On Writing Better: 43 Things I Learned from My Insane 2 Years of Study
You'll wanna save this one
Two years ago I quit my other work commitments and went all-in on writing.
I knew I wanted to make Crypto Confidential the best book possible.
But I didn’t know how. I needed to dramatically level up my writing skills.
Over these past two years I’ve worked EXTREMELY hard to get as good as possible as quickly as possible to make the best book possible.
And I ended up learning more about writing in these past two years than in my 9 years of writing before.
With the book coming out in two weeks, I decided to try to distill everything I learned along the way.
If you have any aspirations to write a book, or just become a better internet writer, I hope something I learned can help you too.
This is a massive resource. It’s one of the longest articles I’ve ever written. So if you want to skip around, here are the main sections:
Adjusting from Article Writing to Book Writing
Improving Your Writing Productivity
Outlining and Organizing
Getting Better at the Actual Writing
Editing and Getting Feedback
Staying Sane
Let’s dive in.
One Quick Thing…
Crypto Confidential comes out on July 9th, but I’d like to send you a signed copy of one of the few remaining pre-print collectors editions of the book THIS WEEK.
Fewer than 150 of these signed Advance Reader Copies will ever exist, making them much rarer than any other edition of the book.
To enter to win one:
Pre-order the book anywhere (Hardcover, Kindle, Audible, other vendors)
Forward your pre-order confirmation to “cryptoconfidentialbook@gmail.com”
But you have to enter by 11:59pm Central on Thursday, 6/27.
I’ll randomly select five winners and announce them over email on Friday!
Either way, I’ll send you the first two chapters of the book and let you know about a couple other bonuses as launch day approaches.
If you already pre-ordered the book and sent your order confirmation, you’re already entered.
Okay, on to the advice…
Adjusting from Article Writing to Book Writing
Before I get into the meat of writing, editing, planning, etc. I want to say a few things about the mental adjustments you need to make going from article writing to book writing.
Write a Fucking Book
Books are an incredibly rare kind of product where if you do a good enough job with them, people will still be buying them after you die.
There's almost no other product in the world that can have that kind of longevity, except other forms of art like paintings or music.
So if you're going to write a book, write a fucking book. Don't try to bang something out in a few months, don't try to find shortcuts using Chat GPT or whatever to do the outlining for you, don't put it off until the last few months before your deadline with your publisher, write a fucking book.
If you take it incredibly seriously and try incredibly hard, harder than you've ever tried on any piece of writing before, it will have the potential to change your life.
But books follow an extreme power law. Most don't go anywhere, or they don't go beyond your existing audience. The only way it breaks out is if you commit to going far and above any kind of writing you've done before.
So don't rush it. Don't look for shortcuts. Lock in to spending 2, 3, 4 years on it. WRITE A FUCKING BOOK.
A Book is Not a Series of Articles
One of the first mistakes I made was thinking that if I could write a 2,000 word article in a day, writing a 70,000 word book was simply doing that 35 times.
It's not.
A good analogy here is the relationship between surface area and volume. Surface area scales as a square, but volume scales as a cube. An elephant is much more fragile falling from a great height than a mouse because there is so much more stuff holding the elephant together. It's easier for it to go splat.
A book similarly needs a lot of internal structure, relationships, organization, stuff holding it together that make it more complicated than a bunch of articles strung together. At least if you want it to do well. A book can be a string of articles but it tends to come out kinda disjointed and forgetful.
Be MUCH Simpler
One of the big challenges diving into Crypto Confidential was figuring out how to explain the crypt concepts within the flow of the book, without getting too in the weeds and without confusing people.
While my articles are fine being a little more technical, the book needed to stand on its own. It needed to appeal to a much larger audience.
I did a shit job of this at first. I had a chapter I was very proud of and I sent it to a dozen people and every single one (except the one reader who worked in crypto) sent it back saying they were completely lost.
Eek.
For any remotely technical topic, you have to go so much stupidly simpler than you think you do. Not because readers are dumb. But because you have completely forgotten what it is like to not have your own knowledge about the topic.
It is much, much better to leave some detail out and upset the top 1% of people in the field who will think you dumbed it down too much than to give a complicated topic the full treatment and alienate the other 99% of readers. If they want to learn more, they can always do it after.
