Hi friends,

Greetings from Austin!

I'm almost done a fully-refreshed version of my Ultimate Guide to Writing Online. It's a 10,000 word distillation of the best things I've learned about this craft (and what I teach in Write of Passage).

The piece orbits around the three pillars of my writing methodology: (1) Write from Abundance, (2) Write from Conversation, and (3) Write in Public. I continue to believe writing on the Internet is as close to a panacea for all life's challenges as you can find. It's a fast track towards meeting friends, learning faster, and making more money. The guide is a step-by-step process for doing exactly that.

Here's what I want to share this week:

1. ​Hiring at Write of Passage: We're launching a writing course for high schoolers, building a full-on media company, and now that our production studio is done, we're planning to seriously ramp up the quality of writing instruction we share. If transforming education and writing on the Internet fires you up, we might have the job for you. ​
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2. ​Lifting Alone: My short piece about how headphones at the gym are a metaphor for modern individualism.
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3. ​The Paradox of Abundance: Two things are true. First, it’s never been easier to access high-quality information. Second, we’ve never been so inundated with informational junk. If you'd prefer a YouTube video about it, you can watch it here.
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4. ​How Tyler Cowen Writes so Much: I asked one of the most prolific writers I know how he's published a blog post every day for 17 years while simultaneously running one of the world's top university economic departments. Our podcast episode is all about his approach to productivity. (Listen here: iTunes | Spotify)

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Strong Beliefs about Writing

Note: This week is a little different. Instead of sharing a whole article, I'm sharing some favorite excerpts from my Ultimate Guide to Writing Online.

If you'd like me to email you the whole thing when it comes out, click here and I'll send it to you.

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Writing from Conversation

Talking through ideas awakens your primal nature. It’s arson for your scared and timid self — the weakling inside of you that cares too much about what other people think.

On the Internet, the rising costs of Wrong Think stop us from being blunt. Only with trusted friends can most people say the things they actually think instead of the things they’ll be rewarded for saying. For fear of cancellation, they self-censor and hide their coffer of unpopular opinions. Instead of speaking the unvarnished truth, they write to increase their social credit score. First, they lose their edge; then their personality; then the fire that torches their work with the flames of magnetic passion.

So what’s the solution here?

Cry. Scream. Rile yourself up. Rant like a Jewish grandmother. And if you really need to, get whiskey drunk and see what spills out after drink #3. Once the conversation (or the bender) is over, transfer your spiciest takes to the page and write from there.

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Writing is Social

When most people think of writing, they think they need a writing retreat where they can escape society. Like Henry David Thoreau, the author of Walden, being away from society will finally give them the time to avoid the pings and obligations of daily life so they can focus.

Writing from Conversation has the opposite premise: writing is social.

You don’t need to do it alone and being in conversation with others will make you a better writer. Humans are not fully autonomous thinkers; we are social beings. Sometimes, we articulate our best ideas by speaking. Writing from Conversation is one of the oldest ideas out there.

The concept may be new, but the method is not. Writers have been following this “writing from conversation” method for decades. The Bible was spoken long before it was ever written. So were most Greek tragedies. More recently, Ralph Waldo Emerson, one of the top writers of the 19th century, developed his famous essays in public lectures. Those lectures helped him get ideas out of his head, and later, he refined them by writing. When lectures like The American Scholar resonated with the audience, he published them in writing.

Conversations don’t just help us find the truth. They reveal the best way to communicate truth as well. Writing is a one-way medium, which makes it hard to get feedback. But because conversations are bi-directional, we can receive feedback before we ever sit down to write. When we do, we discover places where ideas obvious to us confuse our listeners.

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Developing Your Style

Great artists have a distinct way of doing things.

In the world of art, I think of Van Gogh’s swirling lines; in the world of design, I think of Kelly Wearstler’s flamboyance; in the world of photography, I think of Ansel Adams’ black-and-white landscapes; in the world of acting, I think of Matthew McConaughey’s sayings like “Alright, Alright, Alright.”

Good writers have distinct voices too. From talking to writers, I’ve found that uncommon ones are developed by looking in uncommon places. Some say that Shelby Foote was respected for his Civil War expertise, but beloved for his storytelling. Though he was a historian, he credits Marcel Proust’s novel, In Search of Lost Time as a key inspiration. Even though Proust’s ideas have nothing to do with his area of study (The Civil War), his fingerprints are all over his writing — which is why the details are so vivid. Likewise, the legendary biographer Robert Caro says: “If you want it to endure, the level of the writing has to be the same as great fiction.”

Like Foote, take inspiration from people who are nothing like you. A unique voice can show up in all kinds of ways.

Packy McCormick (a Write of Passage alum) injected humor to the antiseptic world of business writing, and explained ideas with memes. Tim Urban got tired of buttoned-up explanations of intellectual concepts and played around with stick figure drawings instead. Nassim Taleb personifies his ideas by pulling from a cadre of make-believe characters like Fat Tony, an Italian guy with serious street smarts who belongs in a mafia movie like The Godfather.

If you don’t feel like you’ve found your voice, write more.

You ain’t gonna think your way to finding your voice. Don’t get upset with your lack of progress until you’ve published at least 50 articles. As you write, experiment with different styles like a teenager going through phases. One day, they're wearing Hot Topic. Next, they're a jock. And next, they're dressing like their favorite celebrity. Like an angsty teenager, good writers are always experimenting with new styles.

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Photo of the Week: Lessons from Monet

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Though you should follow the conventional writing rules early on, you’ll eventually want to break away from them to develop your style. Painters like Claude Monet offer good model to follow.

Monet's Impressionist style eventually shattered the conventions of art. Before that, his early paintings demonstrated absolute technical mastery. When Monet broke the rules of painting late in his career, he did so intentionally, and that intentionality was enhanced by his mastery of standard techniques.

As the paintings above show, Monet's famous water lilies (which he painted late in his life) had none of the realism he displayed early in his career. Using a more abstract approach, he shattered the rules of landscape art. Unlike other paintings of the time, his water lily paintings have no sky, no horizon, and barely any stable reference points.

The equivalent for writing is that perfect grammar & syntax are a good place to start, but not necessarily the best place to end up. If you doubt this, try reading a piece from somebody who doesn’t understand grammar. It’ll hurt your brain.

Grammar is a necessary, but insufficient condition for good writing. Ideas and personality can transcend perfect grammar, which is why we can read rambling comments for hours on Reddit written by guys in their underwear but get bored with academic writing by the second paragraph.

Don’t get too carried away with style though. It’s like basketball. Master the basics first. NBA players can make behind-the-back passes whenever they want, but my middle school coach was right to immediately pull anybody who tried such a maneuver from the game. Extravagant punctuation can distract from the core message.

When you break the rules, do it deliberately (like Monet).