Thoughts on Writing

(I wrote this years ago and originally published it on my internal Amazon blog.   I’ve sent it to various folks over the years, but wanted to give it a permanent home on the internet.)

Why writing matters

Clear writing is clear thinking. Conversely, muddy writing implies muddy thinking. Your readers know this instinctively — clunky sentences and confused composition undermine your credibility. In the worst case your readers simply stop, rendering your effort wasted. If you’re not willing to write well, perhaps you shouldn’t bother writing at all.

Then there is the question of impact. If you want to accomplish something extraordinary in your life, Scott Adams suggests two strategies: 1) Become the best at one specific thing, or 2) become very good (top 25%) at two or more things. The first is difficult to the point of impossibility [1]. The second is remarkably easy.

Marc Andreessen picks up where Adams leaves off, suggesting five skills that in combination with your degree can dramatically increase your potential. The first of Andreessen’s five skills? Communication. Andreessen notes, “The great thing about communication is that most people are terrible at it, because they never take it seriously as a skill to develop.”

A skill like any other

The good news is that you learn to write well just like every other skill you’ve acquired in your life, through study and practice.

At the very least, read Strunk and White’s Elements of Style. It’s a thin book, you can read it in a couple hours. It reviews crucial bits of English grammar and punctuation and then goes on to outline some key principles of composition. Perhaps the most important these is that the paragraph is the unit of composition. Each idea you want to communicate should have a crisp paragraph dedicated to its development, and each paragraph should be dedicated to a single topic.

An excellent accompaniment to Strunk and White is a style guide from a publication you admire. I have both the Economist Style Guide and the New York Times Manual of Style. These are useful for looking up topics like use of the apostrophe, details of capitalization, the difference between affect and effect, and usage of that and which. Beyond useful, these guides are fun to flip through; if you enjoy surfing material like The Jargon File, you’ll also like the Economist Style Guide.

Finally, to help develop your own distinctive voice, read Zinssers’ On Writing Well. Zinnser stresses the importance of being present in your writing. Feel free to use the first person, ignoring any childhood warnings to the contrary — you’re not writing for a newspaper. Even in genres where ‘I’ and ‘we’ are discouraged, the reader should feel the presence of a unique author behind the text.

As for practice, opportunities abound. How many crappy emails do you write each week that would benefit from a more formal treatment? Take just one each week and give the topic the respect it deserves. The next time you present in front of a group, write a short paper detailing your thesis and hand it out to the audience. If you’re a developer, write a two or three page paper describing and defending your next design choice. The written word is the most precise, long-lasting mode of communication available. Use it.


Imagine a serious performer giving a dramatic reading. He strides purposefully onto the stage and takes his position facing the audience. The murmur of the crowd settles. The performer takes a breath to begin, and looses a huge fart. This performance is now in such trouble it may never recover.

Your opening sentence has to be perfect. Your opening paragraph has to be great. You can afford a sloppy sentence midway through — people might not even notice — but not at the beginning. So, spend an inordinate amount of time crafting your opening. It should be clear, tight and grammatically correct. Anything less is unacceptable.


After spelling and grammar, empathy is the most critical skill of a decent technical writer. You must be able to put yourself in your audience’s shoes and simulate their thought process, starting from an appropriate level of ignorance. Failure to accurately anticipate and answer the reader’s questions is the cause of most muddled writing.

If you lack this skill, a crutch is to build your document like you would a large mathematical proof, layering on successive, interlocking theorems (statements) and proofs (arguments or supporting evidence) that lead inevitably to your conclusion.


The easiest way to keep your readers engaged is to tell stories. Humans are intensely primed for stories; if you introduce a character and narrate a sequence of events, your audience will automatically follow along. Don’t believe me? Watch this. Actually, watch all four parts, Ira Glass is one of the greats.

The first critical element of story is tension and resolution. The simplest way to create tension in your writing is to pose questions: Will the wolf eat Little Red Riding Hood? Which design is the best? Will Cinderella get her just reward? When the latest release decreased efficiency, how will the problem be resolved?

Open up some space in the dry recitation of the facts. Leave your reader in doubt about the outcome for the beat between sentences, propelling them though the piece. The technique of introducing questions nests — leave a big question open for the duration of the piece, and along the way, continuously pose and then answer smaller questions. This is the essence of interesting writing.