A good analogy here is the planetary model of the atom. We learned in school that protons and neutrons are this massive center of the atom with electrons whirring around it like planets. That's not really true, but it works as a basic model to bootstrap your understanding so that you can go learn more about the finer details of how it works later.
Try to find the "atomic model" of what you're explaining to make it more digestible to a new reader.
But Don't Be Too Concise
Concision is a superpower in the frenetic online world, especially if you're making content for Twitter, TikTok, LinkedIn, etc.
But readers don't pick up a book (most books anyway) for the most concise information dump possible.
They pick it up for the experience of reading the book. They certainly hope to learn some things along the way, more if it's a very tactical nonfiction book. But if you just hand them a bulleted list of the most important takeaways they won't take anything away.
You have to create a book-reading experience, which is hard to do if you're still locked into your Internet concision-optimization mindset.
So draw things out. Create a story around them. Play with the reader's energy. Create some tension and suspense. You know, foreplay. Not only will it make the book more fun to read, but it'll make it more memorable too.
You Might Have to Let the Articles Go (for a bit)
As I got more into writing the book, I found writing articles was actively impeding my book writing.
For one, they took up creative time that I wanted to spend on the book.
But article writing is also a very different creative act than book writing, and it was hard to be in both headspaces at once.
So I decreased my blog publishing pretty dramatically. And while it was scary, it was necessary, and I’m very glad I did it. It’s okay if you can’t do everything at once.
Improving Your Writing Productivity
Experiment and Track to Find the Right Routine
There are plenty of opinions on when and how to write: early morning, late at night, in a cafe, alone, walking desk, bosu ball, caffeine, nicotine, mushrooms, beer.
But you'll never know what works for you unless you experiment and track.
When I committed two years ago to go all-in on writing, I started tracking every single writing session.
The time, location, words written, how I felt, etc. This is what inspired me to eventually make Prolific.
And I was surprised to learn that my best writing time was not early morning or late at night. I was slower in the morning, and too eager to relax at night.
My best time was actually 9:30am to around 12:00pm, and always out of the house. Writing in a cafe at this time period was a literal 1.5-2x increase in my words per hour, and I felt better doing it.
Great Writing Happens When You're Not Writing
Just like some of the best editing happens by not looking at the book, some of your best writing will happen when you're not writing.
If you're coming into a book project from a more go-go profession, you will feel incredibly guilty taking an hour or two a day to walk around a park aimlessly with no music or distractions and just a notebook.
But doing that is one of the best things you can do. You'll be overflowing with ideas from being in the low-stimulation environment, and you'll end up with tons of notes on what to do with the book that could help you with your writing tomorrow, or some future piece, or when you get to editing it.
But that only works if you...
Protect Your Subconscious
Your subconscious is incredibly smart and incredibly dumb. It will spit novel insights out of the ether as if they were shuttled to you by God, but it will spit out those insights about anything you feed it with.
So if you spend too much of your day arguing with people on twitter, clever comebacks are what it will spit out while you're walking.
Follow the news and it'll spit out doom and gloom about the world.
Pick up a side project and it'll spit out ideas for the side project.
The more stimulus you let into your life outside the book, the more junk your brain will spit out when you're in the shower or at the gym. So protect your subconsciousness's inputs at all cost.
More on this in "The Art of Fermenting Great Ideas"
Set a Daily Goal and Be Strict About It
As I got into my first draft, I eventually set the requirement that I had to write 2,000 words first before I did anything else that day. Usually I wouldn't let myself eat lunch or leave wherever I was until I hit those 2,000 words.
When I got into editing mode, I said I had to get through 4,000 words of editing before I could do anything else.
If you commit to getting your words done every day before you do anything else, you will make progress much faster than you thought possible. And you'll probably never run into writers block because you haven't given yourself all day to scuttle around distracting yourself with a dozen things along the way.
You Can Easily Get Through Writer's Block by Writing Shit
Every time I've hit writer's block it's because I'm too focused on trying to make it good right away.
So I gave myself permission to write dogshit every time I hit a bit of writer's block. Just get SOMETHING down and after a few hundred words you'll probably get back into the flow and it'll start to get good again.
A shitty draft is much better than an unfinished draft. So give yourself permission to write slop for a bit when you feel off and you'll find the writer's block naturally fades away.
Prime Yourself When You Wake Up
The first thing you do when you wake up in the morning is:
Look at what you wrote yesterday (but don’t edit!)
