Venkatesh Rao On Writing

The following is a condensed/adapted version of the writing advice shared by Venkatesh Rao on Quora. If you are not familiar with Rao’s work, do check out Ribbon Farm for some intellectually stimulating essays and writings.

What does it take to be an advanced writer?

Are you developing your writing skills or are you improving your thinking skills?

The two are the same things in the beginner stage, but differ in the advanced stage, even though the medium remains the same for both (words).

Advanced Writing Skills

• Recognise your natural talents and choose to either go with or against your grain.
• The ability to accurately measure how good you are, and how fast you are getting better.

Writers vs. Thinkers

Do you want to be a writer or a thinker? One lifetime normally isn’t enough to be both.

You have to choose.

The divide between thinkers and writers is more important than one between fiction and non-fiction writers.

You could divide the world of advanced writers into a 2x2, based on whether they are prioritising developing their thinking or their writing, and whether they are focusing on fiction or non-fiction.

J. K. Rowling is a thinking-first fiction writer. David Foster Wallace was a writing-first fiction writer.

V. Rao calls himself a decent thinking-first non-fiction writer. Marc Levinson, the author of The Box is a good example of a really good thinking-first non-fiction writer.

The fourth quadrant is rather empty, since there aren’t many writing-first nonfiction writers. (Writing to think). Many academic analytical philosophers qualify, but their writing is not generally read by ordinary people.

Many people can have a decent pastiche of JKR. Once the plot and characters are thoughts out, you follow it up with writing, in iterations to improve.

It is difficult to emulate DFW’s skill as a writer.

Many bloggers think better than DFW. He is not that great of a thinker.

How Good Are You?

• The ability to accurately measure how good you are, and how fast you are getting better.
• Readers’ comments help you measure popularity of the things you write about, but aren’t much help in understanding your own skill levels.
• Only advanced writers can tell the difference between the good and the best.
• Not even very good editors who don’t themselves write can tell.
• It’s because your measurement systems themselves improve mainly with writing. Reading alone won’t do.

How to go about this?

• Triangulate your skill from two directions.
  • Sensitise yourself to good writing.
    • Artists look at art differently compared to non-artists
    • It is harder to measure, but writers read differently.
    • “reading like a writer” by Francine Prose (book to read).
  • Learn to assess your own progress
    • Having other writers react to your work is part of it, but since writers (outside of genres) have very different interests, this is of limited value.
    • You need to develop an inner sense of how good you are.

What makes this so hard?

• As you evolve as a writer you increasingly become blind to your own style,
• It may be obvious to others that you overuse certain words for example. “It will not be obvious to you.”

How to measure yourself better?

• You need an indirect and objective measure. The secret lies in a single word I have already used. Any guesses which one?

• 10,000 Hours in writing

  • A prolific writer can usually churn out about 1000 reasonably decent words in an hour, so if you count in words, it might seem like 10 million words would be enough. Or at 4 hours a day, 250 days a year, about 10 years.
  • Any idiot can clock 10 years in words even with casual writing
  • What matters is not how much you write, but how much you rewrite.

“Rewrite” is the magic word (actually it is my shorthand for “read aloud and rewrite”. Reading aloud vastly increases the effectiveness of your rewriting).

The HUGE difference between everyday writing that everybody does and serious writing is the proportion that is re-writing. I’d estimate that for non-writers, rewriting accounts for maybe 10-20% of their writing.

For serious writers, it accounts for anywhere between 50-90% depending on how critical the particular piece is.

I write for free but charge for eliminating words.

When you hit 10,000 hours of rewriting, you’ll be a skilled writer or a skilled thinker with the written word. If you want to be both, it’ll take you 20,000 hours.

What makes Shakespeare special?

• Because he was an exceptional writer and thinker
• You need to spend 2000-3000 hours merely to appreciate how spectacularly good he was at both.
• In fact one of my litmus tests for whether you have advanced writing skills is whether you can write an interesting and original and personal essay discussing why you like 4-5 of your favorite Shakespeare verses.

