Hi friends,

Greetings from Austin!

If there's anything I've learned from sleep tracking, it's that consuming alcohol is one of the worst things you can do for your day-to-day health. My sleep is noticeably worse, even with just one drink, which has led me to drastically reduce my alcohol consumption. In retrospect, almost all the worst decisions I've made happened after 4-5 drinks too.

Reflecting on it all, I've discovered that I don't usually drink because I want to get drunk. Rather, I largely drink for the symbolism, regardless of whether its a celebratory pint, a White Claw on a balmy Sunday, or a laid-back glass of wine.

I suspect I'm not the only one, which is why I've invested in companies like Surely that make non-alcoholic wine that actually tastes good. It's the first investment I've made in the food & beverage space because I believe in the mission so passionately. My spidey-sense says that heavy alcohol consumption is going to decline in the next decade and I want to support that trend.

Here's what I want to share this week:
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1. ​How I Write an Essay: Every, a bundle of business-focused newsletters and podcasts, profiled my process for writing long-term essays. We mainly spoke about two of pillars of the Write of Passage system: Writing from Abundance and Writing from Conversation.
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2. ​How to Build a Personal Monopoly: With more than 50,000 views, this workshop with Jack Butcher is the most popular video I've ever published to YouTube. In it, we talk about how creatives should think about differentiating themselves.

Coolest Things I Learned This Week

Write for One Person

I heard that Warren Buffett addresses the early drafts of his shareholder letters to his sister, Dorothy.

Once he finishes it, he replaces her name with "Shareholders."

The lesson: Writing for a huge audience is a fast track to getting writer's block, so write for one person instead.

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Few Cities Whisper Intelligence

Paul Graham has a famous essay where he says that every city whispers something different. San Francisco worships power, New York worships money, and Los Angeles worships fame.

In America these days, whispering intelligence is exceedingly rare. As I walk the streets of just about any major city besides Boston or New York, I'm astonished by how few places celebrate the cultivation of knowledge. Public libraries aren't the cultural centers they once were. Book stores are closing down and the new ones I've seen make it difficult for people to lounge around and read all day. Coffee shops that once had large bookshelves now have uncomfortable seating so people don't sit in the same spot and use the Internet all day. Even the fashionable new clubs like SOHO House are more about looking cool than having intellectual conversations.

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Should You Write With Editing Software?

The quest to improve your writing is like an hourglass. First, you want to learn basic sentence structures and grammatical rules, either by reading a lot or using a tool like Hemingway.

When you're a novice writer, the more the software likes your writing, the clearer it'll tend to read. But too much contemporary writing is so polished that it feels sterile and inhuman. That's why you should eventually work towards a differentiated style where you transcend the suggestions of software and sometimes find ways to make it upset with you.

In that way, feedback is like an hourglass.

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A Photographer's Direction

I recently hired a photographer to take headshots. Though he was kind, I wish he'd been much more authoritarian with me. He's the professional — not me. I hired him to lead the photoshoot, not to ask for my opinions about where to stand for a photo. The shoot took way longer than it should have because he was so timid, and the photo quality was probably worse as a result too.

At the risk of drawing too much from this experience, I often think back to what I wrote in How Philosophers Think:

"When anything you say online can be instantly accessed with a Google search, the costs of independent thinking aren't worth the benefits to most people. Sometimes, I wonder if the fear of offending others contributes to the popularity of abstract art. These days, it seems like every office building, conference center, and apartment complex has the same abstract art on the walls. None of it says anything.

In the words of one person on Twitter: 'Anything with form has meaning, and therefore could invite controversy. The world we are bringing into being will exalt the talentless, the spineless, the shapeless, the meaningless.'"

I won't just point my finger at the photographer. I'll look in the mirror too. I've found myself afraid to be directive or give harsh feedback, even if it's necessary. I'm not saying that we should be mean. Of course we should speak with heart. But the biggest theme of my conversations this week is that so many people are afraid of social backlash that they aren't speaking their mind when it needs to be spoken.

And yeah. Difficult feedback can be hard to give. But because people so rarely receive it, people are often overwhelmed with gratitude when feedback is shared in a kind and generous manner.

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The Trouble with Audiobooks

Modern audiobooks feel so inhuman to me. They have little of the enunciation and emotion that makes the human voice so rich. Besides, because they're made to be listened to at different speeds, they're stripped of their humanity. What we gain in efficiency, we lose in soul.

I love when writers narrate their own audiobooks because even if the recording isn't as "professional," it has so much more soul when you hear from the actual author.
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Photos of the Week

I spent the day planning the next Write of Passage cohort, which begins in late February.

Like every cohort, we put every lecture, assignment, module video, discussion topic, and exercise onto a single board to get a big-picture view of the cohort. Then, we review hundreds of student responses to see what students are happiest about and where we can improve. Every time we run a cohort, we think we're sniffing perfection. And yet, after every cohort, students identify opportunities for improvement.

Here, I'm reminded of Bezos' note about the "divine discontentment" of customers. In his 2018 Letter to Shareholders, he wrote: "Their expectations are never static – they go up. It's human nature. We didn't ascend from our hunter-gatherer days by being satisfied. People have a voracious appetite for a better way, and yesterday's 'wow' quickly becomes today's 'ordinary.'"

That's exactly how we feel.

Online education is changing so fast that the standards of excellence increase every six months. For example, yesterday's incredible video setup is tomorrow's price of admission. But by reading hundreds of qualitative survey responses, we keep our fingers on the pulse of what students value and the roots of their divine discontent.