On What Makes Writing Work
Writing well is harder than it seems. When I transitioned from writing notes and thoughts to blog post and articles, I thought a lot more about my writing approach. When is this piece finished? Does it make a point? Does it have to make a point? Am I satisfied with it? Does it have that special something that makes reading satisfying? What is that special something? As I thought about these questions in my own writing, I kept referring back to writing approaches I’d encountered over the years, and noticed how some are entirely different and even contradictory to each other. So how do I go about answering these questions? Here are some of my favorite approaches.
A Game of Thrones Approach
George R.R. Martin is a great writer. Perhaps it’s the years spent editing his books, which drive his fans crazy. From the standpoint of writing fantasy and fictionalized political history, Martin was inspired by many sources from the War of the Roses to Tolkien, Marvel Comics to Medieval history. When reading the books of A Song of Ice and Fire (typically referred to by the first book, A Game of Thrones), his style stands out dramatically. Short chapters, told from characters’ points of view, with unreliable narration, and critically, that end with a cliffhanger.
When I read him, it’s the last point that stands out. I’ve never read so many cliffhangers. Martin draws you in by making sure that the end of every chapter leaves you wanting more. There is a close connection between one chapter and the next, or another several chapters away, which keeps you not only reading but engrossed. When you see a character, you’re more likely committed to see what happens to them later. With short chapters, each one can follow a character on a small arc, providing great character development as Martin explores their points of view and thought processes. The chapter focuses on details and minutiae, while revealing elements that affect other chapters and advancing the overall story. This is great storytelling.
Many writers have used the constant cliffhanger strategy successfully but Martin really perfected it in A Game of Thrones.
A Swim in a Pond in the Rain Approach
George Saunders is a writer and professor of creative writing at Syracuse University. He’s known for teaching a master class on short story writing that’s taken by many professional writers. The class focuses on a close reading of four Russian short story masters: Gogol, Tolstoy, Checkhov, and Turgenov. They read these writers to understand how great writing works, how short stories work, the craft behind them, and how they can be elevated into artistic masterpieces.
After teaching the class for decades, Saunders decided to turn it into a book and make it available to a general audience. Even better, there is an audiobook version in which professional actors (that you know and love) read the stories, which are interspersed with Saunders himself providing analysis. Short story writing is not an area I knew a lot about prior to this book, but it is hard for me to think of any book of any kind that I would recommend more. It’s called A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life, after a story by Chekhov.
In the first story, Checkhov’s “The Cart”, Saunders has the reader, the Cosby Show’s Phylicia Rashad, read just the first sentence of the story, then provides a few minutes of analysis. She then reads a few more sentences, and he interrupts again for another few minutes. This is the most extreme and intermittent analysis in the book, but it is supremely instructive.
The story begins “At half-past eight they drove out of the town.” Saunders asks, at this point we know very little, but if we only had this sentence, what would we know? Who is it that drove out of town? What did they drive in? What town was it? What were they doing in the town? Which half past eight was it and why were they leaving just then?
Some of these questions may be answered in the story to come after this first sentence. Some may be left to linger to lure the reader into continuing the story. But the real magic is Saunders’ revelation that to write this story required answering the same questions, which is the process that these great authors went through. These stories were not planned out and executed, they were discovered, and that is what turns short story writing into art.
I vaguely remember a short film I saw decades ago in which Nick Nolte played a famous aging artist trying to teach a younger aspiring student who he was also in a relationship with. She is struggling and expresses frustration and he distractedly tries to encourage her. But all the while he is obsessed. He sees through her. He can’t let go of his own work. In one scene, she’s speaking to him and he’s half listening while he obsessively and rapidly abuses a canvas, barely paying attention to her. If you’re a real artist, you have no choice.
Nothing has opened my eyes more to how great writing works, at least when it is being produced by four Russian masters. I didn’t realize this type of writing was possible, but knowing that it is changes my appreciation for this type of great writing.
The Amor Towles Approach
On the flipside of that artistry, you have Amor Towles. Towles went to Yale and then received an MA in English from Stanford, but he then became an investment banker. Only at the age of 47, did he publish his first novel, the Rules of Civility. I haven’t read it, but it received pretty good reviews. It was successful enough that he quit investment banking and became a novelist. His second novel, which I did read, is A Gentleman in Moscow. It’s about a Russian aristocrat who lives through the revolution and is spared because of a poem he writes in which he praises communism. They let him live out his life in a hotel in Moscow, and he observes decades of Russian history in that hotel. It’s a great book and I thoroughly enjoyed it.
I listened to an interview with Towles on the Econtalk podcast with Russ Roberts. Towles talks about his history but also about how he writes. What immediately caught my attention, after learning so much from Saunders’ book, is how diametrically opposite Towles writing style is. Towles is a planner. Before he writes, he sketches out outlines of all the characters and all their relationships and plot events. He maps out the entire book before he writes.