Look at your outline for where you want to go next
Look at some inspiration, either a writing book or a book you want to emulate
Then go about the rest of your morning routine. Ideally you do this a few hours before you actually sit down to write.
I usually did this around 6-6:30 AM, then I made my coffee and read and got my kids ready for the day. If I had any ideas for the book during that time period (which I always did), I captured them in a voice note on my phone (I like Superwhisper for this).
I didn’t sit down to write until 9:30, but by then my subconscious had been chewing on what I needed to do that day for 3 hours. It made it so that when I sat down, I was immediately ready to get started. In fact I was downright excited! I was ready to go! There was no warmup period or futzing around on Twitter and Email before writing, I would just dive right in.
Outlining and Organizing
Make a Proposal
If you want to trad pub, you have to make a proposal anyway. But even if you self-pub, you should make a detailed proposal for your book.
The proposal explains what the book is about, why now is the time to write it, why YOU should write it, who’s going to read it, how you’re going to market it, etc.
This might take a month or two to do it properly. The Crypto Confidential proposal took about two months to be finished (though not working on it full-time).
But this is very, very worthwhile time spent considering how much clarity it will give you on your project.
And it might make you realize that this is the wrong book, or the wrong time, or that you’re not really the right one to write it! That’s helpful to learn too.
You Need an Outline
The idea of "discovery" writing where you just start and see where the book goes sounds sexy and artistic and fun, but you'll probably end up going around in circles and never get anywhere that interesting.
At the very least you need a high level outline of where the book is going and how it's going to get there.
If you want to maximize impulsive creativity you could keep the outline concise, and only list the top ~10 major scenes that you plan to navigate through so you can figure things out along the way.
Or you could go to the opposite end of the spectrum and outline every single scene and every single beat within the scene and then start chugging through it.
Either way, you need something to keep you on track and to keep you from getting stuck along the way.
As eager as you probably are to skip to the fun writing part, investing a month or two up-front to really nail your outline is going to dramatically reduce your headaches along the way.
Try Many Outlining Styles
That said, there's no way to know what kind of outline will work well for you unless you try a bunch of them.
Digital tools like Scrivener and NovelCrafter might click.
You might like doing it in bullet points in a word doc.
You might make a database in Notion to organize all the pieces and their details.
You could use physical index cards and organize it on your floor.
You could put sticky notes all over a wall.
I’ve tried all of these and more. The index cards helped the most for Crypto Confidential, and for my Sci-Fi novel I’m finding NovelCrafter’s cards a great outlining tool. But each of these methods was also helpful in its own way at different times.
And you might find that when you’re stuck in one medium, say a digital outline. Translating it to a physical outline on your office floor gives you the clarity you need.
So try a bunch, use multiple, and figure out what works best for your brain.
Adjust Your Outline As You Go
The outline is an extremely helpful starting point, but you’re only going to end up following ~50% of it at best.
As soon as you start writing, you’ll realize something needs to be tweaked. That’s fine! Take a few minutes at the end of each writing session to look at your outline again and see if anything needs to be adjusted.
It will naturally evolve with the book and half of it will emerge from the writing process, but you should still have a full outline to get you started.
Proven Story Structures Are Helpful Scaffolds.
Looking for some proven story structures to try to fit your book into can be very helpful for creating the initial scaffolding. It will make sure you're hitting important major points like the inciting event, the climax, the midpoint (which does not mean middle, it means when the protagonist goes from being reactive to proactive).
There's the three-act structure, a classic most people are familiar with (though not that helpful for structuring).
There are more complex ones like The Snowflake Method.
There is the 7-point Story Structure (I rather like this one).
And of course the Hero's Journey.
But just keep in mind that these are scaffolds not foundations. You should use them to get the story going and to help come up with what your scenes and beats and turning points will be. But you shouldn't try to force your story to perfectly conform to them or it might become stilted.
Think in Terms of Scenes and Summaries
It’s tempting to think of your book in terms of chapters, but a chapter is more like a reading checkpoint and is usually not when the action briefly stops, or at least it shouldn’t be if you can avoid it.
If the action always ends at the end of a chapter, then your reader might not read the next chapter. By having part of the action not resolve until the next chapter, you ensure that your reader continues in to the next chapter.
