I started writing online in 1999, and I get asked a lot about how I became decent at it. The short answer is lots and lots of bad writing, but the better answer is that I learned to follow some basic rules.
I am going to share those rules with you now.
1. Organize your thoughts using an outline
I use outlines for presentations as well.
Good writing requires clear thinking.
When I set out to write or explain something, I capture everything I want to say into a structure. This is the outline I used for this piece.
Rewrite your outline until it makes sense as a sentence.
I then imagine that outline as a sentence that helps me crystalize what I want to say.
What I learned over two decades of writing is that you need to think clearly, write plainly, and alternate between short and long sentences for maximum effect.
This whole essay could be summarized as that one statement, and the fact that I clarified that in my mind before I started writing helps the essay flow. It’s the reason I know exactly where I’m going.
Readers can tell if they’re being lead somewhere with confidence.
There’s no way to hide disorganization with good writing. If you’re making it up as you go along, your reader will know.
Know what you want to say before you start.
In order to write well, you must first learn to think well.
2. Write in a conversational tone
Language is like running code on the reader’s mind.
To avoid peoples’ mental garbage filters, you should write like you speak.
The first sentence of this essay is:
I started writing online in 1999, and I get asked a lot about how I became decent at it.
That’s something a human would say to another human. Imagine if I had started with this instead:
Writing is one of the most important life skills you’ll ever develop.
That might be true, but normal people don’t talk that way. Sentences like this are the writing equivalent of Jazz Hands. They tell the reader to expect bullshit, and they tune out.
Obfuscation implies deception.
Embellishing is one of the primary tells that someone is lying.
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Natural writing conveys honesty and soaks deeper into the reader because only honest people can afford to be plain.
3. Be direct and concise
Eliminate unnecessary words, avoid adjectives as much as possible, and just plainly say what you want to say.
Don’t write, “He was very happy” when you can write “He was happy.” You think the word “very” adds something. It doesn’t.
Following this advice is really difficult. Just assume you’ll fail and plan to edit each sentence multiple times until you reach maximum potency.
4. Alternate between complex and simple sentences
Christopher Hitchens is the master of this.
It’s true that crisp sentences have the most power per character, but you get maximum impact by alternating between the complex and the simple. This is an art, but there’s also a shortcut.
Alternate between long and short sentences.
Here’s a brilliant example.
A good argument in five sentences will sway more people than a brilliant argument in a hundred sentences. Don’t fight it.
“Don’t fight it” lands so well because the previous sentence was longer. It’s the contrast that makes it click.
The alternation is not one-for-one; you have to adjust for readability.
Clear writing is only possible with clear thinking, so start with an outline.
Fancy language communicates deception, so write like you’re talking to someone.
Wandering sentences lose the reader, so be clear and direct.
Flow creates impact, so alternate between short and long sentences.
And finally, if this list had a #5 it would be to spend a lot of time practicing.
Writing is the best only way to get good at writing.
I’ll see you out there.
This guide is clearly focused on normal, “online” writing, such as for essays or a blog. Business, academic, and other types of writing might have different requirements, but I’d argue they could also benefit from a more direct and conversational tone.
There’s an interesting tradeoff between conversational writing and being concise. Sometimes you might want to say something is really, really funny—because that’s what you’d say in real life. Even if it uses extra words.
I am often asked how I’m able to organize my thoughts when I answer questions, and I always give the same answer: it’s because I spend a lot of time writing. This habit of organizing what you want to say is invaluable as a thinker. It forces you to actually have a destination before you start driving.
The post that changed my writing the most was by Scott Adams of Dilbert fame, called, The Day You Became a Better Writer. It’s probably still my favorite, including this piece of mine you just read. The advantage mine has is that it’s a methodology rather than just advice. I’d been admiring his writing for a long time before he wrote that post (a habit I’ve stopped since he became an unhinged Libertarian), but it was that piece that crystalized what I enjoyed about his prose. More
The Hacker’s Reason for Avoiding Clichés is an essay I wrote on why you should avoid common phrases. More
Writing with complex language is often a way to hide a lack of ideas in the content. You see this a lot in academic writing, where they spend nine pages of tiny font to convey three sentences.
Small fonts are an interesting trick used by people and institutions trying to maximize their status in the reader’s mind. Basically, the harder it is to get the message, the more the reader thinks of the content. Academic journals and many bloggers abuse this psychological fact by saying very little in a font that’s barely legible. Wow! I had to squint to read this! They must be super smart!