I just published a book and a friend, another book writer, privately complimented me on the "poetic grace" of my book. The comment made my day. So I'll take that as my claim to being an "medium advanced" writer.

But though I will offer some sincere tips here, I would never offer a writing class. Why? Because I am not trying to develop writing skills. I am trying to develop thinking skills.

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

So the first advanced writing skill is to recognize your natural talents and choose to either go with or against your grain.

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

Writers vs. Thinkers

You have to choose.

The divide between thinkers and writers is more important than the one between fiction and non-fiction writers. You could divide the world of advanced writers into a 2x2, based on whether they are prioritizing developing their thinking or their writing, and whether they are focusing on fiction or non-fiction.

My hypothesis (I haven't yet gotten to a stage where I can check this) is that it is easier to cross the fiction/non-fiction divide than it is to cross the writing-first/thinking first divide.

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

I am a decent thinking-first non-fiction writer. I'd say Marc Levinson, author of The Box is an 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. Many academic analytical philosophers qualify, but their writing is not generally read by ordinary people.

I think I could pull off a decent pastiche of JKR (many people can and have), though I primarily write non-fiction.

I have no hope in hell of ever getting to even 10% of DFW's skill as a writer. I'll explain why in a bit.

But as a thinker (based on his non-fiction pieces), I think I may already be better than him in some ways. Which isn't saying much, since as a thinker he was not very good actually. Many bloggers think better than him.

How Good Are You?

The first skill you need to develop as an "advanced" writer is the ability to accurately measure how good you are, and how fast you are getting better.

Readers' comments help you measure the popularity of the things you write about, but aren't much help in understanding your own skill levels, since they are simply not sensitive to writing skill beyond a certain level. They can tell beer apart from wine, but cannot tell varieties of wine apart.

Sounds snooty, but it is true. If I gave an average reader two of my sentences, one that I just shot off without much thought, and another that I rewrote a 100 times to get just right, most of them wouldn't be able to tell. But other serious writers can usually tell.

And actually only writers can tell. 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.

You have to triangulate your skill from two directions.

First, you have to sensitize yourself to good writing.

Studies show that artists look at art differently compared to non-artists (eyeball trackers show them looking at different things). This is what it means to "see" like an artist.

It is harder to measure, but writers read differently. The best exploration of (and instruction manual for) "reading like a writer" is the book of that name by Francine Prose. If you are a serious writer, buy and read that book now.

The second thing you have to do is 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.

This is hard because one of the things that happens as you evolve as a writer is that you increasingly become blind to your own style, or that you even have a style. To others it may be obvious that you overuse certain words for example. It will not be obvious to you.

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

Counting to 10,000 Hours

Writing is a skill like any other, and the famous 10,000 hour rule should apply, and it does, but not in the way you might assume. 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.

The problem is everybody writes. And yes, things like emails count. So any idiot can clock that many words in 10 years even if they only do a lot of casual/work email and texting. You don't even need to throw up verbal puke in a journal/blog regularly like many horrible wannabe writers do.

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).

And rewrite hours are far harder to log, as you will see if you try an exercise I will suggest in a minute.

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. This Quora answer is not very critical for me, so I'd say it'll hit 50% by the time I am done. There are single paragraphs in my book though that took 5 minutes to write down initially, and then cost me hours to whip into shape, so that's like 99% rewriting. For my for-pay work, I probably average about 75%. For my own blog, I am erratic. Some pieces hit book-like 99% levels. Other pieces are at 70%. I don't think I've ever hit more than 65% on Quora.

People often ask me how I am so prolific. To be blunt, that's so easy for me, it is not much harder than just breathing. But rewriting is hard. It is torture. Since one measure of rewriting progress is words eliminated, I often joke that I write for free but charge for eliminating words.

But rewriting is the only kind of writing that counts. If you aren't rewriting, you aren't developing as a writer.

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.

Like I said, one lifetime normally isn't enough. That's why so few people make it past that bar.

Shakespeare is one of them.

If you never understood why writers especially revere him, this is why. 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. I'd rate him at one milli-Shakespeare. Most people can't be measured on that scale because they are not balanced biathletes.

Back on earth, there are two kinds of rewrites. Rewrites that help you become a better thinker, and rewrites that help you become a better writer.

How Good a Rewriter Are You?

First, try a little 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 have at it.

Start rewriting.

Keep going until you are down to thinking about one last teeny decision, like a specific word choice or a decision about whether or not to remove a comma. Be as OCD about it as you can be.

How long did it take you to get there? 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.

I hope I helped you prove to yourself that rewriting is NOT tedious, brainless grunt-work. 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. 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

If you actually tried the exercise, you probably noticed that some of your rewriting was about the ideas (including/excluding ideas, compressing them, clarifying them) and that some of it was about the language (word choice, sentence structure, paragraph breaks...)

The first kind is thinker-rewrites. It is about the accuracy of the content with respect to the pre-verbal ideas you are trying to capture.

The second kind is writer-rewrites. It is about the precision with which you express the ideas.

At the level of typing you cannot tease 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. Things like that.

I won't say more about thinking-rewrites, since this question isn't about becoming a better word-thinker (my book IS about that, hint hint).

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.

The range of suitable input material is much narrower. You may pick up some decent thinking tricks even from a bad writer/thinker like Thomas Friedman (his success is more due to his boundless energy and enthusiasm), but you will pick up no writing tricks.

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 and 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.

In fact his language is so precise that it makes his writing almost too rich to read. I've never finished any of his novels because they are too rich for me. My brain can't handle it.

And this isn't just at the word level. His sentences, paragraphs and chapters are massively precise as 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.

I'll stop here. I haven't directly answered the question because tips aren't really what help at an advanced level. That's like giving a man fish when what is needed is a lesson in fishing. Hopefully this served that purpose.

Happy rewrites!