I started writing online in Spring 2013. In the five years since then, I’ve published a few hundred thousand words of content across this blog and my other projects, but I haven’t published an article about writing. There’s a certain self-consciousness about writing about writing. Writers suffer perpetual insecurity about the quality of their work, and I’m no exception.
While I still feel unqualified to tell you how to write better, I decided it could be helpful if I shared the advice that’s helped me improve. Some of this is personal. Not all of it will work for you, and none of it is true 100% of the time. But by reading through my notes, you might find a few bits of knowledge you can bring back to your own craft.
I’ve broken this out into sections focused on different aspects of writing, and plan on adding to it over time. The last update was on March 19, 2018. If you have found or heard any other useful advice I could add to this list, feel free to let me know on Twitter.
The best way to improve your word choice is to focus on what to remove, not what to add. These are the words we use in casual conversation that clutter our writing and impede its flow. Some of them are common (just, that, actually, pretty), some will be more personal (I use the words “great” too much). I’ve gotten better at spotting them over time, but I also keep a list of “banned words” to search my writing for once a draft is finished.
Sometimes, removing a word is difficult. “That” is particularly challenging to cut out in some cases, but I find if I take a moment to restructure the sentence to not need it, the sentence always sounds better. Others are easier. You can safely CMD+F for all instances of “pretty” and delete them unless you’re writing about your significant other.
This list is ever-lengthening, but here are my current “banned words”:
Now, some of them you need to leave in at times. But when you notice one being used, try to think really hard about whether or not it’s necessary. I like how I used “really” in the last sentence. I don’t use it often, so it has power when I do use it. I also think “like” was appropriate in the last sentence since I’m using it to express preference, not similarity. You get the idea.
This one is simple: delete your adverbs. If you’re not sure what an adverb is, the easiest way to identify them is that they frequently end in “-ly.” This is, again, more about extreme pruning than outright abstinence: you can still use adverbs, but save them for when they mean something.
For comparison, here’s how the last paragraph might look if I left in all the adverbs my hyperbolic brain wants me to use:
This one is also pretty simple: delete your adverbs. If you’re not really sure what an adverb is, it’s typically any word that ends in “-ly.” Like “typically.” This is, again, really more about extremely pruning your adverb use than completely abstaining from their use. You can still use adverbs occasionally, but save them for when they really mean something.
The extra adverbs change the feel of the paragraph. It’s cluttered, slower to read, less mature. It makes the writer sound like a high school girl from the valley. You don’t want to sound like a valley girl, do you?
Conjunctions at the start of sentences are fine. It sounds nice, and it helps the reader since it makes it clear you’re modifying what was said in the last sentence. But don’t overdo it. Used too often, it can sound awkward and like you aren’t speaking in full sentences.
If you use a less common word too often, your writing starts to sound odd. When writing, and especially when editing, make sure you aren’t using the same word too frequently. Don’t repeat an uncommon word in the same sentence, ideally not in the same paragraph, and possibly not for the rest of the section.
This is my favorite writing “hack.” As you’re writing, put “TK” anywhere you aren’t sure of a detail, or where you need to add more context later. One of the main reasons I stop writing or fall out of flow is getting stuck on some detail giving me trouble, and by dropping in a TK to come back to it later, I can maintain the flow.
Why TK? Think of it as “To Come.” That letter combination doesn’t appear in any English word, so when you CMD+F for it after you’re done writing, you’ll only find the instances where you used it as a place marker. Unless, of course, you wrote a paragraph explaining what TK means.
My biggest challenge, besides making time for writing, is avoiding writer’s block. The best preventative measure I’ve found for this is the “mega outline.” A mega outline is simply an outline you continue adding to until it’s too painful not to start writing the first draft, or until you’ve written the entire first draft within the outline.
Sometimes, a piece will jump out of the outline before I’ve finished planning and I’ll be able to dive right into the first draft. Other times, like for this article, I keep adding and adding to the outline and then all of a sudden I have a whole article in bullet points. I find it’s easier to skim through an outline and add ideas as they pop up than it is to write in a purely linear fashion, so if you’re having trouble on starting a piece or continuing one, keep adding to the outline.
You should keep a running list of all your active article ideas, and prune out any you haven’t thought about for a while. I do this in an Evernote notebook, where I add a new note for each article idea.
Most of them look like this:
That’s a “fresh” one. Others that have been percolating for a while will have some notes thrown in:
Every week or two, I go through my article list and delete any that don’t have any notes, that I haven’t thought about recently, or that I don’t feel strongly about keeping. Since I might add as many as a dozen new ideas each week, this is essential for keeping the list manageable. It only has 43 ideas in it now, which I can scan through in a minute when I want a new topic to write about.
The first couple paragraphs of a new piece always create a big source of procrastination and writer’s block for my pieces. The best solution I’ve found is to simply throw something down on the page to get started, and then go back and fix it up later. The intro is always easier after the piece is written, but you need to put something down to get started.
Another technique you can try is to simply delete your first couple paragraphs and use the third or fourth paragraph as your starting point. You’d be surprised by how often it works.
The easiest way to deal with almost anything giving you trouble is to delete it. If a sentence is bugging you, delete it. Awkward paragraph, delete it. Confusing section, delete it. You’ll find you never needed it in the first place.
The common advice with editing is “don’t edit while you write,” but that’s too simplistic. I like editing while I write it helps me think. Sometimes, you’ll get too hung up on editing and need to make yourself keep writing instead, but don’t worry if you want to edit while you write. There are no real rules.
