as you get into the writing. If this happens to you, do not worry. Your book has to be a book that changes. Even the stars move in ‘proper motion,’ in case you didn’t know. Even Orion looks different than it used to.
Navigating the celestial map
Remember back in writing a book 1/ when I told you to list all the questions you have about practice and process and put them aside? Go get that list now! It’s time to figure out your navigation plan—how will I write this book? I have my outline, so what’s next? All of this:
Organize what you have. For weeks now, you’ve been making lists of everything you know about your book and all the things that’ll probably go in there. Now, you’ve also laid those bits out into a representative outline. Before you dive straight in to writing, you may have some organizing to do. Did you create your Book Place back in week 1, a space in Notion or google drive or Scrivener where you’ll keep everything you need for the book? Depending on the elements that make up your book, you might need a table or sheet to organize the materials you’re using, like photos, recordings, interviews, pieces of research, quotes, and references. If it’s helpful to organize all this stuff, now’s a good time. You might also have notes for your book scattered in different places—gather them together now.
Decide on your standard of practice. How much time are you investing in this book? You might not care about how long the book takes to write (“2-10 years” per Annie Dillard 😂), but you’ll still want to commit to some kind of practice in order to get the benefits of this writing life. Maybe it’s an hour or two hours every day, maybe it’s two hours on Saturdays, or maybe you want to work up to taking a month off so you can just write. People ask a lot about word count as a daily standard. That can be great for some people, but really depends on what phase of the process you’re in (see below). As you know from reading this newsletter, not every part of writing is writing, so I don’t want a demand like, “Write 2K words a day” to make you feel like you’re not making progress if you spend your time doing something else to support your writing. Maybe that’s reading or taking a walk or having a chat, or lying on the floor, you don’t know. Maybe you like to write a chapter and then edit it before moving on, which, to quote Bright Eyes, is one way to live. So I like to suggest ‘time spent’ as a standard.
Ritualize. Return to the writing rituals piece from a few weeks back. How will you incorporate ritual into your practice for this book, to help support and protect the standard you set?
Write in the order that makes sense.This is where your process questions come in—how are you going to approach writing this book? Your outline gives you a series of places to start, but where do you begin? You do not have to write chronologically according to your outline, from the first point to the final scene, but you certainly can if that feels good to you.
Think about interest. I usually suggest that you begin where you’re most interested to begin, or where you have the most energy or ideas. That might mean starting with the climax or the ending, then looping back around to the beginning.
Don’t think about the intro, probably. If your book has an intro, usually you write that last. Not always, though. You might write your intro first if it’s laying out the reasoning behind the book and would be helpful to articulate and do whatever research might help.
Think about phases. As you look at the needs in your outline, you might see how a phased process could help you. For your memoir, maybe it’s writing out all of the key scenes first, then going back to fill in context and reflection. For your guide book, maybe you’ll lay down the practices first and then you’ll have a phase focused on writing up the theory. If you have a lot of research to do, you might want to devote some amount of time to do that work, and then get into the writing. But don’t let that stifle you—you probably don’t need to complete all research and conduct every interview before you can start writing!
Think about accountability and support. Every Friday, I meet in a “writer’s support group” with my amazing friends Sarah and Fadeke. We’re all working on totally new adventures in our writing, and being able to hear what’s going on with them and be excited together is one of the best things about writing, and life! Think about whether a writing group is something you want to join or set up as part of your book-writing process and writer’s practice.
It doesn’t have to be a big group of people, either, it might just be one other friend you get involved with who’s also working on a book. Maybe you’ll meet once a week in a public place to sit across from each other and write, or maybe it’ll be more like my group, where no writing actually happens because we’re busy gabbing about writing and ideas.
Or maybe it’s a workshop you want, where a few of you bring chapters from your in-progress book to share and discuss with the group. You might not want any of these things! But if you do, think about who you might reach out to, just one friend to start with who you’d be stoked to spend some amount of creative time with.
Is there at least one person you can call, tell them you’re writing a book, and they’ll be really excited for you? Call them this week.
That’s all, folks, you made it through book prep! Please reach out with any questions about any of the editions of ‘writing a book’ I’ve shared so far. And let me know how your book is going!
We’re now navigating away from the book process and turning to the essay—I’ll share my must-do steps for starting any new essay or post next. (In case you’re curious, outlining for essays and posts is different from outlining a book—I have a bunch of specific recommendations and things to think about for essay outlining, so more to come on the world of outlines.) I’ll probably post another ‘thoughts’ edition next Monday.
And I’ll see you back here Friday for your next creative writing prompt!
As always, this newsletter is completely free—please share with other writers you think might love some guidance.