The organizing unit to focus on is Scenes, not Chapters. A scene is essentially:
A continuous period of time (no time jumps)
In one location
With a character who wants something
And the result of whether or not they get the thing
But within the scene there must also be some conflict over the character achieving their goal. And for the reasons below about “keeping a reader interested,” it must not be an easy conflict.
A chapter is just a container for any number of scenes, with the occasional summary of other details in between them. And when you can, it helps to end the chapter in the middle of a scene so the reader wants to see how it resolves.
For example, in the first chapter of Crypto Confidential:
Summary: Quick background on how I’m learning programming and trying to day trade
Scene 1: I go visit my friend and discover his cafe has been broken into
Scene 2: I get to work trying to find someone to give me insider trading knowledge
Scene 3: I reach out to someone who might be able to help me, they agree and say we can meet tomorrow, and I’m left hoping they’ll share the information I need
Scene 3 technically ends at the end of the chapter, but the real payoff in Scene 4 where you find out whether or not I get the information doesn’t happen until Chapter 2, so there’s an incentive to keep reading.
And this works in Nonfiction too if you tweak it a little bit. A first chapter in a self-help book might be:
Scene: Story that captures some idea (with the character having some conflict they overcome)
Scene: How you the reader encounter that problem in your own life, the conflicts that get in the way of solving it, and how you can
Scene start: A teaser that this leads to some other problem, which will be explained through the story at the start of the next chapter.
Your book is a series of scenes that naturally flow from one to the next, with each one opening new questions and resolving them in the reader’s mind but which all service the overarching book-question they’re trying to answer.
Getting Better at the Actual Writing
Before I started working on Crypto Confidential I mostly knew how to write how-to explainer-style Internet articles (similar to this one).
But I quickly realized that while those kinds of articles are very useful as reference or educational material, the style is forgettable in book form.
Part of why people pick up a book is to have an experience, to get lost in something. And if you just throw a ton of facts and explanations at them they won't get immersed in the world.
So if you, like me, are accustomed to trying to be maximally efficiently helpful in your writing, you have to develop an entirely new skillset to write a good book.
I spent a good chunk of my self-education over the last two years focused on this. And while you can only really learn it through practice, trial, and error, there are some general tips and tricks that can help.
Practice Practice Practice
I don’t think I need to tell you this but the only way you’re going to get better is by writing a ton. Specifically, writing a ton of book-length work.
You don’t get better by reading twitter threads about writing, watching videos about writing, listening to podcasts about writing, you get better by writing.
Crypto Confidential went through five drafts, and the first two were objectively bad. But I needed to do that to get the reps in to start to get good.
So just be prepared for that. It’s going to take a lot of reps.
Pick One or Two Core Skills at a Time
There are a TON of skills you need to get better at to write a good book.
Structure, story-telling, dialogue, description, scene, suspense, explanation, character-building, word choice, energy flow.
If you try to get better at everything at once, you’ll get overwhelmed and not make much progress.
Instead, pick one or two things and focus all of your energy there first. And ideally, pick ones that are essential to writing a good book.
For me, I focused almost all of my energy on story-telling and suspense because if people are interested enough in a story, they’ll forgive other aspects of the writing being weaker. I’m still not great at description, a lot of my scenes lack detail, but that’s okay if the problem is interesting enough.
On the other hand, if you have a beautiful scene but there’s no problem the reader cares about, they won’t care about the scene. So maybe don’t start with description.
More Fast Drafts
I found it much easier to improve by finishing whole drafts of the book, picking specific aspects I needed to improve on, and then doing another draft specifically targeting those things.
You’ll also find, especially for your first book, that you get SO MUCH BETTER after each draft that you’re a little embarrassed by the beginning of your previous draft. That’s fine! Be willing to start fresh using the new skills you developed.
Pick Books to Model
Once you know what you need to get better at, pick some books that do it extremely well and read them over and over again. Or just read the first chapter from one of them each morning sa part of your “priming.”
I focused most of my energy reading fast-paced suspenseful fiction, not nonfiction books. I knew if I could model the style of Red Rising or A Time to Kill, it would make my book much more interesting.
If I had tried to model a finance textbook, it wouldn’t have been nearly as fun.
Study Study Study
I know I said that looking for writing advice isn’t making you better at writing, but once you know what aspect of writing you need to get better at, try to find a resource that will give you guidance on getting better at that thing.