The second critical part of story is character. Too often the characters in technical writing are abstract. The more human you can make them, the better. I am reminded of an example from Malcolm Gladwell’s The Tipping Point. Paraphrasing, suppose I create a deck of cards by combining two normal decks, one with red backs, the other with blue backs. I select only face cards from the red deck (discarding the rest), and combine them with all the cards from the blue deck. Then I shuffle them, turning some face up and others face down randomly, and deal out four cards:

  • a queen
  • a face down card with a blue back
  • a four
  • a face down card with a red back

Which cards do you need to turn over to determine whether I created the deck as described above? Many people will get the answer wrong, and those that get it right generally need to think carefully about their answer.

Now consider a similar problem. You manage a pool hall that serves beer, and is popular with students of a nearby college. One of your jobs is to make sure no one underage is drinking alcohol. One evening you see the following:

  • a man drinking a glass of soda
  • an elderly man whose glass you cannot see
  • a woman drinking a beer
  • a teenager whose glass you cannot see

What do you need to do to ensure that the law is being followed? Most people will get this right, and do it instantly. This is surprising because the two problems are logically identical.

You need to ID the woman drinking beer, and make sure the teenager isn’t drinking beer. Anyone can drink soda, and the elderly man can drink whatever he wants. Similarly, you need to flip over the four to make sure it’s from the blue deck, and the red card to make sure
it’s a face card. It doesn’t matter what is on the reverse of the other two cards: a queen can have either a red or blue back, blue card can be either a face card or not.

The difference between the problems is that one involves people. Human brains through both evolution and socialization are highly adapted for reasoning about people. Smart writers take advantage of this fact.

Instead of software systems, make the people who create and deploy them the subjects of your sentences. Talk in detail about the customers that will use those systems — what are their needs and how will those needs be met? The more human the actors in your writing, the more interesting it will be.


I spent much of my late-twenties studying art — modern dance in particular. Both watching and creating performances were valuable training for my professional life.

Art, in my opinion, is fundamentally about communicating (perhaps with only yourself), and artists think harder about effective communication than any other profession.

Studying art, artists, and particularly how artists think about their work has shaped my own aesthetic sense and informed my voice. I encourage you to find some aspect of the arts you enjoy and immerse yourself in it.

A great resource for learning about the inner thoughts of artists is Terry Gross’s Fresh Air Podcast. Regarded as one of the best interviewers of our time, she often has artists as guests. Memorable interviews include performers ranging from Steve Martin to Gene Hackman, musicians like Rob Halford of Judas Priest, writer Alan Ball of Six Feet Under and American Beauty, and poets like Billy Collins.


I deeply dislike the dull form of 1) tell them what you’re going to tell them, 2) tell them, and 3) tell them what you told them. If I thought I could accurately capture the ideas in the body of the text in fewer words, I would have done so. I am reminded of Robert Frost, who was once asked after a reading about the reason behind his choice to double the final line of Stopping by Woods on a Snowy Evening. His simple response?

And miles to go before I sleep,
And miles to go before I sleep.

Not helpful, you might complain, but accurate in its poetic way.

In truth, ending is an issue I still struggle with. I have little to say, so perhaps it is best to simply quote the final line of Paul Graham’s short piece on writing:

learn to recognize the approach of an ending, and when one appears, grab it.

[1] Worse than difficult, it usually requires a great deal of luck. A friend of mine plays for the Chicago Symphony Orchestra, widely considered one of the greatest orchestras in the world. I can almost guarantee that she has worked harder on her craft than you have on yours, but to land that gig she also needed luck.

She was one of perhaps two hundred people who auditioned for the spot. They were all tremendously talented, with technical mastery over the most difficult music of their instrument’s repertoire. But on that particular day, for whatever reason, the judges took a liking to my friend’s sound. Each judge heard something small, maybe tiny bit of technique gleaned from a old teacher, or a flicker of emotion shaped by a distant life experience. Whatever it was — and no one knows — those details made the difference.

Talent and hard work got her in the door, but the ineffable chemistry of a particular lifetime with her instrument is why she got the gig. The other 199 applicants? Take a hike. At her level, music is a cruel profession.


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