How Does a Manuscript Go From Good to Great?
A framework to help writers make the leap
This week, I read the first five chapters of a manuscript by a writer working on her fourth nonfiction book. Diana is proud of her previous three books, she is becoming known for them, and at least one of them is selling well.
“But I don’t think any of these books are my best work,” she said. “I don’t think any of them are great. I’d like this new book to be great.”
“Do you think it’s on the way?” I asked.
She shook her head. “I kind of hate it,” she confessed.
The manuscript was due to her publisher in five months. The pages I read were at that moment sitting on her editor’s desk awaiting attention. It would have been so easy for Diana to just put her head down and finish a book she didn’t love, but she didn’t want to do that.
What is Great?
Each writer needs to define what great means for them. Diana told me that she was jealous of Oliver Burkeman’s Four Thousand Weeks, so we pulled out that book and looked at it together; we read the opening pages out loud.
“What is it about this book you like?” I asked.
“The beautiful writing,” she said.
The writing really is beautiful, and it’s instructive to show you what I mean because it it matters to this discussion. Examples from Burkeman’s book. include:
The title of the introduction is: In the Long Run, We’re All Dead. That’s a great title. It’s so blunt that it’s funny. But it also reminds us of the inescapable fact of life we all share. In just seven words, Burkeman gives us something to think about, something to worry about, and something to feel.
The first sentence of the book is: “The average human lifespan is absurdly, terrifyingly, insultingly short.” That’s a great sentence. It’s propulsive. The word “insulting” catches our attention because it’s so unexpected — who has ever thought of the shortness of life as being insulting? There is a specific point of view wrapped up in the word and it feels like a rallying cry.
On page 5, he writes: “The world is bursting with wonder, and yet it’s the rare productivity guru who seems to have considered the possibility that the ultimate point of all our frenetic doing might be to experience more of that wonder.” That’s a great summary of the point and positioning of the book. “Productivity guru” is opinionated and juicy. (Is he not one? How will he be different?) And the use of the word “wonder” is so lovely and hopeful. The world is bursting with wonder! Yay!
In the appendix, which in a strange way is the heart of this book, he writes: “Decide in advance what to fail at.” That’s great advice. It’s different from the "fail fast and often” advice of the tech world or the “failure is a part of success” anecdotes so commonly sad by successful people. It has a level of intention to it. You get to decide what to fail at and you should.
In addition to such precise and provocative sentences, Burkeman lets his stories breathe. He spends pages talking about farmers in the days before timepieces and a book called Technics and Civilization published in 1934, but somehow none of it feels self-indulgent — bits of information he thinks are interesting but leave the reader scratching our heads. It all feels relevant and critical to the argument he’s building. He is not rushing through material the way we often do in newsletters like this one or on podcasts or blog posts or articles. He is taking time, because (I assume) he is confident his readers will spend a portion of their four thousand weeks with his pages.
You can feel Burkeman’s authority. It’s seductive. You want to go down the path where he’s taking you. And it’s why books are a uniquely powerful form of communication.
Diana wanted to write like that. She wanted to write a book that has a place on the front table of the bookstore. She said:
I want my book on the opening table as you walk into the bookstore smack between the other trending and time-tested best sellers. On the left will be David Brook’s book How To Know a Person on the right Anna Lembke’s Dopamine Nation. Behind my book will be a stack of Anne Lamott’s heart warmers and in front, Pema Chodron’s wise When Things Fall Apart. I want my book to be the one of the few that readers won’t clean out from their book shelves when they do spring cleaning, and the one they can’t find because they keep loaning it to their closest friends, clients, and co-workers.
The Opposite of Great
There is a saying I heard from the great story expert Robert McGee way back in the day when I took his story structure workshop. He was talking about what makes a great antagonist and he said to look outside of the obvious opposites (good/evil) for the third thing to define the character. He said, “The opposite of love is not hate; it’s indifference,” which comes from an Elie Wiesel quote:
“The opposite of love is not hate, it's indifference. The opposite of art is not ugliness, it's indifference. The opposite of faith is not heresy, it's indifference. And the opposite of life is not death, it's indifference.”
By this measure, the opposite of a great book is not a bad book, which is a book that does not have the necessary components to be readable. It’s a book that readers feel indifferent about.
For shorthand, let’s refer to this as a good book, since it’s neither bad nor great.
Diana’s manuscript was indeed good. She’d done a great deal of research and thinking. She’d pulled together some good stories and exercises. She cares deeply about her topic. She wants a transformation for her reader. She’s a solid writer. But there was a sense of flatness about it. It felt like it lacked energy or life. I worried readers might feel indifferent — as if they had read the book before, as if they didn’t really need it.
I told Diana that there was nothing wrong with her pages — which was true. She could proceed with the edit that was imminent and write a good book. Or she could try to make it great.
“I want it to be great,” she said, “But how do I do that? I have five months.”
No one can wave a magic wand and secure a place on the front table. There are a thousand things that have to go in the writer’s favor for that to happen, some of which are wholly out of your control.
But greatness is something you can strive for by controlling what you can control.
How to Get to Great
There are three things a great nonfiction book (and certain kinds of memoir) has that a good book does not. Another way to think about this is, Why is Oliver Burkeman’s book so good? What does it have that a bad or merely good book lacks?:
A conceit or structure that lifts up the material
Curated stories that are well-told
An authoritative voice
Note that the requirements of greatness in fiction are very similar but for the second element, the stories the writer chooses to tell are in service of well-developed characters engaged in some kind of struggle for something they don’t yet have.
