Write of Passage is a school built for the way the world is today, not the way the world used to be. 

The Internet has made our success possible. Firstly, the Internet is the best matching tool ever invented. It rewards creators. Sharing quality ideas on the Internet is tinder for the flame of serendipity. For those who write well, it’s never been so easy to be discovered. The whole world is connected, and information travels at the speed of light.

The Internet is the best thing to ever happen to education too. By driving the cost of distribution to zero, it altered the economics of education forever. If we were a traditional in-person school and could only serve people in Austin, we’d go out of business. But because we teach online, we can serve the entire world, which also means that we benefit from economies of scale. 

Writing is more important now than ever. All of us have a smartphone in our pocket that can access the accumulated knowledge of humanity from anywhere on the planet and allows us to broadcast ideas in high-definition from almost anywhere. Video might get all the hype, but smart people read, and smart and successful ones read the most. Because of that, we teach writing so people can improve their lives (personally, socially, and professionally). Personally, we help them publish quality ideas. Socially, we help them find their people. Professionally, we 2x their potential by helping them increase their income, the size of their audience or find work that’s twice as meaningful. 

These shifts provide the backdrop for the products we plan to build at Write of Passage. 

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Our Products

We’ll eventually have three products: Flagship, Liftoff, and Business Writing. 

Though we’ve taught more than 1,000 people to date, there’s still so many details to improve, from the way we track their success to the quality of our editing program. We’ll use survey data to nudge students toward mentor groups and resources that match their specific goals. Our students need more support after the five-week cohort ends too. To give it to them, we’ll launch a membership program. We’ll help students solidify friendships, distribute their writing, improve their craft, clarify their Personal Monopoly, and grow their readership in service of real-world outcomes. 

We see writing as a means, not an end. Because of that, we’ll go beyond writing and help students make more money, have more influence, and live a more meaningful life. We’ll launch a recruiting wing to help students find higher-paying jobs, such as becoming a Chief Evangelist for a company that orbits around their Personal Monopoly. 

Flagship will become a hiring pipeline for us too. When we find a student we like, we’ll promote them to an alumni leadership position such as the mentor program, and if they continue to stand out, we may just hire them internally. This will give us a huge recruiting advantage because we can get to know people before hiring them full-time.

We’ll also launch an investment arm, similar to Y-Combinator. When a quality writer with a dynamite Personal Monopoly comes along, we’ll give their company seed funding and pair them with strong operators. Just as Y-Combinator pioneered the Founding Engineer model, we’ll run with the Founding Influencer one. We won’t just produce quality writers. We’ll fund companies too, which will give us a stake in the long-term success of our students. All these goals touch our three core commitments: (1) Publish Quality Ideas, (2) Find Your People, and (3) 2x Your Potential. 

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Liftoff: Our Program for High Schoolers

The big secret in education right now is that the world’s most talented teenagers are much more talented than people realize. Many years ago, I asked one of the world’s most successful angel investors: “How has investing changed?” To which, he replied: “The world’s smartest young people are smarter and more competent than they were 10 years ago.”

He’s right. Teenagers understand cutting-edge digital technology better than even the most talented adults, and the Internet gives them unprecedented access to information that can make them smarter. My experience working with high schoolers confirms his intuition. The challenge is that they attend local schools that squash their ambition and suppress the fire of curiosity inside of them. 

With Liftoff, we’ll train 14-18 year-olds to become online writers. Traditional high schools teach to the lowest common denominator and put a ceiling on gifted students’ potential. There are tens of thousands of high schoolers who are ambitious and obsessed with a topic, but don’t yet know how to channel that passion. As we like to say, “we don’t want kids who like rockets. We want kids who love rockets.” Once they’re writing consistently, we’ll help them build their own websites where they can showcase their best ideas. Instead of writing five-paragraph essays about a novel they don’t care to read, they’ll get to write about their favorite topics with fiery intensity. 

A decade from now, we will have 10,000 kids in the program at once. It’ll be an always-on program. To do that, we need to rethink education and utilize the advantages of big class sizes. Like Peloton, kids will be able to log onto Liftoff 24/7 and join a live writing class or writing group. Time won’t be a constraint. Just log on and write. With that many students, we’ll have an “Internet inside the Internet” where kids can meet people on their intellectual wavelength. Instead of feeling alone, they’ll say: “I can’t believe there are so many other people like me.” 

We’ll hold them to the same expectations as talented adults. Simone Biles’ coach doesn’t want her to be the best gymnast for a high schooler. She wants her to be the best gymnast in the world. We’ll maintain the same lofty standards. We’ll ensure quality by giving professional feedback for every piece and insisting on our stamp of approval before it gets published. 

Kids want to work hard, so long as they can choose their goals and what they write about. Based on that insight, we’re going to do things differently than traditional schools. We’ll only admit committed kids. Once they’re in, we’ll simultaneously hold their hand and push them incredibly hard. We’ll track their participation, publishing frequency, and rate of improvement. If they’re not improving or giving it their all, we’ll kick them out. 

We’ll hire differently than schools. Instead of hiring traditional teachers’ assistants, we’ll hire former Olympians and professional athletes. They’ll work with kids to define their goals, make them more ambitious, and develop a plan to achieve them by writing online. Instead of hiring traditional teachers, we’ll hire YouTubers and TikTokers with a proven passion for education and an ability to connect with teenagers. Instead of letting teacher’s unions run the show, we’ll listen to kids and take their feedback seriously. Add all that up, and Liftoff will become a launching pad for motivated and intellectually curious teenagers with idiosyncratic interests who love to write, but aren’t served by the current education system. 

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Business Writing

Once our program for high schoolers is up-and-running, we’ll move into business writing. Since the pandemic, the world has permanently shifted towards remote work, but many companies are struggling to adapt. 

In an in-person world, work happens synchronously and by talking. In a remote work world, it happens asynchronously and by writing. Decisions need to be documented and writing is the best way to do that. Thinking happens best in Google Docs where people can collaborate asynchronously. You can’t do that with video and audio. It’s no coincidence that two of the world’s most successful Internet-first companies, Stripe and Amazon, are famous for their writing-heavy cultures.

To develop our business writing program, we’ll hire veterans from prominent writing-first companies. In collaboration, we’ll develop methods for project planning, retrospectives, and strategy documents, all with a focus on the changes brought about by remote and asynchronous work. 

Students will learn to surface problems with company leaders through clearly written memos. We’ll show people how writing can increase their impact inside a company. We’ll help companies reduce meetings, improve decision-making, and preserve company knowledge. We’ll become an outsourced training firm for companies who want to build a writing-centric culture in a remote work world. 

Ultimately, we will develop a modern business operating system with writing at the foundation. 

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Building an Independent Media Platform

The marketing of our products will be fueled by the independent media company we’re already building. Right now, the vast majority of people who sign up for Write of Passage find us through my Twitter and newsletter. But moving forward, the Write of Passage brand will shift away from me and towards our community of writers.

We’ve already made a lot of progress in this direction. On the brand side, we now have a brand identity that reflects the Write of Passage spirit. On the content front, we’ve launched our Writing Studio accelerator, published alumni essays on our new website, and launched a dozen editions of the Write of Passage Weekly newsletter. To top it off, we just finished a state-of-the-art production studio in Austin, Texas. Now we’re hiring a video production team to make the best use of it.

We’re building systems to identify, elevate, and distribute great writing from our alumni community. Our team of trained editors will help us scale our alumni collaborations and publish hundreds of essays a year, all under the Write of Passage umbrella. We’ll also bring on several paid Writers in Residence and host themed writing competitions. The bigger our email list becomes, the better our value proposition will be for the writers we want to work with. 

Later this year, we’ll launch a How I Write Podcast. Think of it like How I Built This, but for writing. Additionally, my YouTube channel will be 100% devoted to online writing.

Five years from now, our flywheel will be in full effect. Our independent media platform will let us elevate our students, attract the world’s best writers, and sell our courses. We’ll be positioned as a brand of exceptional quality, worthy of comparison to traditional educational institutions instead of slapdash online courses. We’ll benefit from low customer acquisition costs and extreme brand loyalty. Our company email list will exceed six figures, and analytics will help us direct our subscribers through personalized learning sequences.

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What’s Our Company Like?

Elon Musk was once asked about which product at Tesla he was most excited about. The Model S? Model X? Model 3? None of those. “The factory is the product,” he said. If you can get the factory right, quality cars are inevitable. 

The equivalent for us is our company culture. How do we work? What do we stand for? What do we insist on even when we can’t justify the decision on a spreadsheet? 

Internally, we have a culture of trust, autonomy, measurement, Students First, and Hearts on Fire. One example of trust is our auto-approval process. If you ask for feedback from a superior and don’t receive a response within 24 hours, consider the idea approved. By autonomy, we don’t do micro-management. Leadership will set clear goals and big-picture visions like this one, but everybody can get the job done as they wish, so long as they’re aligned with the direction of the company. By measurement, we don’t just set lofty goals. We measure student outcomes to align on goals, study our shortcomings, and continually improve our product. By Students First, we listen to our students’ challenges, struggles, goals, and dreams. Then we passionately prioritize their needs because we are the most student-centric education company in the world. By Hearts on Fire, we hire people who care deeply and have an earnest commitment to excellence. Everybody who interacts with us should instantly feel our posture of warmth and kindness. Even if it’s just a hunch, they should say: “There’s something different about Write of Passage.” 

In everything we do, we have an exceptionally high quality bar. I once attended a conference hosted by Patrick Collison, the CEO of Stripe, which is one of the best-run companies in the world today. Upon arrival, every attendee received a brochure with directions. At the bottom, it said: “Please contact somebody on our staff if something isn’t impeccably perfect.” 

By the standards of the world, that’s insane. Unreasonable, even. But standards like that are what it takes to do great work. The world’s quality bar is way too low. 

Write of Passage is a high-end, quality brand. We are the Four Seasons of writing instruction. We aren’t just in the business of education. We’re also in the business of hospitality. We stand for excellence. We judge ourselves by our own standards, not the outside world’s. In service of our students, we must continually resist the quiet creep of mediocrity. 

Everything we do will orbit around our core commitments to students:

1. Publish Quality Ideas
2. Find Your People
3. 2x Your Potential

The time has come to build a transformative writing school built for the way the world is today, not the way the world used to be. Write of Passage is that school and we are the ones to build it. Between Flagship, Liftoff, and Flight, we have an opportunity to change how writing is taught, friendships are made, ideas are shared, and careers are built. This is our own Write of Passage.

Beware of stories with strong Narrative-Market Fit. 

My inspiration for this idea comes from Silicon Valley, where investors look for Product-Market Fit. Founders tinker with product ideas until they eventually catch fire and start growing fast. And when the puzzle pieces finally click, founders say they’ve found Product-Market Fit. 

Media narratives are governed by an analogous idea: Narrative-Market Fit. 

It happens when a story reflects the zeitgeist, and specifically, what media consumers are thirsty to hear. 

Just as companies with Product-Market Fit are more likely to be funded, stories that reflect the zeitgeist and serve readers what they want to hear are more likely to be published. When a narrative is hot, writers are incentivized to focus on them at the expense of important but less popular stories — and sometimes, the truth. Instead of fitting the narrative to reality, they fit reality to the narrative.

The media runs on narratives because hot narratives usually sell better than truth. 

So whenever you read something, ask yourself: “Does this story have Narrative-Market Fit?” 

The more it has, the less you should probably trust it.

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Cover Photo by AbsolutVision on Unsplash

Start your business once you find five people who would purchase your product. 

A lukewarm “maybe” doesn’t count. You need an emphatic “YES.” Look for five people, then start building. Crucially, the percentage of people who say yes doesn’t matter much, but you get extra points for getting five “yes” answers for a niche software-based product that doesn’t exist yet.

I call this signal to build the “Five Finger Trigger.”

It works because niches on the Internet are bigger than you think, even after you account for the fact that niches on the Internet are bigger than you think. If you can find people in real-life who want your product, thousands of people online will likely want it too, provided that it serves a global audience. 

Don’t judge the merit of your idea based only on what you see in your day-to-day life. It’s too limited to reflect the scale of the market you can reach online,¹ never mind the opportunities that exist solely in the digital world. Moreover, people are more likely to express their weird interests online than offline, so you can build a successful online business with interest from a smaller percentage of people than you think. That’s because a small percentage of the very large number of people who use the Internet is a big customer base. 

Note that the Five Finger Trigger applies best to software businesses. 

That’s because it assumes a low cost of building a prototype for your product. For example, if you know how to code, you can build your first software product by yourself for less than $100. Software is inexpensive, so the most expensive variable is your time. You can find your first customers for cheap by writing online or running a small batch of advertisements on Google or Facebook. 