For example, I knew my story-telling was weak, which is why I dived down the rabbithole of studying fiction writing advice. I got a ton of value from the books Scene and Structure and Conflict and Suspense because those were aspects of my writing I knew were weak, and I was able to immediately apply the lessons to what I was working on.
So study, but make sure that what you’re studying is directly related to what you’re trying to improve at so you can put the lessons to work right away.
Braiding is One of the Highest Leverage Writing Skills
If you’re totally lost on what to focus on getting better at, focus on braiding.
Narrative-style writing (fiction and nonfiction) has four major components:
Action: Things happening
Dialogue: What people are saying
Description: The environment around the people and events
Interiority: The characters internal reactions to the place and action
And you could add “Explanation” for certain kinds of nonfiction.
A bad writer will only focus on a couple of these. They’ll have lots of dialogue and action but no description of the environment and no thoughts from the character.
Or they’ll have this highly detailed world with tons of navel-gazing from the protagonist and no action.
A good writer will use all four of them. But they might get stuck on one for too long, like long chunks of description at the start of a scene, or long periods of dialogue with no action or description.
But a great writer will seamlessly flow between them, using each to their fullest and never getting too stuck in any one of them.
Go through your writing and figure out which of these you often forget about, and focus on weaving more of that into your writing. It’ll make a big difference.
Open Questions in the Reader's Mind
At the core of keeping a reader's interest is creating questions in their mind that they want answered.
Early on in a book, as quickly as possible, there needs to be some big question that gets planted in the reader's minds which they care enough to find the answer to:
Does Harry become a wizard?
Does Luke rescue princess Leia?
Do the Hobbits destroy the ring?
And then along the way, there need to be many smaller questions that pop into the reader's mind that relate to the big question:
Does Harry get one of the letters?
Does Luke find the droids?
Do the Hobbits make it to Rivendale?
And truly, the reader knows these things are going to happen in one fashion or another, so the question is more like how do these things happen.
But that has to be interesting too! Because if the questions are being answered in obviously predictable ways, the story will be boring. So you have to...
Move AWAY From the Goal
If the first letter appeared at 4 Privet Drive, Vernon handed it to Harry, he opened it, and then went "whoa I'm a wizard LFG!" that would be boring.
Instead the first letter shows up and Vernon destroys it. (Harry is now further from finding out he's a wizard).
Then more come and he boards up the mail slot and locks Harry under the stairs (now he's even FUTHER).
Then they start flying down the chimney and breaking through the windows and the Dursleys run off to a shack on an island to try to hide from them (now Harry is both further AND farther!).
And then BAM Hagrid shows up and breaks down the door and delivers the news himself.
This is a perfect example of how you can answer a question in the reader's mind by progressively increasing the stakes by moving the protagonist further away from the resolution, and then finally satisfying the reader with a surprise answer.
Imagine if they got to the island and Harry found a letter in a suitcase. That would be an okay resolution, but Hagrid breaking down the door and giving Dudley a pig tail is so much more satisfying.
And now that you've had a question opened in your mind which was resolved in a surprise, satisfying way, you'll want to find out how all of the other questions popping into your brain get answered.
Yes But, No And
The more you create satisfying surprises for your reader, the more interested they'll be. If they feel like they know exactly where the story is going and how the big and small questions will be answered, they'll get bored and quit reading.
One good trick to create satisfying surprises to resolve questions (I talked about this more in my forthcoming interview with David Perell) is the classic "Yes but, No and" tool.
A character should never get exactly what they want or what they're trying to get in a scene.
Instead, they either SHOULD get what they want BUT it has some unexpected consequence.
Or they should NOT get what they want AND it should have some additional unexpected consequence.
Harry DOESN'T get what he wants (the letter), AND he gets locked under the stairs.
Eventually he DOES get what he wants (whisked away by Hagrid), BUT he finds out the most powerful wizard in the world might be alive and trying to kill him.
Luke DOES find the droids, BUT he gets captured by the sand people.
Eventually he DOESN'T defeat Vader, AND he finds out Vader is his father.
This is one of those writing tricks where once you know it you will see it everywhere: movies, tv shows, books, and even though you know it's coming, it's still satisfying because it's very hard to predict what the "But" or "And" will be.