These three elements are best baked into a book from the start (which is the entire premise of my Blueprint framework (which you can learn about at jennienash.com/blueprint and which Substack is not letting me link to right now) but that doesn’t always happen in the real world. You don’t have to throw out an entire manuscript to get to great, but you do have to be willing to do some heavy lifting.
Diana agreed to do it. Here’s what we did:
1. Developed a New Structure
Diana didn’t like the framework she had built her book on—a process for aligning one’s values with one’s effort, which she calls Wise Effort. (Diana is a psychologist.) That’s why she was hating the whole book; it was built on shaky ground.
So often, when experts sit down to write books, they design convoluted frameworks for explaining their ideas because they are trying to design and write at the same time — a wildly inefficient process.
I asked her to walk me through the framework because it didn’t make sense to me, and she said her editor had questioned it, too. She was starting to wonder if it was all wrong.
We took out a big pad of paper and brainstormed new designs as she talked to me about the Wise Effort process. Instead of a four-square framework, maybe a target made sense? Maybe a teeter-totter would work? Maybe a swing?
“It definitely has motion,” she said, “it spirals.”
“So, um, a spiral?” I asked.
We drew two different spirals that go in different directions and have different qualities and I could see Diana lighting up. The spirals gave the reader a clear understanding of the big concept in a way the foursquare did not.
We created avatars for three people in her target audience and moved them through the new framework. Would it work for this person? What about that one? What about the other? The answer was YES!
Within about an hour, we’d landed on a more effective way for Diana to describe the work she is so passionate about. (Note that this is really fast and — true confession! — Diana and I cheated the process: I had just spent a week at a retreat she had led and had been immersed in her teaching. I had “lived” the confusing nature of her framework and knew that the possibility of something more elegant was there. Under normal circumstances, this kind of breakthrough takes several coaching sessions.)
The beauty of landing on the right framework is that it dictates the structure of the book. The path forward for someone doing the work of learning about Diana’s Wise Effort practice would be the path of the book. When we laid it out as a TOC, it had an elegance to it that the original book lacked. This is the second element of a great book — a conceit or structure that lifts up the material.
We talked about how Diana could use the new framework on her podcast, in her speeches, in corporate workshops, and on week-long retreats. It could contain all the work she wanted to do in the world. The new framework would bring all parts of her business into alignment. This is critical for an expert who is seeking to become a thought leader and/or to create a “brand.”
Diana was so excited about the new framework that over the next few days, she used it to shape a podcast episode, and ran it by her husband and a trusted client. Everyone loved it, probably because they could see that Diana was owning it, which is how you gain authority and voice.
2. Poured the Existing Content Into the New Structure
We started with the first five chapters of the book to see how much of the original content we could use in the new framework.
We set a rule: Moving a piece of writing over to the new TOC meant it had to pass a test. It had to serve the new structure and help Diana tell the new story she wanted to tell.
We moved approximately 75% of the material from the original five chapters and most of that material did not land in the same place or the same order.
This meant a lot of new text would be needed — bridges between things, introductions, and conclusions. We made a bullet point for Diana to go back and fill in later, but even without it being fleshed out, you could feel the flow of the material. You could feel that it had new life.
3. Defined the ideal reader
We worked on refining Diana’s ideal reader. The three avatars we had worked with when sketching out the framework helped us see what characteristics they all shared — and why they might need a book like this one.
Diana’s original target audience was too broad; it’s part of the reason her pages were flat. In speaking to so many people, she wasn’t speaking directly to anyone.
4. Made sure every story speaks to the ideal reader
With a better grasp on her ideal reader, Diana was able to curate the stories she told in the book. Rather than sharing random interesting stories about her mentors, her clients, and herself, each story was carefully chosen to make a specific point along the path of the framework. If a story didn’t serve the new framework, we tabled it.
5. Helped the writer claim their voice.
This step is the most important one — and the most intangible. What even is voice and how does someone claim it?
A lot of nonfiction writers come from academia, where the name of the game is citing and referencing everyone else’s work. Or they come from a journalistic or scientific tradition, where verifiable facts are the most important part of any piece of work. To claim their voice, these writers have to learn a different skill.
I’m not saying writers should ignore proper citations and factual content — that would be irresponsible, reckless, and wrong. I’m saying that writers also need to find a way to believe that they are the authority (the author of the book) and they know what they know better than anyone else, and they know where they want to lead their readers. This authority — this unique, confident way of speaking about their topic — is what lifts a book from good to great more surely than anything else.
Writers need to claim their right to speak up and speak out — which turns out to be far harder than it seems. Sometimes you have to poke and prod them to tap into the rich vein of their knowing: what do you believe about this, what do you say to your clients/business partners/patients, how do you get someone to understand the concept you’re teaching?
You can hear it — which is one of the reasons book coaching is so effective. In listening to the writer, you can identify their energy and passion.
When Diana talks about Wise Effort off the cuff, she knows all the answers. She’s filled with excitement and energy. She sounds like she owns this material. But when she first went to put it on the page, she tightened up. She got careful and deferential. Her book was not (yet) great because she gave up her power.
I invited her to unleash her powerful voice on the page — to just go for it, as if she was up on a stage leading people through a transformation — and it was right there, just waiting to be free.
6. Fleshed out the new text
Diana began work on putting her book back together, with a new framework, a new point of view, and a new authority.
Is the Book Great?
It might be! Diana has a lot of work to do, and many hands will work on the book to bring Diana’s vision to life (beta readers, book coaches, editors, proofreaders) but the new manuscript has a shot at greatness, whereas the original manuscript was condemned to just being good.
The best indicator of potential greatness is that Diana no longer hates the book. She is writing forward with joy — and for me, there is nothing that brings me more satisfaction.
Loved reading both of the backstory posts of your work with Diane!
An insightful read, thank you.