In contrast, this model doesn’t work for starting a solar panel company because it costs millions of dollars to build a prototype, and “five friends said they’re down” isn’t the kind of certainty that venture capitalists are looking for. 

Once you have five interested people, build the product for yourself. Don’t do market research. It’s vastly over-rated at the early stages of product development, especially when your costs are low, your risks are small, and the market of potential customers is so big. Besides, selling your first product will teach you more about your customers than years of market research. Move fast and build what you wish already existed instead. If you do, your intuition will be smarter than the suggestions of your customers. 

When you launch, share your product with your group of five. If you can delight them despite the inevitable flaws in the early versions of your product, keep building. If they don’t like it, try another prototype. Ask what they don’t like, and narrow into the pain point you want to solve. At this stage, if you use the product — because it helps you, not because you’re its creator — keep going. If you don’t use it because it genuinely helps you, take a step back. No matter what you do, keep your costs low and your team small in the early days. 

As an example of large-scale successes you may not hear about in “real life,” my friend Nathan Barry started an email marketing service for online creators called ConvertKit. Instead of following other people’s suggestions, he designed the platform for his personal writing process. Even though probably no one at your Thanksgiving table has heard of it, the company now earns more than $20 million in annual recurring revenue. 

I used the Five Finger Trigger to start my business too. 

I never thought I’d become a writing teacher and only started Write of Passage after five friends asked me for online writing advice in the same month. The idea for the course was theirs, not mine — I wouldn’t have made the course without that critical mass of requests for advice. With their encouragement, I skipped the market research phase and built the course I wish existed when I started writing online. But others expressed concern. One mentor who runs a major investment fund doubted Write of Passage’s validity, even after it became a profitable business. He told me there wasn’t a market for online writing education. In retrospect, he underestimated the scale of the Internet and the number of people who wanted to write online because he runs and invests in businesses tied to the physical world. 

People like my mentor underestimate the number of Internet businesses in the economy, in part because these numbers aren’t reported in the media. According to one recent article by Will Schreiber, “Of the 3,000+ software companies acquired over the last three years, only 7% got TechCrunch, Recode, HN, or other mainstream tech coverage.” 

Creating online gives you personalization and scale. The Internet feels both bigger and smaller than the physical world. It feels bigger because it exposes you to an order of magnitude more people, opinions, and events. But it feels smaller because it’s so easy to find exactly what you’re looking for.

To be sure, the Five Finger Trigger is easier to pull when you have an online audience. Both Andrew and I benefited from a loyal group of readers who doubled as the target market for the products we sold. Those small audiences helped us grow our businesses without paid marketing in the early days, the bulk of our audience growth came after we launched our products. 

So if you want to start an online business, don’t worry if you don’t see your idea validated on a massive scale. Look for five people who would purchase your product. Once you find them, pull the Five Finger Trigger and commit to creating.

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Each week, I write two popular emails. Monday Musings is a collection of the coolest things I learn every week. Meanwhile, Friday Finds is a links-only newsletter where I only share the kinds of ideas you won’t find anywhere else. 

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¹ The Internet is the best matching tool ever invented. Uber matches drivers with riders, Craigslist matches buyers and sellers, and Tinder matches young singles.

Here are the 50 ideas that changed my life.

These are my guiding principles and the light of my intellectual life. All of them will help you think better, and I hope they inspire curiosity. 

1. Inversion: Avoiding stupidity is easier than trying to be brilliant. Instead of asking, “How can I help my company?” you should ask, “What’s hurting my company the most and how can I avoid it?” Identify obvious failure points, and steer clear of them.

2. Doublespeak: People often say the opposite of what they mean, especially in political language. It allows people to lie while looking like they’re telling the truth. As George Orwell famously wrote in 1984, “War is peace. Freedom is slavery. Ignorance is strength.” 

3. Theory of Constraints: A system is only as strong as its weakest point. Focus on the bottleneck. Counterintuitively, if you break down the entire system and optimize each component individually, you’ll lower the effectiveness of the system. Optimize the entire system instead.

4. Preference Falsification: People lie about their true opinions and conform to socially acceptable preferences instead. In private they’ll say one thing. In public, they’ll say another. 

5. Faustian Bargain: A man once sold his soul to a demon in exchange for knowledge. At first, it seemed like a smart trade. But the man lost in the long-run. Tragically, what the man lost was more valuable than what he earned. In short, he won the battle but lost the war. 

6. Mimetic Theory of Desire: Humans are like sheep. We don’t know what we want, so we imitate each other. Instead of creating our own desires, we desire the same things as other people. The entire advertising industry is built on this idea. 

7. Mimetic Theory of Conflict: People who are similar are more likely to fight than people who are different. That’s why Civil Wars and family feuds create the worst conflicts. The closer two people are and the more equality between them, the greater the potential for conflict.

8. Talent vs. Genius: Society is good at training talent but terrible at cultivating genius. Talented people are good at hitting targets others can’t hit, but geniuses find targets others can’t see. They are opposite modes of excellence. Talent is predictable, genius is unpredictable. 

9. Competition is for Losers: Avoid competition. Stop copying what everybody else is doing. If you work at a for-profit company, work on problems that would not otherwise be solved. If you’re at a non-profit, fix unpopular problems. Life is easier when you don’t compete. (Hint: don’t start another bottled water company). 

10. Secrets are Hidden in Plain Sight:  Most people think of secrets as Easter eggs. They assume that if a secret is important, it’s necessarily going to be hard to find. The best ideas can come from things that are so well-known that they aren’t well-seen. 

11. The Never-Ending Now: The structure of our social media feeds blinds us to history, as it causes us to live in an endless cycle of ephemeral content consumption. The structure of the Internet pulls people away from age-old wisdom. 

12. Demand Curves Slope Down: The harder something is to do, the fewer people will do it. For example, raise the price of a product and fewer people will buy it. Lower the price and more people will buy it. Economics 101.

13. Look for Things That Don’t Make Sense: The world always makes sense. But it can be confusing. When it is, your model of the world is wrong. So, things that don’t make sense are a learning opportunity. Big opportunities won’t make sense until it’s too late to profit from them. 

14. The Wisdom of Paradox: Logic is the key to scientific truths, but paradoxes are the key to psychological ones. When it comes to the human condition, the deepest truths are often counter-intuitive. When you find two opposites that are both true, start exploring.

15. Law of Shitty Click-Through Rates: Most marketing strategies have a short window of success, as click-through rates decrease as tactics mature. For example, the first banner-ad has a click-through rate of more than 70%. Now we avoid them with ad-blockers.

16. Russell Conjugation: Journalists often change the meaning of a sentence by replacing one word with a synonym that implies a different meaning. For example, the same person can support an estate tax but oppose a death tax — even though they are the same thing.

17. Opportunity Cost: By reading this tweet, you are choosing not to read something else. Everything we do is like this. Doing one thing requires giving up another. Whenever you explicitly choose to do one thing, you implicitly choose not to do another thing. 

18. Overton Window: You can control thought without limiting speech. You can do it by defining the limits of acceptable thought while allowing for lively debate within these barriers. For example, Fox News and MSNBC set limits on what political thoughts they consider acceptable, but in the grand scheme of things, they’re both fairly conventional. The political spectrum stretches far beyond the ideas they entertain, but ideas outside their limits are shunned. 

19. Planck’s Principle: Science doesn’t progress because people change their views. Rather, each new generation of scientists has different views. As old generations pass away, new ideas are accepted and the scientific consensus changes.

20. Bike-Shed Effect: A group of people working on a project will fight over the most trivial ideas. They’ll ignore what’s complicated. They’ll focus too much on easy-to-understand ideas at the expense of important, but hard to talk about ideas. For example, instead of approving plans for a complicated spaceship, the team would argue over the color of the astronaut’s uniforms.

21. Table Selection: This idea comes from poker, where you’re advised to choose your opponents carefully. That means you shouldn’t compete against the best people. You don’t need to get good at doing difficult things if you get good at avoiding difficult things. If you want to win, pick an easy table and nail your execution.

22. Goodhart’s Law: When a measure becomes a target, it ceases to be a good measure. One hospital took too long to admit patients so a penalty was given for 4+ hour wait times. In response, ambulance drivers were asked to slow down so they could shorten wait times. 

23. Gall’s Law: A complex system that works is invariably found to have evolved from a simple system that worked. A complex system designed from scratch never works and cannot be patched up to make it work. You have to start over with a working simple system.

24. Hock Principle: Simple, clear purpose and principles give rise to complex and intelligent behavior. Complex rules and regulations give rise to simple and stupid behavior.

25. Parkinson’s Law: Work expands to fill the time available. People don’t want to look like they’re lazy, so they find extra tasks to tackle, even if they’re trivial. If you have six months to complete a project, it will take six months to complete. Set deadlines accordingly.  

26. The Second Law of Thermodynamics: The world tends towards disorder. That’s why your room becomes messier and messier over time. It’s also why an engine converts only ~35% of its energy into useful work. Time moves towards increasing one direction: increasing entropy. 

27. The Paradox of Specificity: Focus isn’t as constraining as it seems. In the age of the Internet, when everybody has Google search and personalized social media feeds, differentiation is free marketing. The more specific your goal, the more opportunities you’ll create for yourself. Narrowing your aperture can expand your horizons.

28. Emergence: When things interact, they often birth new, unpredictable forms. Therefore, the sum total of a system is more than its component parts. As a system evolves, its structure can transform — just like how water becomes cold water until it turns into ice. 

29. Occam’s Razor: If there are multiple explanations for why something happened and they are equally persuasive, assume the simplest one is true. In the search for truth, remove unnecessary assumptions. Trust the lowest-complexity answer. 

30. Hickam’s Dictum: The opposite of Occam’s Razor. In a complex system, problems usually have more than one cause. For example, in medicine, people can have many diseases at the same time.

31. Hormesis: A low dose of something can have the opposite effect of a high dose. A little bit of stress wakes you up, but a lot of stress is bad for you. Lifting weights for 30 minutes per day is good for you, but lifting weights for 6 hours per day will destroy your muscles. Stress yourself, but not too much.

32. Robustness Principle: Be conservative in what you do, be liberal in what you accept from others. It’s a design guideline for software and a good rule for life: Hold yourself to a higher standard than you hold others to.

33. Legibility: We are blind to what we cannot measure. Not everything that counts can be measured, and not everything that can be measured counts. But people manage what they can measure, so society repeats the same mistakes.

34. Horseshoe Theory: Extreme opposites tend to look the same. For example, a far-right movement and a far-left movement can be equally violent or desire a similar outcome. People on both sides are more similar to each other than they are to people in the center. 

35. Availability Cascade: A self-reinforcing cycle that creates collective beliefs. An idea will gain traction once it enters the mainstream, which triggers a chain reaction, which causes lots of people to adopt it not because it’s true but because it’s popular. 

36. Creativity Begins at the Edge: Change starts away from the spotlight. Then, it moves towards the center. That’s why the most interesting ideas at a conference never come from the main stage. They come from the hallways and the bar after sunset

37. The Copernican Principle: The more we learn about astronomy, the less it seems that earth is special. It’s a small part of the universe, and each human is a small part of the earth. We are all spinning through the solar system — nowhere near the beginning or end of time.

38. Personal Monopoly: Corporations reward conformity, but the Internet rewards people who are unique. If you work in a creative field, strive to be the only person who does what you do. Find your own style, then run with it. Create intellectual real estate for yourself.

The Internet rewards unique people.

Find your unique combination of skills, interests, and personality traits.

I call this a Personal Monopoly.

Become the only person in the world who does what you do.

Then, tell the world by sharing your knowledge. pic.twitter.com/FcvdiEjo5Q

— ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ (@david_perell) May 10, 2020

39. The Paradox of Consensus: Under ancient Jewish law, if a suspect was found guilty by every judge, they were deemed innocent. Too much agreement implied a systemic error in the judicial process. Unanimous agreement sometimes leads to bad decisions. 

40. Penny Problem Gap: Economists assume demand is linear, but people’s behavior totally changes once an action costs money. If the inventors of the Internet had known about it, spam wouldn’t be such a problem. If sending an email cost you $0.001, there’d be way less spam. 

41. The Invisible Hand: Markets aggregate knowledge. Rising prices signal falling supply or increased demand, which incentivizes an increase in production. The opposite is true for falling prices. Prices are a signal wrapped in an incentive.

42. Base Rate: The average outcome for an event over time. They’re like batting averages for life, and they work best with big sample sizes. For example, if you’re starting a business, avoid the restaurant business where margins are low and competition is high.