Dialogue Misdirection
One more trick just for fun. I'll do a longer post on all of these some other time.
The easiest way to keep dialogue interesting is to have someone's response occasionally shoot off in some unexpected tangential direction, often with no words at all.
For example, imagine:
Dudley: "Dad look Harry's got a letter!"
Harry: "Give it back, it's mine!"
Vernon: "No."
BORING. Right? The real final response after Dudley finds the letter and gives it to Vernon:
Vernon: "Who would be writing to you?"
That alone is good, but then you add his response:
Vernon: Looks terrified and stares up at Petunia, then back at Harry who gulps in fear
Now it's wayyy more interesting than a simple "no" because it opened this big new question in your mind: "What the hell is in that letter?"
Do Mini Writing Projects to Build Specific Skills
If you are in-between drafts and you want to get better at some aspect of writing, do a smaller project specifically focused on honing that skill.
During one draft-break for Crypto Confidential I started a thriller-y novel and got ~10,000 words into it, just so I could practice writing in that scary, stressful style.
During another one, I started a more literary novel so I could practice writing painful emotional situations.
These don’t have to turn into anything (though the first one inspired me to start my sci-fi novel, HUSK, and I hope to eventually do something with the second). They’re just meant to give you a sandbox to play in so you can practice whatever you’re studying without having to immediately apply it to the main project.
The Easiest Way to Make it Good is to Be Honest
Readers can tell when you’re faking it, when you’re trying to force a message, when you’re trying to show off, when you’re trying to make yourself look different than you are or when you’re trying to make a character act differently than they would.
So don’t. Just be honest.
From On Writing by Stephen King:
“Honesty in storytelling makes up for a great many stylistic faults, as the work of wooden-prose writers like Theodore Dreiser and Ayn Rand shows, but lying is the great unrepairable fault… If you begin to lie about what you know and feel while you’re down there, everything falls down.”
Good Writing is How You Break the Rules
I like to say that “good writing is the Grammarly fixes you ignore,” and it’s true. If you follow all the normal writing rules too closely, your writing will sound AI generated.
So keep all the rules in mind, but lean in to strategic places to ignore them.
For example, in Crypto Confidential, there are a couple chapters where I’m deep in the chaos and for parts of those chapters I have scenes that are entirely composed of disjointed bits of interiority and dialogue:
It would come back, too. The DeFi 2.0 narrative was just getting started. There’s always a bit of a lull in faith as these things take off. The early people have to take profits. But then everyone else will rush in and buy the dip.
*
“Nat, can you strap her in so we can go?”
“Hmm?” *screen tapping noises*
“Nat. Sutton. Car seat”
“Oh, yeah, yeah, one sec…”
*
You only have to double your money ten times to turn 1 dollar into $1,000. Or to turn $10,000 into $10 million.
*
“You made how much flipping Doodles?”
*Cackling laughter*
“Good work, that’s insane.”
“Clarks?”
“Yeah I could go for some champagne.”
*
Luna was flying again. Once we broke past $75, it could easily go to $100 or $200. It might be one of the best bets I made all year. Thank God I doubled down…
This is “bad” writing because there’s nothing to orient the reader, but that was intentional because I wanted the reader to feel disoriented here. I wanted them to feel as lost in time and space as I was.
Editing & Getting Feedback
The Most Important Part of Editing is Walking Away
I wrote Crypto Confidential in 5 drafts.
In-between each draft, I took three to six weeks off from the book. The first break was six weeks and they got shorter as I got closer to the finish line.
The first draft took about four months of work, but the subsequent ones all took 1-2 months. So I spent almost as much time not-writing as I did writing.
These breaks were ESSENTIAL to the editing process though. You would be amazed at what you figure out while you're not looking at the book, and when you subconscious can noodle on little problems or things you ran into.
I would also use that time to study aspects of writing that I thought I was weak at, which meant that when I went back for the next draft I had a whole new set of tools I could use to improve it with.
Finally, if you're as hard on yourself as I am, the breaks give you time to cooldown a bit and stop thinking that it's complete shit. Then when you pick it back up you'll realize it wasn't as bad as you thought and feel much better about the whole thing.
Give Readers Less to Edit
It's tempting to try to finish a whole draft and then give that draft to people for feedback.
Don't do that.
For one, your first draft is going to suck. It just is, and that's fine. And it's probably going to suck for consistent reasons.
