Classic prose: a window onto the world

We can think of writing as a conversation between the writer and the reader. Conversations come in different styles. Some are didactic: one person knows more than the other person, and is telling that person how it is. Some are collaborative: both parties are trying to build something together. Some are funny, some are serious. Some are aimed at an answer, some are just for fun.

Cognitive scientist and prolific writer Steven Pinker describes the conversational metaphor that underlies what he calls “classic prose”. In this style of writing, the writer is helping the reader to see some part of the world. “The writer can see something that the reader has not yet noticed, and he orients the reader’s gaze so that she can see it for herself.” The writer is disinterestedly presenting the truth. — simply showing how the world is. The writer already knows how the world is — and “he is not using the occasion of writing to sort out what he thinks.”

“In classic style the writer has worked hard to find something worth showing and the perfect vantage point from which to see it. The reader may have to work hard to discern it, but her efforts will be rewarded.”

“Nor does the writer of classic prose have to argue for the truth; he just needs to present it. That is because the reader is competent and can recognize the truth when she sees it, as long as she is given an unobstructed view.”

“The writer and the reader are equals, and the process of directing the reader’s gaze takes the form of a conversation.”

Quotes from Pinker’s book The Sense of Style. Pinker credits the articulation of classic prose to literary scholars Francis-Noël Thomas and Mark Turner, in their book Clear and Simple as the Truth.

Writing is knowing your conversation

When we converse with a partner in real life, we have a sense of what they know, what they’re interested in, and how they’re feeling. We see their nods of understanding and their eyebrow-raises of surprise. We read their boredom by their lack of response or the wandering of their eyes. If they are confused or incredulous, they are free to stop us and request clarification.

When we write, we enjoy none of these contextual clues and real-time responses. The reader is remote from the writer: invisible, silent. Distant in time and space.

But in order to engage our reader, we must transmit a stream of words that will keep the reader engaged and not bored or incredulous. It’s the same job as we have real life. We must understand what the reader knows, believes, feels, and wants so that we can keep them engaged as we lay down the next thought to move the reader’s mind in the direction we want it to go.

To do this, we must have a clear conception of the type of imaginary conversation we are in with the reader. There are many possibilities. We may imagine ourselves as a preacher delivering a sermon. We may be a subject matter expert explaining a topic to an interested friend.

Whatever the case, the writer must imagine himself in some kind of conversation speak as he would in the successful real-life version of the conversation.

Which simulation should a writer immerse himself in? In another post I’ll tell you about the classic style.

The above is a paraphrase from chapter 2 of Steven Pinker’s “The Sense of Style”.

The “Winds of Winter” was great

Warning: spoilers

The Game of Thrones season 6 finale “The Winds of Winter” was satisfying. Let me count the satisfactions.

  1. The opening scenes of Cersei, Tommen, the High Sparrow and others donning their attire. Yeah. Shit is about to go down.
  2. Walder Frey going about being the lecherous old freak that he is, when bam! Arya Stark makes him eat his kids and cuts his throat!
  3. Cersei just says fuck it and blows everyone up!
  4. Jon Snow and Sansa sitting atop the wall in Winterfell felt so right.
  5. Old Lady Tyrell giving those Dornish sisters what’s what.
  6. That little Mormont girl calling all those big Northern dudes out for not heeding the call.
  7. All those big Northern dudes a minute later: “Da King in da Norf!”
  8. That flashback at the end: whoooaaa, so Jon Snow is Jon Targaryen? Such intrigue. Will he get it on with Sansa? I guess she’s still his half-sister. Or what about with Daenerys? But now she’s his… aunt? But if he’s not a Stark by paternal lineage, what about this newly-refangled Northern alliance?

If I had the data on every television episode I’ve ever watched in terms of satisfaction per minute, I bet this would be in the top 5.

All I’ve ever learned from love is how to shoot somebody who outdrew you


You see a warning sign. You withdraw. She sees you withdraw. You see her seeing you withdraw. You shoot her in the face. Metaphorically.

All of this to keep yourself safe. When avoiding vulnerability may not be so safe.

3 reasons style matters in your writing

According to Steven Pinker in “The Sense of Style”.


It ensures that writers will get their messages across.


Style earns trust. If readers can see that a writer cares about consistency and accuracy in her prose, they will be reassured that the writer cares about those virtues in conduct they cannot see as easily. Here is how one technology executive explains why he rejects job applications filled with errors of grammar and punctuation: “If it takes someone more than 20 years to notice how to properly use it’s, then that’s not a learning curve I’m comfortable with.”