43. Circle of Competence: Define the limits of your knowledge. Hint: the limits are smaller than you think. That’s because being an expert in one area doesn’t make you an expert in anything else. Be clear about what you know and don’t know. 

44. Convexity: If you want to be lucky, look for opportunities with big upsides and low downsides. In addition to increased optionality, your errors will benefit you more than they harm you. Convex payoffs let you tinker your way to success and innovation. 

45. The Go-For-It Window: Large gaps between accelerating technologies and stagnating social norms create lucrative new business opportunities. But they are only available for a short time when people can capitalize on the difference between the real and perceived state of the world. For example, 2007 was the perfect time to launch the iPhone, but Google Glasses launched too early.

46. Via Negativa: When we have a problem, our natural instinct is to add a new habit or purchase a fix. But sometimes, you can improve your life by taking things away. For example, the foods you avoid are more important than the foods you eat.

47. The Medium Is the Message: We pay too much attention to what is being said. But the medium of communication is more impactful. For example, the Internet’s impact on humanity has a bigger influence than anything that’s said on the Internet. 

48. Resource Curse: Countries with an abundance of natural resources such as diamonds and fossil fuels tend to have less economic growth and worse development than countries with fewer natural resources. 

49. The Paradox of Abundance: The average quality of information is getting worse and worse. But the best stuff is getting better and better. Markets of abundance are simultaneously bad for the median consumer but good for conscious consumers.

50. The Map Is Not the Territory: Reality will never match the elegance of theory. All models have inconsistencies, but some are still useful. Some maps are useful because they’re inaccurate. If you want to find an edge, look for what the map leaves out.  

51. Baker’s Dozen: The key to good hospitality is to delight your guests with an unexpected gift. If you run a hotel, leave a chocolate on the bed. If you run a bakery, give your customers one extra bagel. If you write an article like this, share an extra idea. 

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Each week, I write two popular emails. Monday Musings is a collection of the coolest things I learn every week. Meanwhile, Friday Finds is a links-only newsletter where I only share the kinds of ideas you won’t find anywhere else.

No teacher had a bigger impact on me than Miles Chen. 

He was my high school advisor, teacher, and golf coach. He was famous for his love of pork buns. Everybody talked about the restaurants he took us to and the Chinese food he brought to school. But people outside our golf team never experienced Miles’ wisdom, his appreciation for Asian culture, or how the games we played on the golf course laddered up to a galaxy of life lessons. 

Miles did his own thing. He cared little for norms. Unlike other teachers, he recognized that the bond you build with your students is more important than any material knowledge you impart to them. In class, he created his own curriculum, so his teaching was less predictable than a Cardi B interview. He rarely gave tests and reluctantly handed out grades at the end of the semester. Even though he was a triple major from UC Berkeley — painting, physics, and astrophysics — he wasn’t trapped down by rigid educational norms. He taught with the magic wand of humor, as opposed to the bureaucratic seriousness of his colleagues.

To date, Miles was the only teacher who made math feel like more than symbols on a page. Through his teaching, the universe came to life as his equations twinkled like stars in the nighttime sky. 

Now that I’m a teacher, I want to be more like Miles. Actually, I want our entire school system to create teachers like him. 

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When Rigidity Goes Wrong

The federal government has tried to improve education by imposing rigid top-down standards. The education system has stagnated because of increased standardization. Standardized grades. Standardized tests. Standardized curriculums. 

And yet, educational outcomes have not improved despite the increased standardization. As Tyler Cowen showed in The Great Stagnation, there has been no significant improvement in the average reading score for 17-year-olds since 1971 or the average mathematics score since 1973¹. Despite flat test scores, America doubled its per-person education spend during that time frame. Americans are losing ground, even on standardized measures. Two out of three children don’t meet reading proficiency standards according to a test administered by the National Center for Education Statistics. Worse, 20% of American 15-year-olds still don’t have the expected reading skills of a ten-year-old. Teachers are teaching to the tests, but students still can’t pass them. 

Worse, the emotional side effects of modern education are worse than the disease itself. Kids aren’t meant to be locked in a classroom for 7 hours a day, 5 days a week, for 12 years of their lives. That’s not education. That’s criminal. I’m reminded of a story about Sarah, the 12-year-old daughter of a family friend. Sarah’s always struggled with self-esteem. To cope, she attends weekly therapy, takes an antidepressant called Prozac, and when the weight of emotional toil is too heavy to bear, she cuts herself. But Sarah’s mother says she’s been happier since the Coronavirus quarantine began. Without school, she’s rediscovered her love for learning. As her mother said: “Traditional learning environments can be very stressful for anxious kids. I just feel blessed within the chaos, an emotional break is good for my girls.” 

Sarah isn’t sick. The system is. 

We design our schools to drive children mad. But instead of questioning the system, we medicate children and double-down on the system that makes them miserable in the first place. In that way, we’re like pill-obsessed doctors who ignore the field of preventative health and prescribe medications faster than activists hand out flyers. 

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Why Brasilia Failed

When considering the problems with education, I’m reminded of the failure of Brasilia, the capital city of Brazil. As James Scott described in his book, Seeing Like a State, the utopian project began in 1957. 

The genesis of this top-down view begins with modernism, the idea that rational design would make rational societies. Modernism grew out of the order of World War II military units. Straight lines. Sharp, right angles. No room for randomness. 

Designers believed the modernist style would eradicate the miseries of the human condition, from hunger and disease to tyranny and inequality. In architecture, there was no room for the personal touch of a craftsman — the inverse of the Middle Ages when builders had independence and didn’t have to follow top-down master plans. But the lowly individual would not be trusted under the cold rule of modernism. Only the elites had the technical and scientific training to rationalize society, leaving no room for local knowledge or individual creativity.

Inside Brazil, the modernist-inspired city of Brasilia was known as “The City of Tomorrow.” It was backed by mountains of cash and fountains of national pride. Juscelino Kubitschek, the president of Brazil when plans for the city were conceived, said the city would give Brazilians “fifty years of progress in five.” The city might have shined in photographs, but the infinity highways and sterile apartment blocks were socially lifeless. The perfect city never arrived because Brasilia was built for tower-looking architects instead of the street-walking citizens who actually lived there.

What should we learn from Brasilia?  

We should not assume everything important can be measured and only what we can measure is real. The view from a map cannot capture the culture of a city. Much of what makes a culture thrive looks messy and purposeless on a map. Humans need chaos. Not everything important can be understood, so decision-making should happen at the local level. 

Look at a map of Amsterdam and Brasilia, and you’ll see stark differences. Amsterdam was born in the 12th century when fishermen living along the River Amstel built locks to protect themselves from floods. The name Amsterdam comes from the former name of the settlement: “Aemstelredamme,” which means “dam in the river Amstel.” Since those first settlers arrived 800 years ago, the city has evolved gradually. The city never had a central planner so the lines on a modern map of Amsterdam are hard to follow. So are the streets, where cars, cyclists, trolleys, and pedestrians compete for space. Today, tourists get lost in the labyrinth of narrow roads. 

Brasilia is the opposite. On paper, the lines are straight and elegant. Boxy buildings intersect with boxy parks and boxy roads. Architects who use rigidity and uniformity to organize a system like a city or a school to appeal to order often destroy what appeals to the heart. That’s why, despite its theoretical perfection, Brasilia lacks life while Amsterdam buzzes with energy. 

In my own Write of Passage course, each student is matched with a mentor and a small group of students. Like neighborhoods in a city, each small group develops its own culture during each cohort. Some students start Slack groups. Others write together in weekly Zoom calls. All of them develop a shared language of inside jokes. Students who live in the same city take the course offline to meet for drinks in-person and edit each other’s essays. 

As a teacher, I want my course to feel less like the empty plazas of Brasília and more like the vibrant streets of Amsterdam. 

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The Issue With Federal Standards

Miles’ class never had a textbook. He clashed with other faculty because he never followed a traditional or standardized teaching style. Other teachers rolled their eyes, but Miles didn’t care. As a co-founder of my high school, he couldn’t be fired. Perhaps because he was safe in this way, he was able to reject the one-size-fits-all style of lectures and tests. 

Unlike other teachers, Miles taught with a playful style. Most teachers taught in droning lectures and measured what we learned by our ability to memorize what they said. Borrrrringgg. But Miles’ classes were fun, so I tried harder in them. Of all the astrophysics projects he assigned, my favorite was a to-scale map of the universe running from our classroom in San Francisco across the entire United States. According to my model, the outer stars stretched beyond New York City — 14.5 billion light-years away. Until then, I had never grasped the immense, ever-expanding scale of the universe. 

He didn’t teach astrophysics to prepare students for college. Instead, he worked to make us appreciate the vastness of space and the wonders of the nighttime sky. He made the subject material come alive. He never assigned more than three questions of homework every night, so I had time to engage with each question. Out of all my science classes in high school and college, Miles’ class was the only one I got an A in. 

Standardized testing is to school as Brasilia is to architecture. A top-down architecture with noble intentions but lifeless results. These top-down standards stop students and teachers from taking risks. A friend and former educator says AP teachers in some school districts receive a $50 bonus for every student who receives a score of at least a “3” on their subject’s AP exam. Students at the Success Academy charter school systems in New York score high on standardized tests at the cost of creativity and independent thinking. Their students are trained to be bureaucrats from a young age. The dogma: Follow the rules. Listen to your elders. Don’t take too many risks. 

One former teacher told me she was shocked at the level of anxiety students had when she asked them to choose their own essay topics because students follow directions so they can improve test scores. 

Far-away bureaucrats are too involved in the lives of our children. Even if their intentions are strong, the results have been disastrous. Curriculum decisions should be pushed down the ladder as far as possible. Otherwise, we’ll end up with the same one-dimensional system that’s led to rising costs and stagnant test scores. 

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Grades: False Indicators of Learning

Grades destroy curiosity. Too many kids learn for the sole purpose of raising their GPA because that’s what the system incentivizes². From an early age, I observed that my success in school depended more on my grades and less on how much I learned. In college, even though I wrote essays on my own and worked as an intern in New York City for companies like Skift, I was almost kicked out of my fraternity because my GPA was below 3.0. Likewise, my college counselors evaluated me on two metrics: grades and SAT scores. Neil deGrasse Tyson once said: “When students cheat on exams, it’s because our school system values grades more than students value learning.”

Our standardized curriculum forces us to think too narrowly. I see this first-hand running a Write of Passage summer camp for 9-12-year-old kids. Students come from countries like Brazil, Panama, Argentina, Canada, India, and Pakistan. Instead of telling kids what to do, we encourage them to identify a problem and explore their own interests. During a recent cohort, they made comic books, top motion videos, games out of recycled materials, YouTube videos to raise awareness about animal cruelty, cooking tool prototypes, a scratch animation on recycling, a newsletter to save dogs in Panama, and a recipe for healthy smoothies that actually taste good. 

Trusting kids to express their individuality yielded the same unexpected charming diversity that makes a city like Amsterdam so special. Reflecting on her learning experience, one student said, “The stuff we learn in school has little to do with our real life. It doesn’t really matter. What matters is we pass the test so we can go on to the next grade.” 

In traditional school, by narrowing our focus to an incomplete but easy-to-measure optimization figure, grades distract us from learning itself. Kids are discouraged from diving down rabbit holes because they aren’t on the syllabus. But as any passionate learner will tell you, your curiosity will help you learn more than any syllabus ever will.

For an example of an independent learner, consider Nassim Taleb, the author of five best-selling books including The Black Swan. At the age of 13, he set a goal to read for 30-60 hours per week. “Only the autodidacts are free,” he says. Choosing to learn on his own prevented him from becoming a “swallower” (somebody who “swallows” school material and whose knowledge is limited to what’s on a curriculum). Instead of fighting his ADHD, he ran with its tide. His natural craving for stimulation drove his scholarship. When he got bored with one book, he moved on to the next one. That way, he could get bored with a specific book, not the act of reading itself. 

In contrast, school taught me to hate reading. Studying Shakespeare hurt my brain, and I had no interest in Paradise Lost. But during my junior year of college, after I experienced the joy of Twitter, I stopped taking school seriously and started learning on my own instead. If a book was boring, I stopped reading it. If an assignment didn’t interest me, I did the bare minimum. Good grades became an afterthought, but my pace of learning exploded. And yet, I couldn’t prove my accelerated learning speed. My slight GPA improvement hardly reflected my newfound love for ideas.