My first draft sucked because:
The story was disjointed and poorly paced
My storytelling was weak
I was way too confusing and in the weeds
My scene descriptions sucked
I had too many plotlines
Most of that (except for number 5) could have been figured out by reading one chapter. So especially in the beginning, don't ask for feedback on the whole book. Pick an early chapter you think is your best one and show that to people, and then assume that anything wrong with it is extra wrong for the rest of your book.
As a bonus you'll get much faster feedback this way, too.
Don't Edit Before You're Done with a Draft
On that note, don't waste time editing ANYTHING -- not even a misspelled word -- until you're done with a full draft.
When I finished the first draft it was about 100,000 words. The first thing I did was go back to the beginning and delete the first 30,000 of them. They were boring and unnecessary but I had to finish the book to realize I didn't need them.
If I had spent ANY time editing those words it would have been a total waste.
I'm pretty convinced this is the big bottleneck for most people with finishing a book in a reasonable amount of time. They write some, then they edit, then they write, and they edit, and it ends up taking forever to finish a draft. Don't do that. Finish the draft, then let it sit, then edit.
Write Down What You Think People Will Say Before You Ask for Feedback
The more you can train your intuition about what's wrong with your work, the better it will be, and the faster you'll be able to work. But you can't train that intuition without testing it against the market.
So before you send something off for edits from anyone, write down what you think they'll say is wrong with it, then compare.
If you think something is wrong and everyone else does, then it's DEFINITELY wrong. But there might be things you think are wrong that no one is bothered by, which could be just a small preference or a symptom of perfectionism.
You might also find that everyone thinks something is wrong which you had no idea of, and that's a wonderful blindspot to be made aware of.
Ask People What They Like
When you send stuff out for edits, also ask people what they like. It might give you clues on how to make the rest of the book better.
I thought I was getting too in the weeds with some of my philosophical debates in the sci-fi novel I was working on but no one complained about it and a few of the readers said they loved it. So contrary to my expectation, I should actually do more of it. Not less.
Readers Are Right That Something Is Wrong, But Wrong About How to Fix It
If your readers are telling you something feels wrong with part of the work, listen to them. They probably have a pretty good sense of something being "off."
But unless they're authors or professional editors, they probably don't have good ideas on how to fix it. So just smile and nod and say thank you when they give that part of their feedback, but then feel free to ignore it.
Or suggest some of your ideas on how to fix it and see how they react, if one of the ideas lights them up it might be the right more.
And if you're editing someone's work, it's totally okay to just say "something was wrong here" or "I didn't like this." That's very helpful!
If It's Not Painful, You Aren't Cutting Enough
People rarely complain that a book is too short.
But often complain that a book is too long.
There are going to be parts of your book that you really, really want to keep, but have to cut to make it fully focused on the main story you want to tell, or the main point you want to make.
The first draft of Crypto Confidential was 100,000 words. Then I cut it down to 70, built it back up to about 100, cut it down to 90, then I thought I was done with it.
But I had a feeling I could make it a little tighter to have that extra bit of confidence that more people would finish it. I went through it with a fine-tooth comb and cut another 8,000 words to get it down to 82,000.
Some of those 8,000 were unnecessary paragraphs, but it also included a couple stories that I loved and wanted to include but they just weren't essential to the main story, so they had to go.
The last round of edits should be PAINFUL. If you're only cutting material you want to cut, you're not cutting enough.
Re-Outline Before You Edit
Once you finish a draft, let it sit, and get some feedback, don’t immediately start on the next draft.
Instead, first re-outline the book. Don’t assume that everything you have in it should still be in it. Some chapters might need to get cut, and new material might need to be added.
Zooming out and making a new outline to fit your existing pieces into will ensure you’re not being too attached to what you already wrote.
Don’t Edit the Draft, Make a New One
Especially if you’re coming from article writing, it will be tempting to try to edit your draft within the existing doc.
But if you do this, you’ll make fewer changes than you probably should. You won’t be going over it with a sufficiently fine-toothed comb.
Instead, make an entirely new document and start from the beginning. You don’t have to type everything out again, but at least for the first few drafts, copy your paragraphs over one-by-one so you’re sure you really want to keep them as they are. The act of reading, copying, and pasting will slow you down and make sure you give each piece of the book the attention it needs.