Style, not least, adds beauty to the world. To a literate reader, a crisp sentence, an arresting metaphor, a witty aside, an elegant turn of phrase are among life’s greatest pleasures. And as we shall see in the first chapter, this thoroughly impractical virtue of good writing is where the practical effort of mastering good writing must begin.

The onion model of risk: a framework for addressing risk in a startup

You’re developing a new product. This is an innovation play, not an optimization one. That means you’re plopping down in an area of solution space where you don’t know how to move in order to succeed. There’s a ton of risk. There are lots of ways this could fail.

Your goal is not to fail quickly. Your goal is to succeed. Short of that, you want to know that you’re not going to succeed as quickly as possible so that you can stop.

What you want to do is systemize your risks, and attack them one by one. To do that, use the onion model.

This comes from Marc Andreessen, who says he got it from Andy Rachleff.

If you’re an investor, you look at the risk around an investment as if it’s an onion. Just like you peel an onion and remove each layer in turn, risk in a startup investment comes in layers that get peeled away — reduced — one by one.

Here are the risks Andreessen lists:

Founder risk — does the startup have the right founding team? A common founding team might include a great technologist, plus someone who can run the company, at least to start. Is the technologist really all that? Is the business person capable of running the company? Is the business person missing from the team altogether? Is it a business person or business people with no technologist, and therefore virtually unfundable?

Market risk — is there a market for the product (using the term product and service interchangeably)? Will anyone want it? Will they pay for it? How much will they pay? How do we know?

Competition risk — are there too many other startups already doing this? Is this startup sufficiently differentiated from the other startups, and also differentiated from any large incumbents?

Timing risk — is it too early? Is it too late?

Financing risk — after we invest in this round, how many additional rounds of financing will be required for the company to become profitable, and what will the dollar total be? How certain are we about these estimates? How do we know?

Marketing risk — will this startup be able to cut through the noise? How much will marketing cost? Do the economics of customer acquisition — the cost to acquire a customer, and the revenue that customer will generate — work?

Distribution risk — does this startup need certain distribution partners to succeed? Will it be able to get them? How? (For example, this is a common problem with mobile startups that need deals with major mobile carriers to succeed.)

Technology risk — can the product be built? Does it involve rocket science — or an equivalent, like artificial intelligence or natural language processing? Are there fundamental breakthroughs that need to happen? If so, how certain are we that they will happen, or that this team will be able to make them?

Product risk — even assuming the product can in theory be built, can this team build it?

Hiring risk — what positions does the startup need to hire for in order to execute its plan? E.g. a startup planning to build a high-scale web service will need a VP of Operations — will the founding team be able to hire a good one?

Location risk — where is the startup located? Can it hire the right talent in that location? And will I as the VC need to drive more than 20 minutes in my Mercedes SLR McLaren to get there?

He also talks about it in this lecture.

How to give feedback: a framework for managers

The following is a framework presented by Kim Scott.

Helpful for: Managers who want to give valuable feedback to their reports.

Background: Guidance (a more humane term for feedback) is, in Kim Scott’s opinion, the single most important part of managing people.

Example: Kim had recently joined Google and was about to give a presentation to senior leaders on how the Adsense business was doing. It was an important meeting for her. The meeting went okay, Kim thought, because Adsense was crushing it, and that was what she told them.

After the meeting, Kim’s boss was giving her feedback — a bunch of positive things that gave the impression a “but” was coming. And there was: Kim’s manager said, “But, you said “um” a lot.”

Kim was relieved. So what, she said. The meeting went well.

Her manager tried again to show her that the “um”s were a problem, but Kim again brushed it off, saying, “I’m just really busy; it just doesn’t seem like the most important thing.”

“Kim, I can tell I’m not getting through to you here,” her boss said. “I’m going to have to be more clear. When you say “um” every third word, it makes you sound stupid.”

That got Kim’s attention.

This comment may seem unkind, but Kim thinks it was the kindest thing her boss could have done. If her boss hadn’t said it just that way, she would have continued to brush it off, and would never have fixed the problem.

Framework: Vertical axis is the “give a damn” axis. Do you care personally about your report?

Horizontal axis is the “be willing to piss people off” axis. Our parents taught us that if you don’t have anything nice to say, you shouldn’t say anything at all. But Kim would argue it’s your job — indeed, your moral obligation — to say it.

Read more at the First Round Review.