My passion for learning wasn’t the problem. Tests were. When I needed to ace an exam, I prepared not by engaging with the material but by downloading a QuizLet set and memorizing flashcards in the library. The process was so mind-numbing that Adderall pills were worth their weight in beer during finals week.

More frustrating than my own scores was watching kids who spent most of their time partying receive better grades on tests. Those students were sometimes the “best” students and were often the ones who least wanted to engage in intellectual conversations. Ideas served a utilitarian purpose: getting good grades. Getting a 3.5 GPA was the benchmark, and if you hit it, you could drink guilt-free on the weekends and tell friends you were crushing it like a red Dixie cup. 

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Grades and the Goodhart’s Law Trap

Goodhart’s Law states, “When a measure becomes a target, it ceases to be a good measure.” Two famous examples come to mind. In one rat-infested city, the local government offered a bounty for rat tails. But instead of killing rats, enterprising individuals followed the incentives of the system. They captured rats, cut off the tails, released the tailless rats to breed, and turned in the tails for cash. Over time, the number of rats increased³. 

More famously, Soviet factories were rewarded based on the number of nails they produced. Factory managers responded by producing tons of tiny, useless nails. Before adding an explicit production inventive, factories saw a strong correlation between the productivity of a plant and the number of nails it produced. But once the target for more nails became explicit, the correlation between the productivity of a plant and the number of nails produced disappeared⁴. 

As with all clever concepts, the Germans have a fancy word for the phenomenon: Verschlimmbessern — to make something worse while trying to make it better. 

In a system where students don’t pursue grades as an end state, grades are a strong proxy for learning. But just like the rat-infested city and the Society nail factories, students who focus solely on grades won’t necessarily learn the way we want them to. They’ll follow the curriculum instead of their curiosity and build easy-to-quantify skills instead of interesting ones. Students who struggle in school (trust me, I was one of them) will stop trying or label themselves as stupid while smart students study no more than they need to get ace the class. Likewise, teachers stop productive classroom discussions so they can follow the lesson plan. But as any creative person knows, the best ideas come from the kinds of tangents we disincentivize. 

We should avoid designing our school system with the same blind spots that destroyed Brasilia. Our grades-driven, curriculum-dependent school culture assumes that only what we can measure is real and that everything real can be measured. All this direction destroys the chaos that is vital to learning. 

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Where Messy Systems Thrive

As we’ve seen, the top-down obsession with cleanliness has predictable failure modes. Even if it’s hard for humans to see, messy designs are often more intelligent than orderly ones. 

For example, computer-generated AlphaZero chess algorithms can control the board in ways humans can’t measure. It’s as if they have X-Ray vision while the rest of us see visible light. When I was taught chess as a kid, I used a points system where each piece was worth a given number of points. Queens were worth nine, castles were six, knights three, and pawns one. Computer programs, on the other hand, make more complicated assessments. In addition to capturing an opponent’s piece, they can manipulate it so it becomes less useful over time. The strategy of disabling an opponent’s piece without taking it is hard to measure, but it’s remarkably effective. 

Likewise, a software program called Evolving Floor Plans tried to optimize a building’s floor plan to minimize construction materials, shorten fire escape paths, and provide access to views. The result had none of the straightness and edginess of Brasilia. There were no long hallways. Instead, the more efficient computer-generated designs looked random and chaotic. 

To return to our theme of cities, Jane Jacobs, who is arguably the most famous urbanist in American history, called New York City’s West Village her favorite neighborhood. Based on its steep real-estate prices ($3,500/month for a small studio apartment), city residents agree. Jacobs fought for diversity, density, and dynamism. Her favorite neighborhoods had mixed-use zoning with a cocktail of homes, restaurants, shops, culture, and entertainment. West Village’s maze of streets wasn’t pre-planned like Brasilia. Rather, the fusion of home and business emerged organically, leading to beg-your-friends-to-eat-there restaurants like Bleecker Street Pizza and the Big Gay Ice Cream Shop. 

As I think back to high school, Miles was my most influential teacher because he operated in a West Village style. 

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Like the chaotic streets of West Village, the best educational experiences are at odds with bureaucratic modes of design. We’ve created a group of high-achievers who don’t have tools to navigate real-world problems. A former teacher once told me her AP students had the highest social anxiety, the least confidence, and were the most naive — even though they were the most advanced. Howard Gardner makes a similar point in The Unschooled Mind: “Students who receive honors grades in college-level physics courses are frequently unable to solve basic problems and questions encountered in a form slightly different from that on which they have been formally instructed and tested.” 

Focusing on theory at the expense of action is like learning to drive in an online course. Words like velocitation, which describes the feeling of going too fast on the highway without realizing it won’t help you navigate the roads. But no matter how fast you pass the driver’s education exam, you won’t learn to drive until you put your hands on the wheel, hit the gas pedal, and navigate the chaos of a busy intersection. 

Most learning is hard to define. 

The difference between curriculum-based learning and real-world learning is like the difference between the gym-strength and real-world-strength. The same people who only workout in gyms would lose a neighborhood street fight. As Nassim Taleb writes in Antifragile: Things That Gain From Disorder: 

“[Gym-obsessed bodybuilders’] strength is extremely domain-specific and their domain doesn’t exist outside of ludic — extremely organized — constructs. In fact their strength, as with over-specialized athletes, is the result of a deformity… I thought it was the same with people who were selected for trying to get high grades in a small number of subjects rather than follow their curiosity: try taking them slightly away from what they studied and watch their decomposition, loss of confidence, and denial.” 

Rigid curriculums turn students into over-specialized weightlifters. Ask them about business and they’ll tell you the basics of accounting, but they’ve never fought to meet payroll in the thick of an economic crisis. Ask them about literature and they’ll quote Shakespeare’s sonnets, but they can’t tell you what it’s like to edit a sentence for the 30th time and still hate it. Ask them about nature and they’ll tell you the history of Yosemite National Park, but they’ve never seen God paint an orange sunset on Half Dome’s granite face. Ask them about baseball and they’ll tell you Barry Bonds holds the homerun record, but they’ve never experienced the shit-in-your-pants terror of trying to hit a 95-mile-per-hour fastball⁵. They don’t know about real knowledge because that only occurs when you escape the order of the classroom. 

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Teaching Like a State

With our current methods of measurement, we will hurt the quality of education if we try to control every aspect of it. Top-down teaching has limited effectiveness. Teachers who know their students are able to anticipate the needs of a classroom better than any faraway Washington suit-and-tie ever will. We should begin by relaxing federally-imposed academic standards. The more we allow top-down planning to influence our schools, the more they’ll resemble Brasilia. Our schools will lack culture and the allure of grades will give students rat-tail syndrome. 

More importantly, teaching like a state is the fastest way to get rid of teachers like Miles. 

After Miles left my high school, the golf team found a new golf coach named Tony. On the first day of practice, Tony mentioned he would not be like Miles. He didn’t mention the invisible things. The long one-on-one car rides, Miles’ peculiar sense of humor, or his glittering passion for physics. Instead, Tony mentioned the most visible element of Miles’ influence: the food. No more Pocky. No more potstickers. 

Teachers thought we liked Miles because he brought us food when it was a small — but visible — perk. We loved Miles because of the larger, but hard to define personality traits that made him so unique. From the perspective of the school, everything is the same. The season still begins in March, kids practice five days per week, and they still play at the Presidio golf course. But to the kids, the golf team hasn’t been the same since he left. The laughs aren’t as loud, the bonds aren’t as strong, and pork buns are nowhere to be found. 

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Each week, I write two popular emails. Monday Musings is a collection of the coolest things I learn every week. Meanwhile, Friday Finds is a links-only newsletter where I only share the kinds of ideas you won’t find anywhere else. 

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Footnotes

¹ This is originally from a 2009 report from the National Assessment of Educational Progress.

² This was an insightful comment from Ana Lorena Fabrega, who I run Write of Passage Summer Camp with: “A lot of what passes for “learning” in schools is really an imitation of learning. Think about it, even students who have done well in class completely forget the course material after completion of the course. Given the system we’ve created, what incentives do kids have to value “learning” over grades? It doesn’t value curiosity or exploration. Kids learn to play the game and figure out what to do in order to pass. This disconnect between a desire to learn and what happens in schools carries over and continues into college.”

³ This story may be apocryphal. I’ve heard many people tell it, but I wasn’t able to find the original source.

⁴ Even the biggest companies are guilty of Goodhart’s Law. For example, IBM is one of the least innovative technology companies even though it receives more patents than any other Silicon Valley company each year. Patents were originally correlated with innovation. But now, the correlation between patents and innovation has fallen.

 ⁵ Yes, this paragraph is inspired by Robin Williams in “Good Will Hunting.”

Thank you to Ana Lorena Fabrega, Kathleen Martin, and Zander Nethercutt for their help with this essay.

The Internet is inspiring a people-driven model of online learning.

It’s the end of intellectual silos and soul-crushing specialization. 

The traditional learning environment inhibits the cross-pollination of ideas. It’s led to a world of isolated subjects where cutting-edge discoveries in fields like physics and mathematics can only be understood by a small number of people. 

To see why, consider the layout of our university campuses. Earlier this year, I audited a philosophy class at Columbia. Before class, I finished my reading in the coffee shop at the journalism school on the western side of campus, met my friend at the business school on the northern side of campus, and walked with him to the philosophy building on the eastern side of campus.

To show the fragmentation of academia, the graph of the sciences below highlights the disconnect between fields as measured by co-citations between fields. 

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How Learning on the Internet Contrasts This Model

We’re desperate for an alternative to siloed learning. With its people-driven approach to information discovery, online learning will inspire a generation of polymathic thinkers. A kingdom of epiphanies is waiting for intellectual ambassadors who can connect the dots across disciplines. 

The People-Driven Method is driven by influencers instead of professors and the serendipity of the Internet instead of the rigidity of a classroom curriculum. It’s also a more natural way to learn because humans are wired to be interested in other people. For proof, look at People Magazine. Beginning in the 1970s, it had the largest paid audience of any American magazine. Today, it’s the most valuable magazine in the world. 

How can you benefit from people-driven learning?

The best way to get started is to form a Personal Monopoly.

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How to Benefit From People-Driven Learning: Build a Personal Monopoly

You can benefit as a creator and a consumer. 

As a creator, you should build content based on a personal monopoly — your unique combination of skills, interests, and personality traits. 

The Internet creates winner-take-all markets, which reward people who define and master their own areas of expertise. Unlike school, it rewards people who create instead of compete. In school, we are taught the same things. We learn the same subjects so we can ace the same standardized tests, attend the same colleges, and work for the same prestigious companies.

But the Internet rewards people who are different. It rewards learners who escape the well-worn path and fuse their interests to create their own discipline instead. 

Here are three examples: 

• Meagan Morrison: She built a career around travel, writing, and a drawing style defined by bright colors, fashionable outfits, and sweeping brush strokes.

• Peter Attia: By focusing on healthspan (how many years you’re healthy for) instead of only lifespan (how long you live), he created his own way of thinking about longevity.

• Casey Neistat: Neisat fused his passion for filmmaking, skateboarding, and consumer technology, to pioneer vlog-style YouTube videos. 

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How You Can Take Advantage of People-Driven Learning

Building a Personal Monopoly is the best way to thrive as a creator, but there are two ways for consumers to take advantage of people-driven learning. 

1. Follow the Trader Joe’s Strategy

2. Become a Fan

I’ll take each in turn.

1. The Trader Joe’s Strategy: This strategy revolves around finding an online curator to be your learning guide. They will do the hard work of finding information for you, so you can spend less time searching for ideas and more time consuming them.

   What makes a good online curator? 

   A good curator will reduce the number of options you have to consider. In that way, they’re like Trader Joe’s. The typical grocery store has 35,000 items in a store, but the typical Trader Joe’s only has 3,000. The chain scouts and sources their products, so customers don’t have to sort through tons of choices. Compared with other grocery stores, Trader Joe’s has fewer options with higher average quality. It’s no coincidence that of all the grocery stores I know, Trader Joe’s has the most loyal customers.

   Example: Take a look at James Clear’s list of great speeches and Patrick O’Shaughnessy’s list of great books.

2. Become a Fan: Resist the conventional wisdom to start by reading all a creator’s books. If you’re anything like me, you do this naturally. I’m spending more time reading summaries and less time reading books. Yes, I feel guilty about it. But no, it’s not a bad thing. Start with articles, summaries, and podcast interviews, and only buy their books when you’re ready to devote 15-20 hours to exploring their ideas. 