Staying Sane
Writing a book is a marathon, and just like you need proper nutrition and hydration and stretching and everything else to get you through a marathon, you need some mental and emotional support to get through the book writing process in the best shape possible.
Here are some things I found that helped.
Track Everything
I tracked just about every single writing session from the day I started on the book.
I did it in a variety of spreadsheets, then ended up building Prolific because I wish I’d had an app where I could track it publicly.
Since you’re going to work on this thing for a year or longer without getting to hit publish, it’s hard to feel like you accomplished anything at the end of most days.
But if you can look at your spreadsheet or Prolific history from the last few weeks or months, it becomes immediately obvious just how much work you did. It makes it much easier to give yourself credit, and you’d be surprised how big of a difference that can make.
Make Artifacts
Every time I finished a phase of the book, I made sure to set aside that phase in a physical artifact so I would have it forever.
I printed out each draft and got it spiral bound, and I boxed up the first three outlines of the book since I did them on index cards. I also saved the journal I took most of my notes and thoughts in during the period.
I want to find a cool chest or something to put this in, along with a first ARC and first print of the book, so that even in thirty or forty years I can open it up and look back on this period.
It’s also a good visual reminder of how much work you put into the project. I love seeing it next to my desk while I’m working on the next book.
It’s Okay to Ask Someone to Tell You You’re Good
It’s more than likely that at some point you’re going to feel like the whole thing is shit and you should just throw it out.
I was feeling awful about the book in November 2022 so I sent a few chapters to my editor, asking him if there was anything there. His response was:
“Nat, these are great. Seriously—you’re nailing it.
Obviously diving in like this mid-story I have lots of questions, but coming in pretty cold, I think it’s terrific. It moves swiftly, explains technical stuff clearly, and it’s got your voice and spark. I really dig it…
My gut is to let you keep on keeping on until you’ve covered more ground.”
He had some other more tactical feedback, but this validation was all I needed to hear to rekindle my motivation to keep working on it.
When you feel really down on your work, take one of your best chapters and send it to your editor or a friend and just ask “do you think there’s something here?”
They’ll probably think it’s much better than you do. It won’t be perfect, but you know it’s not perfect. All you need to hear is “yes, there’s something here, keep going,” and you’ll feel much better.
“Can Be Better” Does Not Mean “Bad”
If you’re as self-critical as I am, then you won’t be able to look at your work without seeing all the ways it could be better. All the ways it isn’t living up to your expectations, or needs to be tweaked, etc. etc.
That’s okay. In fact, think for a second about your favorite book. Now tell me one thing that could be better about it. If you’re a writer, you can almost certainly name a few:
I LOVE Three Body Problem, but the characters are kinda flat.
I LOVE Dark Matter, but the science kinda breaks down at the end.
I LOVE Altered Carbon, but the sex scenes are some of the weirdest, most uncomfortable things I’ve ever read.
None of this makes them bad books. They’re all great books! Just because there’s some aspect of your work that can be better doesn’t mean it’s bad.
There will always be room for improvement. So start getting in the habit of saying “this is great and I can make this piece better.”
And, eventually, you’ll have to say “It’s good enough.”
‘Art is never finished, only abandoned’ - Leonardo Da Vinci
Find Friends
Writing is lonely work, and writing a book is extra lonely because you’re not getting to share a finished product very often.
So try to make friends with other people writing a Fucking Book. Get together to co-write once a week, with the strict rule that you’ll talk for ~30 minutes then not bother each other for the next two hours.
My friend Nathan Baugh and I have been writing together almost every week for over a year, and we’ve learned so much from each other along the way. Paul Millerd and I will occasionally get together too.
Anyone with a normal job won’t get what you’re going through. An entrepreneur won’t get what you’re going through. Your partner will try their best but they won’t entirely get what you’re going through.
So find another weirdo who does and hang out with them.
And if you ever have questions on the book writing process, shoot me an email (nateliason at gmail).
I can’t promise I’ll be your weirdo. But I will help how I can.
Thanks for reading! Don’t forget to pre-order Crypto Confidential and forward your confirmation to cryptoconfidentialbook@gmail.com to be entered to win one of the 5 remaining collectors edition copies.
Thanks for taking the time to write (and share) this. I’m in the process of shifting into book mode right now, and you’ve included some things in here that are right on target for me.
Loved this