An example of a modern writer who achieves a Shakespeare-like writing/thinking balance is Paul Graham.

Two kinds of rewrites.

• Rewrites that help you become a better thinker
• Rewrites that help you become a better writer.

How Good a Rewriter Are You?

• Test to see if you can rewrite at all.
  • Take a good passage of about 1000 words that you’ve written (and are reasonably happy with) and Start rewriting
  • Keep going until you are down to thinking about one last teeny decision.
  • If you hit comma-level diminishing marginal improvements in less than 4-5 hours, you are not an advanced writer.

Assuming you do care about your skills and the ideas/story the passage was about, if you can’t sustain 4-5 hours of rewriting (remember, this is about 4000-5000 words of first-dump writing), it means you can’t see potential areas for improvements and/or don’t know how to execute those improvements.

It’s actually what I call “first-dump writing” that is tedious brainless grunt-work (though as you improve, your first-dump quality will improve as well, and eventually you will be able to hit magazine quality at first dump. And on occasion, serious inspiration will strike, and a piece of writing will be born first-dump perfect).

• Rewriting takes skill. (and time)
  • If you merely schedule 5 hours to do rewriting work on a 1000 word piece, and don’t have the skills to fill those 5 hours, you cannot log them.
  • When you are starting out on your 10,000 hours of deliberate practice, you will initially only be able to achieve about 10% rewriting. As you improve, so will your rewrite capacity.

I estimate that it will take a serious writer about 20 years to hit 10,000 rewrite hours at an average pace. If you start at age 13 (a typical age for discovering a love for writing) and go like crazy, you could be a skilled writer/word-thinker in 10 years. So yeah, you can “arrive” as young as age 23.

The Two Types of Rewrites

• some of your rewriting was about the ideas (including/excluding ideas, compressing them, clarifying them) Thinker Re-writes : Accuracy of the content

• some of it was about the language (word choice, sentence structure, paragraph breaks…) Writer Re-writes : Precision with which your express the ideas

• At typing level you cannot see them apart. It is a subconscious mix.

• But at the deliberate learning level, you can.

• To become a better word-thinker, you have to constantly be reading (reading like a writer, in the sense of Francine Prose) about more complicated ideas from different domains and even other media.

• Programming and math can help, as can visual thinking.

• You should constantly be picking up intellectual tricks, clever metaphors and frames, interesting ways of dissolving dichotomies, subtle rhetorical devices.

For becoming a better word-thinker read his book Tempo: timing, tactics and strategy in narrative-driven decision-making

So let me elaborate on what I have seen of the path I have not taken, to the extent that I can see ahead from the fork in the road.

Writer Rewrites

To become a better writer, you have to read people with a much better ear for language itself.

• Great fiction, poetry and some very precise kinds of philosophical writing are what you need to consume.
• Screeplays and plays are great too.
• The key here is that all these types of writing impose severe constraints on form, so it makes sense that to work with these types, you have to improve your formal precision with language.

There are two main sub-skills:

• Semantic precision
• Grammatical precision.

Semantic precision is easiest to see at the word level.

• When I read a DFW passage, it is like looking at a pinprick-sharp photograph, compared to my own blurry photographs.
• He unerringly picks words to use that simply work 100x better than my choices.
• It’s like he has a 15 megapixel camera and a tripod, while I am using a 3 megapixel point-and-shoot.
• A bigger vocabulary isn’t enough.
• The skill lies in matching words to needs.

And this isn’t just at the word level. His sentences, paragraphs and chapters are massively preciseas well.

James Joyce is another example. His prose has been described as having the precision of poetry (an amazing feat, given that typical good poetry is generally 100x more precise than typical good prose, and Ulysees is HUGE).

Grammatical precision isn’t about knowing the rules.

• It is about knowing what to do where there are no rules.
• It is an instinctive sense of evolutionary direction in your chosen language and being ahead of the curve with respect to the Grammar Nazis.
• They codify, legitimize and enforce the rules you make up.
• Great writers don’t just push the boundaries of language and get away with it. They actually move the language itself and create and destroy jobs in the Grammar Nazi labor market.