   Example: I want to learn about Gilles Deleuze, who is one of the most important philosophers of the 20th century. His ideas are famously complicated, so I familiarized myself with his ideas by listening to summaries. I started with a 15-part series from John David Ebert and a series of lectures by Justin Murphy. Then, I listened to podcasts hosted by Deleuze scholars. Unlike books, lectures are affordable and I can listen to them while I’m on-the-go, which makes the learning process efficient and enjoyable. 

Similarly, studying Marshall McLuhan led me to Lewis Mumford’s critiques of technology, Water Ong’s perspectives on literacy, and Martin Gurri’s analysis of the political impact of information abundance. All those ideas led to the most popular essay I’ve ever written: What the Hell is Going On. True to the people-driven learning mentality, studying McLuhan helped me find my personal monopoly: teaching online writing. Following the intellectual breadcrumbs of his mind is the best caution engine I’ve found, better than any curriculum or social media feed. 

People-driven learning is more fun and efficient than the traditional learning model. As you curate your social media feeds, you can access an entire library of ideas instead of having to slog between university buildings to engage with new ideas. As you cross-pollinate ideas, you’ll find the synthesis of new ideas and make unprecedented connections between them.

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Each week, I write two popular emails. Monday Musings is a collection of the coolest things I learn every week. Meanwhile, Friday Finds is a links-only newsletter where I only share the kinds of ideas you won’t find anywhere else. 

Join 25,000+ subscribers and enter your email below.

We live in a society of adult-like children and childish adults.

Kids have never had more information at their fingertips, so they’re growing up faster than ever. From a young age, they can watch violent war clips on YouTube, Dan Bilzerian videos on Instagram, and Shakira getting low at the Super Bowl halftime show.

Yet, even though they grow up fast at first, they mature into adulthood slowly. Young people today are often unable to become financially independent or walk the path of a meaningful life. As a result, we’re left with a culture of childish adults who are allergic to commitment and unable to see the light in adulthood.

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Adult-Like Children 

Video destroyed the innocence of childhood. Before the invention of television in 1950, knowledge about full adult life was guarded from children in books. Kids were shielded from money, death, violence, and especially, sex. Kids couldn’t read until their teenage years, so adults concealed taboo topics in writing.

That changed with the invention of television, which took ideas out of books and put them on video. Text ceased to be a barrier so children were exposed to mature content from a young age. For example, kids can’t understand Fifty Shades of Grey, but because of Instagram, they know how to twerk like Miley Cyrus. As Ben Sasse wrote in The Vanishing American Adult: 

“Practically nothing [on television] is taboo or off limits. Because television doesn’t know or care who’s watching, the medium effectively “adultifies” children while infantilizing adults; it doesn’t judge its viewers, nothing is shameful.”

When I was a kid, ESPN ran on channel 38. Four clicks away, on channel 42, I routinely stumbled upon soft-core pornographic images like Brittany Spears’ Toxic music video. 

In our video-first age, children and adults watch the same things on television, which was never true for books. 12-year-olds don’t read Hegel. By moving from a book-centric culture to an image-centric one, we created a Peter Pan Generation of childish adults who refuse to grow up.

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Childish Adults

While children act like adults, adults also act like children. With the rise of video, the social—and moral—transition from childhood into adulthood disappeared. Maturing into literacy lost its significance because kids already knew the secrets once reserved for adulthood. As Neil Postman wrote: “Everywhere one looks, the behavior, language, attitudes, and desires—even the physical appearance—of adults and children are becoming increasingly indistinguishable.” 

I agree with Postman: the barriers between childhood and adulthood have disappeared. Responsible only for ourselves, we’ve extended the age of adolescence and postponed the transition into adulthood. Young adults who begin by postponing marriage and parenthood are increasingly dependent on their parents for housing and financial support. As the $16 billion plastic surgery market shows, we prefer the purity of youth to the scars of wisdom. 

Gone are the coming-of-age rituals which once carried the maturing mind forward. In Beliefs and Rites, anthropologist Lorna Marshall writes about little Nyae Nyae !Kung boys who used to practice shooting and play with bows and arrows. The transition into adulthood came when they began to hunt with their fathers. But the “Rite of First Kill” was the most important ritual, which arrived after a boy had killed his first big meat animal. To mark the portal into adulthood, boys were seared with life-long scars to show they had been “cut with meat.” 

Today, we have no such black-and-white rituals. Drinking alcohol? That starts in high school. Legalized voting? Nobody celebrates that. Getting your driver’s license? Not as cool as it used to be. Bar Mitzvah? People remember the party, not the service. 

For the first time in more than 130 years, Americans 18 to 34 are more likely to live under their parents’ roof than with a spouse or partner in their own home. Today, 25% of Americans between 25 and 29 live with their parents, compared with 18% just over a decade ago.

The aversion to adulthood is most evident in cities, where people lack family, religion, and community. Since the Enlightenment, people in The West have chosen the path of more freedom at every turn. But we made a Faustian bargain. In search of individuality, we freed ourselves from family, church, and community. 

In 1800, three-quarters of American workers were farmers. They lived in big, sprawling households. Until 1850, roughly three-quarters of Americans older than 65 lived with their kids and grandkids. Industrialization and cheap transportation changed that. People left their home towns and flocked to big cities. The landscape of marriage changed in response. In 1932, one-third of married couples lived within a five-block radius of each other before they tied the knot. The average woman was married at 20, men at 23.

Our jobs have changed, too. Graduates from top universities overwhelmingly work for professional services companies in management consulting and investment banking. Sure, they have sexy brands to make mamma and papa proud. Some even get to ride the private jet. But the vast majority of people I know at these companies are plotting to escape like they’re stuck on Alcatraz. 

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The Hopelessness of Adulthood and the “Adulting” Meme

The childish adult phenomenon is well captured by the “adulting” meme. On the surface, the meme is a response to the overwhelming number of things you need to do as an adult: go to the gym, get your work done, answer emails, make the bed, clean the kitchen, sweep the floors, file taxes, buy groceries, put the kids to bed. 

On a deeper level, though, I think this meme stems from a perception of adulthood as a hopeless enterprise. It represents a mentality that encourages people to retreat into a nihilistic, bubble-wrapped cocoon of deferred responsibility.

That passivity is the mark of a generation overwhelmed by contemporary life. They lack clear role models for how to behave. Our anything-goes world suffers from a tempest of uncertainty about how to “adult.” Noble virtues—honor, courage, loyalty—are dismissed.

I lived this first-hand in college, where my friends and I tipped our bottles to the “best four years of our lives.” Tuesdays were for beer trivia, Thursdays were for bar crawls, Fridays were for house parties, and Saturdays were for day drinking.

Can you blame us? In the age of iron-grip parenting, college felt like the only time in our lives when we wouldn’t have to act like professionals. In my own social circle, the pursuit of an Ivy League diploma began before we were aware of it. The siren at the start of the race sounded on the first day of elementary school, when our mothers packed our lunch boxes just as we tightened our Toy Story backpacks and marched into the classroom. Instead of playing in the backyard, we built our resumes with extracurriculars. Piano lessons, SAT prep, theatre, volunteering, study abroad — our childhoods were curated for the college admissions knife fight. 

Those college years were sold as the peak. We never thought life could improve after graduation, and we dreaded the monotonous, desk-chained rituals of adulthood. All that rebellious energy was set to fire by movies like Animal House and Project X, which celebrated the freedom of life without adults. College was the only time we’d have autonomy, so instead of discovering our telos, we flew the flag of anarchy. 

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Trying to Adult

I’m writing this essay not because I’m above these problems, but because I suffer from them too. I am surprisingly childish. At 25, I still can’t handle the demands of adult life, from filing my taxes to incorporating an LLC, without my parents’ help. When tax season rolls around, I still call my father. Booking the best flights? Same thing. Sometimes, I feel like my life is on the brink of collapse— stitched together with second-hand duct tape. 

I’m learning. I first confronted my aversion to responsibility in 2018, when I had just been laid off from a job and was struggling to build my first business. Desperate for clients, I called my mentor Brent. When he asked why I wanted to work for myself, I said, “I want the freedom to do what I want.” 

With grace and generosity, Brent encouraged me to reconsider my lust for freedom and embrace virtues like duty, thrift, and commitment. He explained to me that responsibility can be more rewarding than freedom alone.

Brent’s critique of freedom went against everything society told me to do. The ultimate millennial dream is “Stay single, pursue a four-hour workweek, and become a digital nomad. Most of all, stay free.”  

This lifestyle is superficially glamorous, but ultimately unfulfilling. It’s a life without the love that only devotion can provide. Eventually, it resembles the sampling tables at Costco: sure, you can try a cosmopolitan buffet of snacks, but cheese from a disposable paper cup will never give you the nutrients you need.

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We Need to Replace “Freedom From” with “Freedom To”

Ben Sasse, the aforementioned Senator of Nebraska and the former President of Midland College distinguishes between “freedom to” virtues and “freedom from” ones. Every year at Midland, the faculty surveyed its students. Time and again, students described canceled classes as the best part of their four-year college experience. 

Sasse writes: 

“Adolescents put off adult responsibilities for as long as they can, sometimes by choice but more often as a result of circumstances and trends beyond their comprehension. In the face of unprecedented prosperity and freedom from convention, the generation coming of age is stuck in a hazy, extended adolescence, never allowed simply to be children, and yet also rarely nudged to be fully adult.”

Outwardly, we said “college was the best four years of our lives.” But inwardly, we had no hope for the future. There was no cultural message that life could improve after graduation. Conversations about our dreams were as rare as waking up on Saturday morning without a hangover. Without faith in a better tomorrow, we embraced degeneracy and avoided our to-do lists. Our “adulting” culture prizes ephemeral happiness over eternal fulfillment — it’s a culture where kids age fast and adults mature slowly.   

I hope that in the future, we’ll see meaning and responsibility as two sides of the same coin. With adulthood comes the freedom to pursue a vocation, the wealth to nurture your community, and the wisdom to raise the next generation.

A life well-lived demands a forward-leaning embrace of responsibility. We should drop the freedom from mindset and welcome the freedom to learn, the freedom to work, and the freedom to tackle meaningful challenges. Otherwise, coming-of-age Americans will float without direction, drifting like a log in the ocean. 

In the end, until we can restore the innocence of childhood, appreciate the wisdom only literacy can provide, and find beauty in the wrinkles of old age, we will feed a culture of adultish children and childish adults.  

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Thanks to Ellen Fishbein for helping me write this essay.

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Great performers have a wall of heroes. Figures who set their standard of excellence. 

They provide energy in moments of sloth, direction in moments of confusion, and most of all, inspiration in moments of apathy. 

All kinds of high performers are moved by the achievements of their heroes. Tiger Woods measured his childhood progress against the (then) best golfer of all time: Jack Nicklaus. Golf Digest published a list of Nicklaus’ career accomplishments after the 1986 Masters, along with his age at every significant achievement. He won his first U.S. Amateur at 19 years old and his next when he was 21. At 22, he earned his first professional victory. By 26, Nicklaus had won two straight Masters Tournaments. And later that year, as young Woods sat in front of his living room television, Nicklaus became the youngest player to win all four majors. 

Tiger printed out the list of Nicklaus’ wins and taped it to his bedroom wall. For the entirety of his childhood, Nicklaus was the first person to greet him in the mornings and the last person to say goodbye at night. 

Creatives should have heroes too. Writers, designers, painters, musicians, and dancers. All of them. 

My wall of writing heroes is lined by three figures, all of whom whisper in my ear as I write this sentence. It includes Marshall McLuhan, Robert Caro, and Gregory David Roberts, each for different reasons. 

Marshall McLuhan reminds me to explore. To synthesize never-before-been-synthesized ideas to create new, panoramic explanations of the world that get richer with time like the lyrics to a favorite song. Robert Caro reminds me to explore my subjects from every possible angle, as if I’m adding an extra dimension like a Cubist painting. And finally, Gregory David Roberts reminds me to turn the world into a frozen tableau of wonder. 

To be sure, those aren’t the only writers I revere. I envy Jia Tolentino’s knack for capturing the strangeness of contemporary life, John O’Donahue’s ability to describe the indescribable, and Tim Urban’s ability to make me laugh louder than a flushing airplane toilet. 

My heroes write with me, no matter where I am. 

In a world where complacency passes for excellence, these writers set my standard. They exist outside of time, so they’re unfazed by the turbulence of daily life. I surge with envy when I read their work. They are my judges and my coaches, my friends, and my teachers. Without them, I’d cave to the temptations of mediocrity. 

Who are your heroes? 

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Thanks to Andy Matuschak for the conversation that inspired this essay.

If you want to write essays like this, subscribe to my free 9-day writing course. In it, you’ll learn about note-taking, The Netflix Principle, and why you should write in small chunks.