Towles is no Russian master but A Gentleman in Moscow was a great novel and highly acclaimed. It’s clearly great writing, great plotting and a great story. But is it art? Does it matter?
The Zettlekasten Approach
In the note taking world (yes, there is a note taking world and it is filled with rabid enthusiasts) there is a concept called Zettlekasten. Zettlekasten means “slip box” in German. It is often attributed to German sociologist Niklas Luhmann, a man who worked in the civil service for a decade before leaving to pursue a dream as an academic sociologist. He started writing on academic subjects and finally, at the age of 42, he became a professor at the University of Frankfurt. Luhmann was famously prolific, authoring more than 70 books and over 400 scholarly articles in his career, which he only started in his late 30s. When asked about his incredible productivity Luhmann admitted to being incredibly lazy. He attributed his productivity to the Zettlekasten, his note taking system. He didn’t invent the Zettlekasten, but certainly popularized it. There is a great book called How to Take Smart Notes which describes Luhmann, the Zettlekasten, and how to use it in a modern way.
Zettlekasten is a note taking system that uses “slips” or index cards more commonly, with small bits of information on each, linked to other notes with tags and metadata. Luhmann accumulated over 90,000 index cards in his Zettlekasten. The cards are stored in a box and reviewed periodically, elaborating notes into more developed writing, while discarding shorter ones. The longer writing is then itself reviewed and elaborated or discarded. Today this is all done digitally of course, and there are great systems like Obsidian, Logseq, and Roam that mimic this system to some degree and use some of the same principles.
The beauty of this system, according to Luhmann, is that when you have inspiration, you write a note. It’s not necessary to write out an entire article or paper, to worry about the style or editing of a piece. Rather, the insight is captured in its pure form, and later can be elaborated on. The result is a series of elaborated insights in a partially developed form. Crucially, these insights are linked to one another. When Luhmann wanted to write a piece on some subject, he’d look up the tag associated with that subject, and find a variety of linked insights, already developed. He didn’t have to sit down and think of a thesis and start writing an article, faced with a blank sheet of paper. Instead, he already had an outline and much of the writing done. All he had to do was connect the insights and fill in the gaps. To achieve this, instead of occasionally writing a piece which required more effort and concentration, he would consistently and daily read and write short insights, collect them, and work them through the Zettlekasten. Thus he could be “lazy” and yet achieve remarkable levels of productivity.
This system works particularly well for academic writing, but its also been used for fiction. Its advantage is that it allows a writer to focus on the writing apart from the content, by making the latter easier to generate consistently. It has produced a lot of work, but does it produce great writing?
The Zinger Approach
In the past few years, since I’ve been primarily an investor at Akili, I’ve been reading a lot of investment books. The most recent one, also one of my favorites, is Pulak Prasad’s What I Learned About Investing From Darwin. Prasad is the founder of Nalanda Capital, a Singapore based fund that invests primarily in Indian public equities.
Like many investors, Prasad had his investment awakening by discovering the great Warren Buffett, and through him, the evolution of value investing. Prasad adapted his own version of value investing, which he describes in the book. What he noticed is that much of his version has analogues in evolutionary theory, and there are many examples in nature, all which Darwin describes and Prasad quotes, that help explain deep principles that underlie the success of his strategies.
For an investment book, it’s extremely useful to consistently use analogies, examples, and particularly humor, otherwise you might make your audience fall asleep (at the wheel in my case, I listened to the audiobook). This is a style of writing that I see often, particularly in certain kinds of books for the general public. Every chapter, sometimes every section of every chapter, ends in a joke, a punchline, an insightful question. A zinger. The zinger keeps you wanting more. It makes you laugh. It makes you think. And it makes you want to read on. The zinger approach is like the cliffhanger approach of A Game of Thrones, but rather than being directly related to the plot of a novel, it’s often used in nonfiction, and just provides a satisfying conclusion that leaves you feeling good and wanting more of that feeling. Prasad does a great job at this. It’s not easy, but it’s very satisfying to consistently provide zingers to keep your readers hearts and minds engaged.
The Meandering But Enthusiastic High Intellectual Approach
One of my favorite writers was David Graeber. I say was because Graeber tragically died in Venice in 2020 of necrotic pancreatitis, probably related to COVID. He was 59. Graeber was an anarchist, a radical, and an anthropologist by training. He studied with one of the great anthropologists, University of Chicago’s Marshall Sahlins. He was fired from Yale, allegedly for his political views, and was one of the core organizers of Occupy Wall Street.