Should you delegate or do it yourself? A framework to help you decide

The following is a framework presented in a lecture by Keith Rabois in Sam Altman’s ‘How to Start a Startup’ lecture series at Stanford. This is a paraphrase of his talk.

Paraphrasing from Keith Rabois:

Question: Should I delegate this or do it myself?

Who’s this for: People in a management role.

When to use it: When trying to decide whether to delegate some task.

Background: To use the roles of writers and editors as a metaphor, editors are not writing most of the content in any publication. The same is true of your company: you shouldn’t be doing most of the work. And the way you get out of most of the work is to delegate.

Now the problem with delegating is that as the CEO or founder, you are actually responsible for everything. There is no excuse if things don’t go well. So how do you both delegate but not abdicate? It’s a pretty tricky challenge because both are sins: to abdicate, or to micromanage.

Framework: How do you decide whether to delegate it or do it yourself? Use this two by two matrix.

You basically sort your own level of conviction about a decision on a grate, extremely high or extremely low. There’s times when you know something is a mistake and there’s times when you wouldn’t really do it that way but you have no idea whether it’s the right or wrong answer. And then there is a consequence dimension. There are things that if you make the wrong decision are very catastrophic to your company and you will fail. There are things that are pretty low impact. At the end of the day they aren’t really going to make a big difference, at least initially.

So what I basically believe is where there is low consequence and you have very low confidence in your own opinion, you should absolutely delegate. And delegate completely, let people make mistakes and learn. On the other side, obviously where the consequences are dramatic and you have extremely high conviction that you are right, you actually can’t let your junior colleague make a mistake. You’re ultimately responsible for that mistake and it’s really important. You just can’t allow that to happen.

Example: An example of this is at Square, one of my favorite people in the world and my second hire, first marketing hire, had this program he wanted to run called Inner Square which allowed Square merchants to give out, imagine a food truck outside put out ten Squares on the counter and people could just grab them. And Kyle had this great idea that this would be an awesome marketing program. Squares would spread Squares to other people and to some extent it was on brand. So it didn’t have catastrophic consequences. Each of these ten Squares didn’t cost that much money, so financially we could afford to do it. But at that time, my ten years of experience said it was not going to work on a meaningful enough scale for our metrics and I preferred not to do it. Kyle was so excited about this that I decided to just let him do it. He learned that when you measure this thing, it’s not massive. It doesn’t create massive value for the company. It did require a fair amount of operational complexity to ship all these Squares to people and figure out how to get them, etc, etc. But it allowed him to be excited about his job and to learn how to filter future ideas. So it was totally worth letting him make the “mistake”.

Eradicating mosquitoes would be ecologically fine

According to a 2010 Nature article, total mosquito genocide might not cause any large problems.

Yet in many cases, scientists acknowledge that the ecological scar left by a missing mosquito would heal quickly as the niche was filled by other organisms. Life would continue as before — or even better. When it comes to the major disease vectors, “it’s difficult to see what the downside would be to removal, except for collateral damage”, says insect ecologist Steven Juliano, of Illinois State University in Normal. A world without mosquitoes would be “more secure for us”, says medical entomologist Carlos Brisola Marcondes from the Federal University of Santa Catarina in Brazil. “The elimination of Anopheles would be very significant for mankind.”

Why you should write in the morning

The first question is whether you really want to write. Not like ‘all else being equal’, like if time was free. But given the actual costs and opportunity costs.

If that answer is yes, then here’s the case for writing in the morning.

You cannot guarantee what will happen after you leave the house. After you start checking email. After work. After you get ready for bed.

But first thing in the morning, that’s your time.

Growing skill and achieving success is about practice. And for something like writing, getting practice is about building the habit. Only with habit will you do it frequently enough, over a long enough time, that you’ll build the skill.

That’s the number one thing for writing.

If you want to write, if it’s true that writing is the most important thing, the thing you want to do, then do it first. Do it when you wake up in the morning, or as soon as humanly possible thereafter.

Why not write in the evenings? Because at that point, it’s too easy to push it back. Until eventually, the trade off you’re making is between sleep and writing. That’s not a place you want to get yourself.

Why not schedule time during the day? Because stuff will come up.

Also, your energy is highest in the morning.

Minimize the number of variable items between the moment you wake up and writing. You can do routine, and habitual things where writing becomes one in the chain. But minimize the variable things. Don’t check your email first. Don’t do a phone call. Try not to see people, if you can prevent it. They’re unpredictable.