“I hate tennis.” 

This is the opening message of Andre Agassi’s biography, Open. Agassi was the son of a tyrannical father who cared for little beyond creating a tennis champion out of his little boy. Steered by his father’s heavy hand, and often against his will, Agassi rose to be the number one player in the world. To others, the top was an unachievable dream. To Agassi, it was a toxic ball of fire.

The fame, the ridicule, and the decades of living a life he despised caught up to Agassi. His anger became resentment, his resentment became rage, and his rage descended into a decision to dump crystal meth on a coffee table, cut it, and snort the powder up his nostrils with the speed of a U.S. Open serve. 

Why did Agassi break under the pressure of discipline? How does his story represent so many of us?

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Why We Drug Children 

I hated school. The cycle of waking up early, going to school, being disciplined, feeling inadequate for not being smart, and dashing to mandatory soccer practice after school made my blood boil. Sports, music, theater, public speaking, community service. The obligatory activities never ended. The routine made me apathetic. There were so many things on my schedule as a kid that I stopped attending Bar Mitzvahs and birthday parties. 

Inside the classroom, my personality wasn’t suited for the traditional education system. My math was terrible, I couldn’t follow directions, and I had the reading comprehension capacity of a squirrel. I spent most of my time behind a shield of self-protective numbness only to erupt with volcanic rage once I got home.  

For years, I didn’t have the words to describe my frustration. My family shouldered the weight of my anger. Trapped in a system of heavy-handed control, I yelled at my parents in cries of violent desperation. 

In retrospect, I acted out because I couldn’t be a kid. In middle school, I was sent to the principal’s office so many times that I tallied my visits on the arm rest of the chair outside his office. Still today, we dehumanize children by locking them in classes they despise with teachers who have to act as babysitters by giving them time-outs until they shut up and follow the rules. 

If we did the same thing to adults between the ages of 45-60, we’d have a revolt. But when we do this to kids, we justify it as “preparing them for the real world.” First, we ignore their cries for agency. Then, we squash their curiosity with rigid curriculums like AERO and the Common Core that move too slow for the bored and too fast for the curious. Worse, the tyrannical curriculum structure teaches children to accept the world as it exists. Students can’t modify the syllabus. They have to accept it as it’s given to them. By doing so, we kill the joy of learning, strip agency away from our children, and in turn, rob them of their humanity. 

We’ve stopped treating children like people. 

The rigidity of childhood is a new phenomenon. It began in the 1990s, when the number of hours devoted to childcare began to rise after three decades of decline. The increase in parenting time was the largest among college-educated mothers who increased their childcare time by more than nine hours per week. Much of the culprit goes back to parents who spend two decades biting their nails about their children’s college prospects. Ivy League or failure. 

Why are parents so anxious? 

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Why Parents Are Anxious About College Acceptances

Boomers grew up in a credentialed world where people were defined by the school on their college diploma. Students benefited from college not because of the education they received, but because of sexy diplomas and tight personal networks. 

Personal networks matter too. One Union College study found that fraternity students saw a 0.25 drop in GPA, but a 36 percent rise in lifetime income known as the “Bro Wage Premium.” 

Meanwhile, the average college diploma isn’t the signal of prestige it once was. The number of Americans with a college degree has risen by more than 300% since 1970, leading to credential inflation where people need more and more education just to stay in place. 

The knife fight for college admission has spawned a bitter legacy debate. Now that so many people work for big companies, parents can’t always give their kids the family business. Instead, the best that parents who want to leave an easter egg for their children can do is use their legacy status to help children get into their alma mater. Some donate buildings, and others bribe the admissions officers. 

More and more parents are encouraging more and more children to fight zero-sum battles like the college admissions process. This childhood rat race is packaged as ambitious, even though it actually rests behind a facade of sheep-like, anxiety-creating complacency. 

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How Kids Respond to Anxiety

In an article in The Atlantic, George Packer quotes an anxious seventh-grader who said, “If you fail a math test you fail seventh grade, if you fail seventh grade you fail middle school, if you fail middle school you fail high school, if you fail high school you fail college, if you fail college you fail life.”

Parents stress over college acceptance, which creates stress for teachers who teach to the test, which creates stress for kids who can’t experience the creativity of traditional childhood. According to one Pew Research study, 70% of teens list “anxiety and depression” as a major problem in their local community. Another study found that half of PhD students experience psychological distress. All these emotional struggles lead to an overmedicated society. 

To their credit, my parents didn’t drug me. I had all the features of a kid who would have binged ADHD medications like shots at a New Year’s party. No matter how badly I acted, my parents never caved into the twisted logic that leads doctors to hand out prescription pills faster than candy on Halloween. For years, I looked as unhealthy as I felt. Face-peeling acne. Uncontrollable anger. No self-esteem. By middle school, my behavior was so bad that we stopped going on family trips. To silence the stress of it all, I found ways to escape reality (thank the lord for Madden and RollerCoaster Tycoon) without popping a single pill. 

School taught me the wrong lessons.

As Ivan Illich wrote in Deschooling Society: “The pupil is thereby ‘schooled’ to confuse teaching with learning, grade advancement with education, a diploma with competence, and fluency with the ability to say something new.” My grade school teachers said the tough standards would prepare me for high school, my high school teachers said the tough standards would prepare me for college, and my college teachers said the tough standards would prepare me for the professional world. But it was a lie. As I sat in class, I felt like a domesticated animal, training to serve the needs of institutions instead of myself. 

Kids who don’t conform to the narrow demands of the education system are diagnosed with ADHD and prescribed addictive psychoactive drugs. As Peter Gray, the author of Free to Learn, has observed, these drugs are designed to suppress a child’s instincts so they can sit down, shut up, and slave through busywork:

“Nobody knows the long-term effects of these drugs on the human brain, but research with animals suggests that one effect may be to interfere with the normal development of the brain connections that lead children generally to become more controlled, less impulsive, with age and maturity. Perhaps that helps to explain why today we see more and more cases of ADHD extending into adulthood. As with lots of psychoactive drugs, the drugs used to treat ADHD may be creating long-term dependency.”

Tragically, the growth in ADHD prescriptions has accelerated since the turn of the century. In an article called “The Drugging of the American Boy,” Ryan D’Agostino argues that many of these diagnoses are false. Today, 6.4 million children between the ages of 4-17 have been diagnosed with ADHD. Almost 20 percent of all American boys will now be diagnosed with ADHD by high school, a 37 percent increase since 2003. Instead of building a system that respects the biology of kids, we are destroying childhood — one synthetic pill at a time.  

Just as high schoolers numb their passions so they can beat their classmates on the SAT, adults trade joy for money by answering emails until their head hits the pillow. 

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Why Adults Live for the Weekend and Binge Alcohol

New York, where I live, is defined by its live-for-the-weekend culture. Young professionals who move to New York have dreams of building fame, wealth, or power by climbing the corporate ladder. The most talented university graduates disproportionately fall into sectors like law, investment banking, and management consulting. To numb the pain of sitting at a desk for 50-80 hours per week and the Hunger Games levels of competition for a small number of competitive positions, New York’s social scene revolves around a culture of binge drinking. 

Recently, I had dinner with a friend in Manhattan who is frustrated with his management consulting job and looking for a way out. We’ll call him Justin. Since the moment I met him, he’s justified his heavy alcohol consumption with unwavering persistence towards societally valued goals — good grades and a job to make his parents proud. Justin graduated top of his class in high school, magna cum laude in college, and now works for one of the big four accounting firms. In service of his job, he travels more than Carmen San Diego. In each destination, he executes the same security audit for the same kinds of companies in the same kinds of industries. Three years out of college, Justin sees no path towards autonomy or away from hyper-specialization. 

Over chicken dumplings and ramen noodles, my friend said, “My parents tried so hard to make me successful but never stopped to ask if I was enjoying myself. They are proud of what I’m doing, and since I work for an impressive company, they just assume I’m happy.”

I can relate, even though I’ve only had one job (which lasted seven months). I distinctly remember the dusky December days I worked there, when the dark night came early and the winter winds blew cold. Every morning, before I stepped into the office at 9 am, I said goodbye to the blue sky of liberty. I’d push a button to the fifth floor, stammer towards my desk, and stare into my computer until half my co-workers had left and there were three stars in the sky. From Monday through Friday, I saw less than 30 minutes of sun per day. 

To combat my sedentary routines, I lived for the weekend. Drinks on Friday? I’d be there. How about Saturday? You bet. 

The madness of weekends made up for the lethargy of the weekdays. Instead of tying myself to a chair, I paraded around Manhattan with a choir of friends and a drink in my hand. Eventually, I learned about New York’s culture of after-work happy hours where yes-men take their edge off with Heinekens and vodka sodas.

In retrospect, I’m not proud of these habits. But I can’t blame myself. New York’s substance-ridden culture is a natural reaction to the stress and trappings of life in a 43rd-floor cubicle. 

Success shouldn’t be synonymous with how good you are at forcing yourself to do what you don’t want to do. We should rebel against a world that rewards mechanical levels of specialization. In the will to succeed, we subject ourselves to toxic and health-destroying work environments. Instead of questioning our habits, we counterbalance the pain of work with a ritual of reckless bar crawls. Instead of conforming the system to human nature, we conform human nature to the system. 

Too many of my close friends are on antidepressants. They also suppress the body to the mind. Most of them don’t have time to exercise, the freedom to soak up the sun, or control over how they spend their time. In the face of rising drug use, we give people antidepressants instead of re-thinking the system that leads to depression in the first place. Without the drugs, they won’t be able to tolerate their intolerable work environments. 

That’s not to mention self-medication. American alcoholism is a worsening problem. Since the 1990s, the percentage of Americans who drank at all increased by nearly half, while high-risk and disorderly drinking rose by 20 percent and 12 percent respectively. Meanwhile, according to the Gallup Poll below, the number of Americans who report that drinking has been a cause of trouble in their family has tripled since 1974. Here we see a pattern among children and adults. The same routines that create high-achieving students and later, successful professionals, can cause people to respond in dangerous and unintended ways. 

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“The Suite Life of Zack & Cody”: It Turns Out Having Nothing But Fun Isn’t So Much Fun

Conventional wisdom says both kids and adults will waste their time if you give them total freedom. I take the opposite perspective. We underestimate the number of people who will indulge in hedonism for a short while before realizing its emptiness and embracing a life of purpose and direction. 

I’m reminded of an episode of “The Suite Life of Zack & Cody,” a Disney Channel show about two hyperactive teenage boys who live in a hotel. In one of my favorite episodes, they are tired of adults who tell them what to do: “Eat your veggies,” “Do your homework,” “Don’t play hockey in the lobby.” The boys travel to an alternate reality where there are no rules, so they can do whatever they want. At first, they celebrate with reckless play. They binge on room service and gallons of Jelly Beans. Then they play basketball in the hotel ballroom. But after a few days, the endless play loses its luster. Zack and Cody miss their mother’s “do your homework” discipline and the “stop running in the lobby” strictness of the hotel manager. Bored by endless freedom, they escape the alternate reality in favor of a normal life, and a forward-learning embrace of personal responsibility.

When we discipline people against their will, we create negative repercussions. In that way, stringent rules are like the First Law of Thermodynamics. Also known as the Law of Conservation of Energy, it says that energy cannot be created or destroyed. It can only be transferred from one form to another. The First Law of Thermodynamics comes to life whenever you boil water. As you crank up the fire on the stove, heat is transferred from the stove to the kettle. You can’t cheat the laws of physics, no matter what you do. As the water boils, the kettle begins to whistle and condensation begins to build like a San Francisco fog. Likewise, suffocating a person’s free will for too long will result in harmful second-order effects for individuals and society at-large. This is the price of discipline. 

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My Motivation

My process of becoming an adult is a story of overcoming my childhood rage. I’ve learned to channel my hyperactive tendencies into healthy habits like a daily gym routine and writing on this website.

Furthermore, my vendetta against the education system has driven me to build two schools: one for adults and another for young kids. Both are responses to the tyranny of childhood education. Unlike the all-too-familiar compliance mindset of traditional schools, my schools have no grades, diplomas, or mandatory assignments. We encourage students to trust their instincts and tackle projects of their own choosing. As we do, we operate with a hand heavy enough to orient them but light enough for them to march with agency. 

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The Choice of Focus

Sports hold a mirror to the human condition. The beauty, the struggle, and the pain of it all. Through competition, we learn morality, patience, persistence, sacrifice, and discipline. But by hitting a small yellow ball, Agassi suffered from the cacophony of resentment that accompanies a life of hostile discipline. 

