What I learned about writing from studying 6 incredible writers for 9 years

my favorite writers favorite writing wisdom

Dec 08, 2023

Who’s your favorite writer?

If a name doesn’t immediately pop into your head, I give you permission to drop your phone and go grab a book off your bookshelf right now.

I managed to flip that problem on its head by having too many favorite writers because I read too much.

I’ll even admit something embarrassing to you as long as you promise to keep it to yourself — I became that loser who counted the books he read each year like he was training for the reading olympics.

I went from reading 0 books in 2014 to 88 books in 2022. Still waiting for my reader of the year gold medal to arrive in the mailbox….

So one of my new year’s resolutions is to read less in 2024.

Sorry, I’m getting distracted, that’s enough about me.

The upside of reading too much is that I’ve discovered a handful of incredible writers who have mastered their craft (and plenty of horrible writers who should give painting or basket weaving a try).

I did some research to see what they had to say about the craft, and to my surprise, they all had some wisdom to share. Even the horrible writers but I’ll exclude those.

I wanted to explore the question— how do you write words worth reading? Lucky for you and me, they had some thoughts worth sharing.

Hopefully this doesn’t violate any laws of the internet, but if it does, this was a good run while it lasted.

Here’s the accumulated wisdom of my six favorite writers I wish I had before ever putting pen to paper (more like fingers to keyboard).

Enjoy!

Nassim Nicholas Taleb: How I write.
The common fallacy is that if you want people to read you in the future, you must project something related to the future, focused on the contemporary and be as different from the past as possible –say by populating your work with space machines, high technology, and revolutionary ideas…
No, no; it’s the exact opposite. I stood the idea on its head. If you want to be read in the future, make sure you would have been read in the past. We have no idea of what’s in the future, but we have some knowledge of what was in the past. So I make sure I would have been read both in the past and in the present time, that is by both the comtemporaries and the dead. So I speculated that books that would have been relevant twenty years in the past (conditional of course of being relevant today) would be interesting twenty years in the future.
Another discovery I made then, and to which I have been adhering until the present. If you consider writing a creative endeavor, then avoid practicing it in mundane matters as it may both dull your vitality and make it feel like drudgery, work.

Morgan Housel: A Few Thoughts On Writing
You have five seconds to get people’s attention. Books, blogs, emails, reports, it doesn’t matter – if you don’t sell them in five seconds you’ve exhausted most of their patience.
Good ideas are easy to write, bad ideas are hard. Difficulty is a quality signal, and writer’s block usually indicates more about your ideas than your writing.
Impatience has increased with social media. Someone reading a book 20 years ago had few other distractions. Today a phone offers infinite, nonstop competition for your dopamine. Writers of everything from emails to books have to accept that reality.
Whoever says the most stuff in the fewest words wins.
Delete without mercy. Jason Zweig says, “you can never create something worth reading unless you are committed to the total destruction of everything that isn’t.”
Most good writing is a byproduct of good reading. You’ll never meet a good writer who doesn’t spend most of their time reading.
Good ideas can’t be scheduled. They come randomly, usually after you read something that connects the dots to an unrelated thing. A lot of bad writing comes from scheduled writing.
If you have an idea but think “someone has already written that” just remember there are 1,010 published biographies of Winston Churchill.
A powerful trick is writing something people intuitively know but haven’t yet put into words. It works because readers learn something new without having to expend much energy questioning whether it’s true.
Writing looks like a soft skill, so it’s easy for people in technical fields to ignore. But in every field, the person with the best story wins. Not the best idea, or the right answer, or the most useful solution. Just whoever tells the most persuasive story. A lot of good ideas are killed with bad writing.
No one wants a lecture. Everyone wants a story, which is anything that subtly puts data into relatable terms. It makes everything easier to remember and contextualize.
Writing is an art, and art is subjective. Novelist William Maughan said there are three rules to good writing. “Unfortunately no one knows what they are.” I actually think there’s one: write the kind of stuff you like to read. Writing for yourself is fun, and it shows. Writing for others is work, and it shows.

Derek Sivers: My writing process
Write all of my thoughts on a subject.
Argue against those ideas.
Explore different angles until I’m sick of it.
Leave it for a few days or years, then repeat those steps.
Hate how messy these thoughts have become.
Reduce them to a tiny outline of the key points.
Post the outline. Trash the rest.

Scott Adams: The Day You Became A Better Writer
Business writing is about clarity and persuasion. The main technique is keeping things simple. Simple writing is persuasive. A good argument in five sentences will sway more people than a brilliant argument in a hundred sentences. Don’t fight it.
Simple means getting rid of extra words. Don’t write, “He was very happy” when you can write “He was happy.” You think the word “very” adds something. It doesn’t. Prune your sentences.
Humor writing is a lot like business writing. It needs to be simple. The main difference is in the choice of words. For humor, don’t say “drink” when you can say “swill.”
Your first sentence needs to grab the reader.
Write short sentences. Avoid putting multiple thoughts in one sentence. Readers aren’t as smart as you’d think.
Learn how brains organize ideas. Readers comprehend “the boy hit the ball” quicker than “the ball was hit by the boy.” Both sentences mean the same, but it’s easier to imagine the object (the boy) before the action (the hitting). All brains work that way. (Notice I didn’t say, “That is the way all brains work”?)

David Perell: Riding the Writing Wave
Writing doesn’t just communicate ideas; it generates new ones.
Writing forces you to think. It’s nature’s way of telling you how sloppy your thinking is. The ultimate test of how well you understand something is how clearly you can explain it in writing — clear writers are clear thinkers.

Seth Godin: Write something
Then improve it.
Then write something else.
Repeat this process until you have a post.
Then post it.
Then repeat this process.
There’s no such thing as writer’s block. There’s simply a fear of bad writing. Do enough bad writing and some good writing is bound to show up.
And along the way, you will clarify your thinking and strengthen your point of view.
But it begins by simply writing something.

You’ll notice that some of their wisdom contradicts each other.

But that’s a good thing because it proves that there’s no one correct answer to the question — how do you write words worth reading?

Simply experiment and find what works best for you.

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