Graeber’s first major book was *Debt: The first 5,000 years.* It is an economic history, told from an anthropological (and sometimes archaeological) perspective. It is a vast book with so many interesting threads that lead to other rabbit holes of research. It’s very difficult to put down which is unusual for a 544 page book on economic history. I attribute it to Graeber’s enthusiasm for his subject, for uncovering interesting ideas and alternative theories. Whether many of these are true is disputed, but the exploration is fascinating and I learned many things from it. Such as…
The importance of reputation in the golden age of Islamic maritime trade (I wrote a patent related to reputation systems so I was delighted to learn more about them historically). The primacy of credit over currency in the history of financial transactions. And his most contrarian claim (at least with respect to economic textbooks), the complete myth of the barter system as the precursor to money.
After Debt, Graeber wrote a series of books and articles, some of which captured the cultural zeitgeist and have since become memes. On such example from an article that captured enough attention for him to turn it into a book is Bullshit Jobs, in which he argues that “Huge swathes of people, in Europe and North America in particular, spend their entire working lives performing tasks they secretly believe do not really need to be performed.” He also wrote a criminally underappreciated and very funny book about bureaucracy called The Utopia of Rules, with a hilarious chapter about Batman.
Debt, credit, jobs, bureaucracy. These are not exactly the most riveting subjects, so how does Graeber make them so interesting?
This is not exclusive to Graeber, but I mention him because I’ve noticed a pattern where sometimes highly intellectual subjects are written in a manner that doesn’t follow any of the approaches I’ve mentioned. There is no zinger, no lead, no cliffhanger, there doesn’t appear to be any grand outline or structure, and there certainly is no inspirational exploration that turns into fine art. Rather, it is more of a meandering from one subject to another, loosely connected. Like a David Foster Wallace novel that goes on tangents into random subjects and treats each of those not as a sidenote (though they are usually footnotes), but with paragraphs and sometimes pages of exposition and reflection on subjects that would sometimes take up more space than the actual narrative.
In both cases, Graeber and Wallace were super smart, articulate, and enjoyed weaving humor, irony, and a sense of absurdity into both highly intellectual and highly mundane subjects, and sometimes finding the intellectual in the mundane itself. But you could tell for both of them, they did not slog through their writing, they were so at home and delighted that, to quote Warren Buffett, they were “tap dancing to work.”
On Writing Well Approach
From every example I’ve encountered, maybe the best resource for writing well and understanding how writing works and how to make it work, there is nothing better than On Writing Well by William Zinsser.
Zinsser is a writer’s writer. A journalist, a mostly nonfiction author, and a teacher of writing at Yale, Columbia, and the New School. In the book, Zinsser writes on and illustrates perfectly the lessons and wisdom of a life spent focused on the craft. His prose is incredible. You can feel it when you read him. His pace, his rhythm, his playful attitude towards the reader. You feel like you’re getting to know him as you read. And that, is great writing.
On the experience of writing itself, he opened my eyes to the joy and the slog of it. Of rewriting. Of editing. These become clear only when you understand how much is possible, and how much work it takes to achieve it. It is an art that only a true Zen master could perfect. It’s like quietly and methodically trimming an endless bonsai tree. It is a Sisyphean task.
Just as there is no right way to build a business, there is no right way to write, as I hope is clear from the subject of this piece. Yet there are rules and principles in writing that are fairly universal. They are well known, simple, and finite. Here are a few:
Usage
Why is one word good and another word cheap? I can’t give you an answer, because usage has no fixed boundaries. Language is a fabric that changes from one week to another, adding new strands and dropping old ones…
Words
…these dreary phrases constitute writing at its most banal. We know just what to expect. No surprise awaits us in the form of an unusual word, an oblique look. We are in the hands of a hack, and we know it right away. We stop reading. Don’t let yourself get in this position. The only way to avoid it is to care deeply about words.
The Audience
You are writing for yourself…and if you go about it with enjoyment you will also entertain the readers who are worth writing for. If you lose the dullards back in the dust, you don’t want them anyway.
Style
This is the problem of writers who set out deliberately to garnish their prose. You lose whatever it is that makes you unique. The reader will notice if you are putting on airs. Readers want the person who is talking to them to sound genuine… Sell yourself, and your subject will exert its own appeal.
Clutter
Writing improves in direct ratio to the number of things we can keep out of it that shouldn’t be there… Examine every word you put on paper. You’ll find a surprising number that don’t serve any purpose.
Simplicity
But the secret of good writing is to strip every sentence to its cleanest components. Every word that serves no function, every long word that could be a short word, every adverb that carries the same meaning that’s already in the verb, every passive construction that leaves the reader unsure of who is doing what — these are the thousand and one adulterants that weaken the strength of a sentence.
The Transaction
Ultimately the product that any writer has to sell is not the subject being written about, but who he or she is… What holds me is the enthusiasm of the writer for his field…Good writing has an aliveness that keeps the reader reading from one paragraph to the next…
So after all these writing approaches, what do I leave you with? Only this. Writing is thinking. I try to think clearly, and let my writing reflect that. I hope you will too.
Thanks for reading.