Agassi writes: 

“It’s no accident, I think, that tennis uses the language of life. Advantage, service, fault, break, love, the basic elements of tennis are those of everyday existence, because every match is a life in miniature. Even the structure of tennis, the way the pieces fit inside one another like Russian nesting dolls, mimics the structure of our days. Points become games become sets become tournaments, and it’s all so tightly connected that any point can become the turning point. It reminds me of the way seconds become minutes become hours, and any hour can be our finest. Or darkest. It’s our choice.”

Stuck in the depths of despair, Agassi made a choice to play instead of quit. For the first time, Agassi marched to the beat of his own drum instead of his father’s. Once he chose tennis, his mindset shifted. He said: 

“Even if it’s not your ideal life, you can always choose it. No matter what your life is, choosing it changes everything.”

Moved by his decision, Agassi escaped the valley of addiction. He climbed the rankings to become the number one player in the world for a second time. This time, he did it with panache and a light spirit. 

Reckless freedom is an empty enterprise. People want to be productive members of society. In the end, the eternal meaning of self-directed purpose triumphs over the hollow ephemerality of pleasure. But like Andre Agassi, people need to realize this truth through the hard knocks of personal experience. 

Don’t get me wrong. I’m not advocating for a world of careless anarchy where people are slaves to their instincts. We need teachers to keep children safe and parents to keep them healthy. But children don’t need the minute-by-minute schedules of a Fortune 500 CEO. 

If we want to raise healthy, high-agency children, we should give them the freedom to make decisions without removing them from the consequences of those decisions. Giving children agency now will help them avoid a dark cycle of work, pain, and reckless release in the future. Even if a life of indulgent hedonism is fun in the short-term, it ultimately leaves a void in the heart. 

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Thanks for Ana Fabrega for co-writing this essay with me.

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We live in the age of Performative Reading.

Consuming as many books as possible has become a competitive sport for knowledge workers who want to show off their intellectual curiosity. To do so, they race through books like they’re collecting mushrooms in Super Mario Kart. 

This modern reading habit stems from a deep-rooted cultural insecurity. We no longer believe that one idea can be transformative. 

Instead, we follow a binge-watching, TED-Talks-before-bed strategy where we hop from epiphany to epiphany without investigating any of the ideas. Our obsession with learning has descended into an obsession with consumption, as if the answers we need to take action are lurking in the next book, the next documentary, or the next Netflix show. But consuming more information does not necessarily make you more competent. 

In contrast to the sprint to read every book on Kindle, Charlie Munger once said: “Take a simple idea and take it seriously.” Many of the most successful people I’ve studied have found their edge by putting their faith in one big idea. They’ve committed to the idea, and studied it so much that its implications have become second nature. 

Two people, Rich Barton and Richard Mosse, stand out. 

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Rich Barton’s Big Idea: Power to the People

Rich Barton has built his career by “bringing power to the people.” Consumer technology markets are notoriously difficult. Repeatable success is almost impossible, so the founders of most successful consumer companies almost never start a second major company. But Barton has founded three billion-dollar companies: Expedia, Zillow, and Glassdoor. 

On the surface, these three companies look different. But under the hood, they are mirror images of each other. All of them attacked a big opaque market, such as travel, real estate, and corporate recruiting. They used the Internet to remove the information asymmetry between establishment gatekeepers and ordinary consumers. As Kevin Kwok wrote in Making Uncommon Knowledge Common: 

“Barton career can be summed up by his mantra “Power to the People”. His companies take power from the incumbents and give it to consumers. 

Instead of trying to hoard information, they are on the side of consumers and giving them more data transparency. Glassdoor revealed how employees really felt about companies. Zillow shed light on what any house was worth. Expedia let people see the prices and availability of flights and hotels without talking to an agent.

Expedia wants to be the first place you go when you travel. Glassdoor wants to be the destination when you’re thinking about companies to work for. And Zillow wants to be the place you go to look at real estate.”

To attack the travel market, Expedia publicized the prices for flights and hotels that were once only available to travel agents; to attack the real estate market, Zillow used the Zestimate to give people a ballpark number for what their house was really worth; and to attack the corporate recruiting market, Glassdoor gave people honest reviews about the experience of working at a company that were more honest than what recruiters or companies provided. 

Data network effects kicked in once these companies gathered a critical mass of information. With it, they used Google search and word-of-mouth as their top acquisition channels, both of which are low-cost. All three companies became encyclopedias of critical information on flights, hotels, houses, and corporations. Crucially, all of them capitalized on the parallel wave of smartphones and consumer familiarity with digital platforms. These companies could not have been built before the Internet. By riding the Internet wave, Barton built three companies that look different but all employ the same One Big Idea.

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Richard Mosse’s Big Idea: Photograph the Invisible

In January 2018, I visited the National Gallery of Art in Melbourne, Australia. There, I was mesmerized by Richard Mosse’s Incoming exhibit, where he captured the experience of refugees from North Africa and the Middle East using military-grade thermal detection cameras. Usually, the technology is used for military surveillance, often to identify and track targets. Instead of capturing visible light, it detects body heat, which the human eye cannot see. 

Mosse represented his subjects in unfamiliar ways by turning them into inverted silhouettes without identity. Each person glows with body heat. Instead of being divided by race, viewers are united by the shared temperature of humanity. 

All of Mosse’s work follows the one big idea of using cameras to highlight aspects of the world that are beyond the grasp of the naked eye. His central idea is simple: use photographs to illuminate the invisible.

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The Reality You Cannot See

The world is more complex than we see. When you look at the world through the lens of your One Big Idea, you see opportunities others are blind to. In that way, the One Big Idea is just like the Electromagnetic Light Spectrum. There are light waves flying all around us — radio, microwave, infrared, visible, ultraviolet, X-Ray, and Gamma Ray. But humans can only see visible light, even though we know the other ones exist. Consistent with the themes in the aforementioned Richard Mosse paintings, the light waves we see determine our view onto the world.

I held a mirror into my own reality blindness during a recent trip to my friend Nick’s apartment. When I walked into his living room, he winked, smiled, and said he had something to show me. I knew I was in for a treat. Nick grew up in a small town in Pennsylvania. His father was an engineer who taught him how to work with his hands and be handy around the house, a skill I don’t have. Together, we climbed a shaky ladder to an attic he’d converted to a small bedroom, where the bed suspended in mid-air using four ropes that connected to 100-year-old Carnegie Steel beams. From the mattress, I looked through the glass windows above and saw the Freedom Tower, an army of airplanes, and a chorus of stars twinkling over the New York sky. 

Nick had converted dead space in his apartment into one of the coolest rooms I’d seen in New York. I would have never thought of his clever creation, no matter how long I lived in the apartment. But because of his skills, turning the attic into a loft was an obvious decision. 

Study a panoramic idea for long enough and you’ll start to see its effects everywhere. People with intimate knowledge of One Big Idea monopolize a narrow band of the light spectrum, which gives them access to ideas and opportunities regular people miss. Like Nick, you’ll have the kind of realizations that seem amazing to others, but obvious to you.

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My One Big Idea 

Everybody has a worldview, a unique way of looking at the world. There is no such thing as pure objectivity. The world is pregnant with opportunities, which reveal themselves to us once we decide how we want to see. Building a worldview seems constraining at first. Why would you limit yourself to a small set of ideas? In reality, doubling down on One Big Idea is like walking through a portal into a vast, panoramic space you couldn’t have imagined. It’s the same story we see in movies, from Platform 9 3/4 in Harry Potter, to the rabbit hole in Alice in Wonderland, to the wardrobe at Professor Kirke’s House in The Chronicles of Narnia which is a door into the limitless world of Narnia. 

David Foster Wallace spoke about worship in his famous 2005 speech called This is Water, and the idea applies equally to building a worldview:

“In the day-to day trenches of adult life, there is actually no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship.”

If we are destined to follow the compass of our worldview, we should design it deliberately. Like Rich Barton and Richard Mosse, both of whom got rich pursuing One Big Idea, we should look for a panoramic framework to interpret the world through. 

As for me, I’m still developing my One Big Idea. For now, I’ve sunk my teeth into the belief that people systematically under-estimate the scale and interconnectedness of the Internet. I first discovered the idea in college, when I received my first job from Twitter and skipped college classes because learning on the Internet was faster and more enjoyable. Those experiences led me to start Write of Passage, an online writing school where students learn how to build their audience, make friends on the Internet, and improve the quality of their writing. All my thinking orbits the central idea of the internet’s impact on learning, entrepreneurship, and personal relationships. 

In my pursuit, I’m guided by the famous words of Bruce Lee: “I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.” 

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Cover Photo Source: Daniel Mosse’s Incoming

This essay was written with Ellen Fishbein, my writing coach.

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Pseudonyms are coming back.

The most interesting articles I read and Twitter accounts I follow are increasingly penned by pseudonymous authors. People like Jesse Livermore, Modest Proposal, and The Stoic Emperor can avoid ridicule and pursue unpopular ideas because they aren’t paralyzed by the social repercussions of their words. With the assurance that old thoughts won’t come back to haunt you some day, you can write freely about controversial ideas, difficult experiences with friends, and work-related observations that might upset your employer. Stripped from the chains of risk, writing will become easier because you won’t need to hold back.

Writing online brings social and financial benefits. But the social risks of online harassment or rejection from your social circle are too high for many people to start. Thus, our culture is riddled with “Don’t Post on Facebook” syndrome, where many of the smartest people don’t publish online for fear of unexpected and career-ending consequences. Specifically, people are afraid of instant repercussions from their employers, their friends, and the media-at-large. A friend recently told me he received backlash from his company’s public relations department for telling the honest story of co-founding his company and revealing some of its financial numbers. 

Many other hyper-intelligent people won’t publish anything work-related for fear of losing their jobs. The more people pay attention to them, the less they can say. They see other online writers succeed and believe they could have the same success if only they could write under their real name. Those who sit on the sidelines and consume without producing content underestimate the benefits of writing under a pseudonym, even if you only have a niche audience and 3-5 well-written essays on your personal website. By writing under a pseudonym, they can avoid compliance issues at work and skirt the troubles of Internet fame. The more a topic challenges the predominant narrative of society, the more likely the best accounts who write on that topic will be pseudonymous. 

Balaji Srinivasan, the former Chief Technology Officer at Coinbase has said: “Over time, doing things under your real name on the internet will be a bit like putting your social security number out there. It won’t commonly be done. Instead, people will earn and speak under different pseudonyms. Real names and Social Security Numbers will be confined to official forms.”

As pseudonyms become more common, people will separate their social name from their earning name so their words don’t destroy their economic opportunities. Moreover, sharing ideas that are mainstream in the moment can come back to bite you a decade later when consensus shifts and the values of the future conflict with the moral code of the present. Because anonymity protects them from the risks of publishing online, people who write under a pseudonym can pursue the truth without fear of punishment.

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Old-Time Pseudonyms

The cultural effects of the Internet may be new, but writing under a pseudonym isn’t. Many of America’s forefathers wrote under pen names. By obscuring their identity, the forefathers could share clever ideas without the risk of libel or sedition charges. The impressive list of names who wrote pseudonymously includes Thomas Paine, Alexander Hamilton, Tomas Jefferson, James Madison, and Benjamin Franklin. 

Franklin wrote under the pseudonym Ms. Silence Dogood to publish work in the New-England Courant. At the age of 16, Franklin was working for his older brother who wouldn’t let him publish his ideas. But by creating the alter-ego and dropping the letters under the door of his brother’s print shop every week, Franklin saw his ideas in print. Using the pseudonym, Franklin critiqued life in colonial America. He used a satirical tone which contrasted the era’s rigid and conservative social mores. The character he created with a pseudonym was so appealing that he received letters from men offering to marry “Ms. Dogood” once they learned she was widowed. Later on, Franklin wrote under the pseudonyms of Richard Saunders and Poor Richard in Poor Richard’s Almanack. There, Franklin wrote with his characteristic blend of thrift and courtesy. 

In addition to protecting his identity, writing under a pseudonym forced Ben Franklin to pursue an extra layer of truth. As I wrote in the Social Media Trap: 

“On social media, we create our own Big Brother. The laid-back honesty users once had when posting on Instagram and Twitter in the platforms’ early days is gone now. Spend enough time on both platforms, and you’ll begin to operate with the tact of a corporate communications professional. Both platforms are performative. On Instagram, we judge every post by its impact on our public image, and on Twitter, we have to examine how our ideas will be interpreted by a wide range of audiences — today and in the future — with permanent records of everything we publish. Now that our failures are on public display, we’ve stopped taking risks.” 