If you can, try editing in a few different contexts, the more varied the better. Do one round of edits standing at the desk you work from, then do another at a bar after a glass of wine or two.
Looking at a piece in different places in different mental states will help you see it differently and develop a more varied voice throughout the piece. You may find, too, that when you look at it in a different context, you think of other material to include you hadn’t thought of before.
Most of us speak in longer or shorter sentences, and that will tend to come through in our writing. But if you monitor the length of your sentences, and force yourself to make some of them shorter or longer (depending on which you default to), you’ll make your writing sound more interesting. I like long sentences. But a short one every now and then helps make my paragraphs more readable.
Don’t try to fluff up your writing with more elegant prose. It never comes off as smoothly as you hope it will, and readers can see through the forced eloquence. Instead, write like you speak. Use whatever words come most naturally to you.
Now, this doesn’t mean you can’t start writing more elegantly, but you’ll need to change how you speak as well. Sam Harris is a good example of this. His writing has a certain elegance to it:
“Like most gun owners, I understand the ethical importance of guns and cannot honestly wish for a world without them. I suspect that sentiment will shock many readers. Wouldn’t any decent person wish for a world without guns? In my view, only someone who doesn’t understand violence could wish for such a world. A world without guns is one in which the most aggressive men can do more or less anything they want.” – Sam Harris, The Riddle of the Gun
But it’s also how he speaks. If you want to write more eloquently, you’ll need to create a corresponding change in how you speak, or else your writing will come off awkward and forced.
If you’re writing, then it’s obvious you’re what you think and believe, so there’s no need to preface every assertion with “I think” or “I believe” or “it seems.” Omitting those statements feels weird sometimes since you don’t want to come off as too cocksure, but foregoing them sounds better and makes your points stronger.
You could say: “I think workout machines are a waste of time because it seems like they focus too much on isolated movements and you lose the subtle benefits of larger, compound movements.”
Or you could say: “Workout machines are a waste of time because they focus too much on isolated movements and you lose the subtle benefits of larger, compound movements.”
The latter is far superior.
You can delete “to be” in most instances it crops up. For example, if you have a sentence that says: “It has to be a good deal.” You might rewrite it, “It must be a good deal.” Or simply, “It’s a good deal.”
Or if you have a sentence like “there is going to be a party this evening.” You might rewrite it “there will be a party this evening.” Or “we’re having a party this evening.”
If you’re trying to describe a certain type of person in an article, create an avatar for them instead of talking about them in the abstract.
Venkatesh Rao did this well in his article on The Premium Mediocre Life of Maya Millennial. On the surface, Maya is a single character, but she represents a demographic his readers can relate to. I did this in my Level 3 Thinking article by introducing the SHIBA avatar, the Stuyvesant-Harvard-Investment-Banking-Analyst archetype so many upper-middle-class young people fall into.
Creating people and avatars helps by personalizing what you’re trying to describe. You want to make the type of person you’re describing memorable, so creating a clear person or avatar to represent them will be more effective than making abstract generalizations about a demographic.
All of these suggestions are focused on making your articles look nice. Sadly, no one notices if your writing looks nice. They just notice if it looks sloppy. So I suppose we could say this section is more about making sure you don’t look sloppy.
This is also primarily about writing on the Internet. Some of these rules won’t apply to other areas like book writing or academic writing.
Double spaces after periods is an old typewriter convention. Digital fonts have dynamic spacing, so there’s no reason to create extra space-emphasis at the end of a sentence. It’ll look odd to anyone used to reading on a computer, and makes you come off as old and academic.
See how skimmable this article is with the hierarchy of headers? It helps new readers keep their bearings as they move through the article, and it helps return readers find the information they’re looking for. It also makes the article less intimidating. No one wants to try to slog through a wall of text when they could be looking at dog videos on Instagram.
The Internet isn’t your English 101 class. You shouldn’t be writing 8-10 sentence paragraphs unless you have an important point that needs the extra meat.
Keep your paragraphs to five sentences or shorter. It will make your article less intimidating, make it more skimmable, and help you avoid spending more time than necessary on any one point.
And when you do write a long paragraph, it’ll stand out and be seen as more important. Save the length for when you need it.
There’s nothing wrong with writing a long article, so long as you have a reason for its length. Don’t set an arbitrary word count you’re aiming for. Write until you’ve done the topic justice. If it can be done in 500 words, great. If it takes 4,000, that’s fine too. The most important factor is whether you’ve covered the topic in sufficient detail with sufficient brevity.
The easiest way to make your article look amateur and poorly formatted is to allow inconsistency to creep in. These are subtle, and you might miss them if you haven’t practiced looking for them, so you’ll have to resolve to keep a close eye out for any inconsistencies you can fix either in what you’ve written or in how it appears on your site.
Some typical sources of inconsistency are:
The last important rule is to ignore the rules occasionally. Sometimes an adverb sounds great. Sometimes you want to repeat words. Sometimes you want to use a bunch of short, or long, sentences.
By only following the rules 90% of the time, your deliberate decisions to break them will make your writing pop in a way uniquely yours. And as your writing style develops, you can add your own rules, remove ones you don’t agree with, and slowly refine what you believe is a good style for yourself.
Then consider joining the 25,000 other people getting the Monday Medley newsletter. It's a collection of fascinating finds from my week, usually about psychology, technology, health, philosophy, and whatever else catches my interest. I also include new articles and book notes.