Writing Lessons for a Better Life

Writing is one of those things you’ll need to be decent at no matter what business you’re in. It’s also one of the hardest things to get decent at, since it’s 90% art, 10% illogical grammar rules. Novelist William Maughan said there are three rules to good writing. “Unfortunately no one knows what they are.”

But here are a few I’ve found helpful.

1. Make your point and get out of people’s way

Readers have no tolerance for rambling. Lose their attention for two seconds and they’re gone, clicked away to another page.

The best writers tend to use the fewest words possible. That doesn’t mean their writing is short, but every sentence is critical, every word necessary. Elmore Leonard, the novelist, summed this up when he advised writers to “leave out the parts readers tend to skip.”

It took me a while to realize that a reader who doesn’t finish what you wrote isn’t disrespecting your work. It’s a sign that you, the author, disrespected their time. When writing, I like to think of a reader over my shoulder constantly saying:

What’s your point?

Just tell me that point.

Then leave me alone.

Part of the reason this is hard is due to how writing is taught in school. Most writing assignments, from elementary to grad school, come with a minimum length requirement. Write about your summer vacation in at least 10 pages. This is done to maintain a minimum level of effort, but it has a bad side effect: It teaches people to fill the page with fluff. We are masters of run-on sentences and unnecessary details because we’ve relied on them since second grade to meet our length quotas.

We’d all be better writers if the standards flipped, and teachers demanded length maximums. Write about all the major Civil War battles in no more than two pages. That’ll force you to make your point and get out of people’s way.

2. Connect one field to others

The key to persuasion is teaching people something new through the lens of something they already understand. This is critical in writing. Readers want to learn something new, and they learn best when they can relate a new subject to something they’re familiar with.

Finance is boring to most, but it’s a close cousin of psychology, sociology, history, and organizational behavior, which many people enjoy. Write about investing in a way that is indistinguishable from a finance textbook and you will capture few people’s attention. Write about it through the lens of a psychology case study or historical narrative, and you’ll broaden your reach. “Pop-psychology” and “pop-history” are derogatory terms. But most “pop” topics are actually just academic topics penned by better writers. Michael Lewis has sold more finance books than George Soros for a reason.

This goes beyond explaining things in ways people enjoy and understand. Connecting lessons from one field to another is also one of the best forms of thinking, because the real world isn’t segregated by academic departments. Most fields share at least some lessons and laws between them. Adaptation is as real in economics as it is biology. Room for error is as important in investing as it is engineering. Explaining one topic through the lens of another not only makes it easier for readers to grasp; it’s a helpful way of understanding things in general.

3. Sleep on everything before hitting the send button

I’m a fan of reading more books and fewer articles.

The reason books can be more insightful than articles isn’t because they’re longer. It’s because they took the author more time to think something through.

An article that takes you a few hours to think of, research, write and publish is subject to whatever mood you’re in during those few hours. Maybe it’s cynical, or pessimistic. Or analytical, or fatalistic. Whatever it is, it might not reflect the calmer, thought-out view of something that took you days, weeks, or months to think about.

I’m shocked at how much I want to change an article after I’ve slept on it for a night, and still want to change it days after it’s published. It makes me realize that if I stewed on the topic for a little longer I’d start thinking about it in different ways. I’d remember better examples, or a better way to phrase a sentence. I’d realize the original argument I made was flawed. Since one sharp example or clever phrase can transform a piece of writing, something you spend twice as long on might not be twice as good as before. It could be ten times better, or more. “The first draft of anything is shit,” said Ernest Hemingway.

A lot of what we write isn’t time-sensitive. You could sleep on it for a day or two or more. And most of the time, you’ll be glad you did.

Also, don’t read the comment section.