Freed from the Social Media Trap, pseudonymous writers can write like scientists instead of public relations professionals. With their identity obscured, writers enter an idea meritocracy where they can’t get away with hollow arguments by appealing to authority. Likewise, their readers can’t make ad hominem attacks — where they criticize the writer’s identity instead of their ideas. Given these limits, merit and truth become the most important factors in the fight for truth, which raises the quality of public discourse. 

Beyond the Founding Fathers, the list of famous writers who wrote under pseudonyms includes C.S. Lewis, Isaac Asimov, J.K. Rowling, Michael Crichton, and Stephen King. 

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You Keep the Benefits of Pseudonymity

People who write under a pseudonym can still access the benefits of writing online — such as access to people, ideas, and opportunities — whether they reveal their identity or not. 

Writers who remain behind a curtain of pseudonymity can still watch their ideas spread. For example, people like Modest Proposal and Jesse Livermore are still invited on popular podcasts like Invest Like the Best and quoted by big-name writers like Ben Thompson. The allure of mystery can be a tailwind too. I’m surprised by how many impressive people large, pseudonymous accounts have been able to meet without revealing their identities. Their emails and direct messages are filled with ultra-successful people who use their influence to persuade them to reveal their identity or meet in person. 

Others build their audiences before they reveal their identity. Michael Mayer, who used to write exclusively behind a pseudonym, shared his strategy for converting his pseudonymous following into real-world money and friendships in an interview with Patrick O’Shaughnessy. Even if you hide your identity behind a pseudonym, you can still use email and direct messages to make friends, fundraise for your business, or develop an online product. In that way, writing under a pseudonym is like a call option. You can postpone your decision to write under your real-name without repercussions.  Here’s Michael Mayer:

“It’s somewhat easy to transfer that social capital to the right places when necessary. It’s somewhat overrated to accumulate social capital only under your own name. I still have control of the various accounts I have, and they’re still my own capital. It’s like a Swiss bank account. I can transfer out of it whenever I want.”

Michael used his online audience to attract employees, customers, and investment dollars for his startup called Bottomless. In fact, I’m a customer because I’m such a big fan of Michael’s Twitter account and want to support his business. 

Likewise, Dan McMurtie, the founder and CEO of Tyro Partners, wrote under the pseudonym SuperMugatu for years. Using the pseudonym, he built connections with higher-ups in the financial industry. One day, he direct-messaged me on Twitter to speak about writing, and, impressed by his 25,000 Twitter followers, I responded right away. Like Michael, Dan made a business decision to start writing under his real name instead of his pseudonym after writing a viral essay on the dating market. Now, he’s being interviewed on Real Vision and featured on Bloomberg podcasts.

As demonstrated by the stories of Michael and Dan, if you want to transfer out of your pseudonym and start writing under your real-name or use your pseudonym’s capital for your real identity, you can. Sure, there are some risks to writing pseudonymously. I wouldn’t be able to teach Write of Passage under a pseudonym because effective teaching requires face-to-face interaction. But I could sell an app or a product under a pseudonym. For example, Wall Street Playboys and Overheard in the Goldman Sachs Elevator have built six-figure online businesses without ever revealing their identities. 

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The Components of a Good Pseudonymous Brand

The most popular pseudonyms tend to have two things in common: (1) They create a character, and (2) they take a stand. 

1. Create a Character

I recommend using a face, not a logo, for your social media profile picture. Something like a statue of a Greek king or a portrait from a famous painting. My reasoning is simple: It’s easier for people to connect with faces than logos, which will make your account more memorable. Once you’ve made the character, run with it. Create slang, patterns of speech, and jokes that align with your character to amplify the energy of your words. 

Build a world with your character that goes beyond the ideas you share. Outside the pseudonymous world, Nassim Taleb is a master at character building. In his books, he uses a character named Fat Tony who is a careless and shrewd Italian, who grew up in Brooklyn, and now lives in New Jersey. Fat Tony has working-class speech patterns and deadlifts every day, but only in gyms that cost less than $10/month with the first month free. 

On Twitter, the Stoic Emperor has done an excellent job building mystery and capturing the allure of ancient Stoic wisdom. Their beard and shadow in the profile picture communicate the wisdom of an old soul, and the cover photo at the top refers to ancient Greece. The location has been changed to “The Inner Citadel,” which hints at the headspace of philosopher-king Stoics like Marcus Aurelius. 

2. Take a Stand

The algorithmic lords reward people with loud opinions. Because the Internet makes it so easy to find people with fringe opinions and unconventional value systems, differentiation is free marketing. The most popular accounts create a movement around their ideas because they say things you won’t find elsewhere, in ways nobody else will say them. 

Here, Carnivore Aurelius has drafted the blueprint for future creators. The account blends diet and practical philosophy into a cocktail of ideas you won’t find anywhere else. Two slogans, “Take Back Control” and “Comfort is the Worst Addiction,” steer its rhetorical ship. It rebels against the standard American diet and the food pyramid that justifies it. It’s a crusade against a culture of sloth and a celebration of personal responsibility. By presenting strong opinions with science to back up the claims, the account has built a following of 56,300 people in 16 months and reached cultural influencers like Joe Rogan. 

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The Pseudonymous Billionaire

Beyond the world of online writing, the Bitcoin white paper was written under the pseudonym, Satoshi Nakamoto. More than a decade later, nobody knows who wrote it and Satoshi is worth billions of dollars. True to the promise of pseudonymity, the ideas have transcended identity. In contrast to a figure like Elon Musk who can be the subject of a federal investigation or who can attract ridicule by smoking weed on a podcast, Satoshi’s identity cannot be touched. To the Bitcoin community, Satoshi has become a god-like founding figure for people to rally around. The untouchable Satoshi narrative is one of Bitcoin’s greatest assets. People care about Satoshi’s ideas, not his credentials. Regardless of Bitcoin’s long-term prospects, Satoshi’s legacy teaches us that you can write under a pseudonym, and still become a billionaire while transforming the global monetary system. 

We have seen too many celebrities spend years growing their reputation, only to have their goodwill collapse in a media firestorm. Legions of pseudonymous writers will rise up in response. Those who build a character and take a stand will force people to associate with their ideas instead of their identities and their message instead of the messenger behind it. In turn, the Internet will transfer social capital from the well-credentialed few atop the ivory tower to armies of self-educated writers who demonstrate knowledge by publishing their ideas and building an online audience. 

Pseudonymous influencers are here to stay. 

“The Singularity Is Near.”

These are the famous words of Ray Kurzweil, who predicted a coming moment when technology would become so advanced that society would experience irreversible change. He predicted that by 2029, an Artificial Intelligence will pass a Turing test and achieve human levels of intelligence. Propelled by Moore’s Law, he thinks the “singularity” will arrive in 2045 when computers are one billion times smarter than humans.

The Oxford Dictionary defines the Singularity as “A hypothetical moment in time when artificial intelligence and other technologies have become so advanced that humanity undergoes a dramatic and irreversible change.” But if you remove artificial intelligence from the definition and focus on “dramatic and irreversible change,” the singularity is already here.

It began during the Industrial Revolution, when mass-production kicked into high gear and initiated the largest wealth creation boom in human history. According to economist Brad DeLong, “World GDP per capita hovered around 90-200 from ancient times up through 1800, then jumped to 300 by 1850, 679 by 1900, and up to 6,539 by 2000.” The increases in GDP were paralleled by rising life expectancy, falling poverty rates, increased energy efficiency, war-making capacity, and the rise of democratic regimes.

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The Beginning of the Industrial Revolution

Singularities begin at the flip of a switch. One moment you’re outside of it, the next you’re swimming with the tide of its all-encompassing vortex. Once a Singularity picks up enough momentum, it becomes a black hole and absorbs everything around it. The Singularity we inhabit began at the start of the Industrial Revolution.

Here’s my thesis: The Singularity is already here, and it began in Western Europe at the end of the 16th century. Technologies like literacy and commercial law laid the foundations for the Singularity, but the early industrialization process began with an order of magnitude improvement in land transportation costs. Until then, moving goods and people over land was expensive. The Dutch East India Company may have sailed from Holland to India and discovered Manhattan in 1609, but before the improvements in transportation around the time of the Industrial Revolution, those distances were impossible to make on foot. Economic growth was nearly impossible because markets were so narrow and human action was so local. Even in the early parts of the 20th century, Chinese villages which were only five miles apart spoke in radically different dialects. Without efficient transportation, people were trapped in poverty and unable to benefit from trade.

In an excellent series of essays (including this essay and this other one as well), Nick Szabo shows that small decreases in transportation costs led to large economic improvements. Specifically, Szabo credits horses, steam engines, and steam-powered railroads for the series of wealth-creating inflection points. I’ll take each in turn.

Work horses increased labor productivity and expanded the amount of land farmers could cultivate, thereby initiating another productivity-improving enhancement of agricultural specialization. The replacement of oxen with horses further improved transportation speeds, which doubled the speed of transporting a wagon of goods. With steam engines, industrial machinery no longer ran on horse gins or watermills. Finally, steam-powered railroads enabled bulk transportation and connected mines and factories with major cities. With all these improvements, humans relied on animals and machines instead of their own backs and biceps.

Why do transportation costs matter so much?

Szabo explains: “The potential value of a land transportation network is the inverse fourth power of the cost of that transportation. A reduction in transportation costs in a trade network by a factor of two increases the potential value of that network by a factor of sixteen. While a power of exactly 4.0 will usually be too high, due to redundancies, this does show how the cost of transportation can have a radical nonlinear impact on the value of the trade networks it enables.”

Transportation costs are the primary constraint on the size of the market. As they fall, trade flows increase and enable the wealth-creating division of labor system first outlined by Adam Smith. Recent empirical data confirms Smith’s hypothesis. This study of the American highway system found that a 1% reduction in the travel distance between two trading partners increases trade between them by 1.4%.

True to the singularity thesis, dramatic improvements in transportation efficiency brings compounding benefits. Specifically, falling transportation costs lead to increased innovation, and increased innovation leads to falling transportation costs, thereby initiating a virtuous cycle of increased trade and globalization.

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The Technological Singularity Is Already Here

The Industrial Age touched every aspect of the Western world. The forward process in quantifiable living standard kickstarted a Singularity, the evidence for which we see in the evolution of global markets, systems of governance, and the dizzying speed of technological advancement. For the purposes of this essay, I’ll focus on technology.

We used to build technology to solve well-defined problems in service of a well-defined future. But today, we tend to build technology aimlessly without a plan for the future.¹ Some define progress as “more technology,” so we develop new technologies before we think about how they will impact us. For an example, look no further than Facebook. In less than 15 years, the company that began as a rating system for hot girls at Harvard unexpectedly became the epicenter of global communication as society became more globalized.

Moreover, you can’t opt out of technology even if you try. Marshall McLuhan once said: “First we shape our tools. Then our tools shape us.” Say you want to avoid using a car. On Sunday mornings, you used to walk to church to see their friends after the service, shop at the local farmer’s market together, and walk home with food for the next 48 hours. But with the invention of the car, small local churches become mega-churches next to a highway and local farmers markets that used to be within walking distance become a strip mall Walmart that only a car can get you to.

As technology wraps its fingers around society, you either have to farm all your own food or cave to the demands of the technological singularity. Additionally, the World Health Organization reports that almost 1.35 million people die in road crashes every year. And yet, we let the car dominate American life without questioning its side effects. When an accident happens, we blame drugs, sleepiness, alcohol, the weather, or faulty car designs instead of the use of the car itself. But in parallel with the logic of a singularity, people like Nick Land and Peter Thiel argue that accelerating the pace of technological progress is the only peaceful path forward.

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Will the Singularity Continue?

We have already achieved a singularity. Those early transportation-inspired improvements at the beginning of the Industrial Revolution initiated the gradual dominance of markets, democracy, and technology. Of the three, I have the most faith that markets and technology will continue to dominate, but I’m less confident about the future dominance of democracy.

Regardless, we can’t go back to the future. We have already met the singularity state of irreversible momentum — where technologies such as cars, computers, and nuclear weapons govern us more than we govern them.

Kurzweil predicted that the Singularity was near. But it turns out, the Singularity is already here.

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Footnotes

¹ Here is the wrinkle in my Singularity thesis: The Industrial Singularity followed an S-Curve, not an infinite exponential curve. Economists like Robert Gordon and Tyler Cowen argue that economic growth began to slow in the 1970s. If the singularity is going to end, we already see evidence in the pace of technological development in the physical world. In New York, for example, we haven’t built a new bridge since 1964 and three new stations on the Second Avenue Subway line took 17 years to build.