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Today’s post is from my friend, Nat Eliason. Nat and I meet up once a week to write together. His first book, “Crypto Confidential: Winning and Losing Millions in the New Frontier of Finance” is publishing in July 2024 from Portfolio, the same division of Penguin that published the best-sellers Start With Why, The Psychology of Money, and The Daily Stoic.

Last year I received devastating news: 

I sucked at storytelling. And not just storytelling, I sucked at writing fiction in general. 

I had asked a friend to read a sample chapter of Crypto Confidential and he said, in the nicest terms possible, I really needed to improve my story structure, my suspense, tension, dialogue, basically everything. 

It’s a nonfiction book, but I wanted it to read like an exciting fiction narrative. So I dived into reading everything I could find on writing great fiction. Since then I’ve worked through dozens of writing books and my craft has improved significantly, and one that I keep coming back to is Stephen King’s On Writing. 

If you have any aspirations to write a novel, or just want to improve your writing and storytelling in general, it’s truly one of the best resources out there.

And today I want to share with you five of my favorite lessons from the book. 

Write Fast and Don’t Stop

You’ve probably heard the advice to write a “shitty first draft,” but you should also try to write that draft fast. As King puts it: 

“I believe the first draft of a book—even a long one—should take no more than three months, the length of a season… I like to get ten pages a day, which amounts to 2,000 words. That’s 180,000 words over a three-month span, a goodish length for a book—something in which the reader can get happily lost, if the tale is done well and stays fresh.”

Two parts of this stand out to me: 

First, this is a really short amount of time! He suggests getting an entire draft done in a season. Not a year, not half a year, a season. Three months. Think about where you were three months ago, that’s not that long ago, is it? 

It’s so easy to build up writing a draft in our head as this huge long project, but King thinks it should be fast. Don’t overthink it. Just write. You can edit it after you’ve gotten everything out. 

Second, he takes no breaks! Momentum is clearly very important to King’s process. If you do the math, you’ll realize that 180,000 words in three months is 90 days, so he’s writing 2,000 words on the weekends too. 

I have mixed feelings on this. I definitely welcome the break from my writing on the weekends, but I also notice that I’ve lost some inertia when I come back to it on Monday. Perhaps committing to writing every single day is actually easier than taking a break on the weekends. It’s worth a try! 

Keep it Simple

One easy way to get stuck while writing is to agonize over what word to use. You want to be descriptive and appropriately flowery and prove how smart and clever you are so you sit there and stare at your keyboard turning red in the face trying to summon the perfect word out of the ether. 

But King says forget all that: 

“Remember that the basic rule of vocabulary is use the first word that comes to your mind, if it is appropriate and colorful. If you hesitate and cogitate, you will come up with another word–of course you will, there’s always another word–but it probably won’t be as good as your first one, or as close to what you really mean.”

If you obsess over questioning each of your word choices as you go, you’ll never get your first draft done in three months. And worse, all those attempts at being clever might just be making your writing worse. So don’t worry about it! Use the first word that comes to mind, and if you want to improve the first word that comes to mind…

Read a Lot (Including Bad Books!)

King repeats the advice you already knew, that you must read a lot if you want to be a great writer:

“If you want to be a writer, you must do two things above all others: read a lot and write a lot. There’s no way around these two things that I’m aware of, no shortcut.”

But he continues with a twist, you don’t have to read ‘great books.’

“One learns most clearly what not to do by reading bad prose—one novel like Asteroid Miners (or Valley of the Dolls, Flowers in the Attic, and The Bridges of Madison County, to name just a few) is worth a semester at a good writing school, even with the superstar guest lecturers thrown in.”

Nathan and I have talked about this a few times, how we have learned a lot about writing from reading novels we don’t think are particularly great. And we’ve even recommended them to each other on occasion specifically because they aren’t great. 

The other benefit to reading less-great novels is that it’s inspiring. If that can get published… why not you?

There are Guidelines, but Not Rules (Except…)

King gives an array of useful writing advice in the book. Avoid unnecessary adverbs, don’t toss on unnecessary dialogue descriptors, skip the “zen similes” like “He ran like a madman,” or “she was pretty as a summer day.”

But he also makes it clear that there are tons of successful authors who fail to follow these rules. Open up any bestselling book and you’ll find plenty of counter examples. Even esteemed literary fiction often breaks these rules. 

Worse, if you try to follow them too closely, you’ll end up sounding stilted. The one rule he says you absolutely have to follow is being honest. 

“I predict you will succeed swimmingly… if, that is, you are honest about how your characters speak and behave. 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.”

Everything your characters do has to be believable from what your reader knows about them. As long as you are telling the truth, you can get away with breaking most of the other rules.

Find the Drafting Style that Works for You

King has such an unbelievable process for writing his books. Here’s how he describes it: 

“The situation comes first. The characters–always flat and unfeatured, to begin with–come next. Once these things are fixed in my mind, I begin to narrate. I often have an idea of what the outcome may be, but I have never demanded of a set of characters that they do things my way… why worry about the ending anyway? Why be such a control freak? Sooner or later every story comes out somewhere.”

Come up with a situation, a few characters, and then start writing and see where it goes. This is the “Discovery” style of writing you’ve probably heard of. You just discover where the story goes as you write it. 

I tried this and… it didn’t work for me. I ran around in circles for 20,000 words and got annoyed and threw it out. So then I tried the opposite: a highly detailed outline. And that sorta worked, but it also had its shortcomings. 

The real key is what King says later: 

“Much of it has been about how you can do it better. The rest of it—and perhaps the best of it—is a permission slip: you can, you should, and if you’re brave enough to start, you will.”

Don’t agonize over finding the perfect outlining style. If you’ve been reading about how to write a novel for months but don’t have a draft done, then you’re wasting your time! The important thing is that you treat all of these ideas and advice as a permission slip to start. Just get going, you’ll find what works for you as you go. 

I can’t wait to see what you write.

Nat (& Nathan)