I was a terrible writer growing up. I got a C- in my college writing class. At one point that semester, I skipped ten of those classes in a row because I didn’t see the value in learning to write. When I told my high school writing teacher that I’d taught thousands of people to write online, she spit out her drink because she thought I was joking.
If I didn’t grow up with the passion to write, where did it come from?
I started writing because I was jobless and needed to turn my life around. I was an over-saturated news consumer with nothing to show for it. I loved ideas, but had nobody to discuss them with. When I brought up intellectual subjects, my friends mocked me.
I was unemployed, overstimulated, and unfulfilled.
Desperate for a solution, I started writing online. At the time, I was nameless and stuck on the sidelines because I didn’t have the gumption to share my ideas. I experienced a cocktail of searing emotions — envy, inspiration, fear, curiosity, rage, hope, hopelessness, excitement, and self-loathing. But with each article, things got a little better. For the first time in my life, I made use of the information I consumed. The friends I made shared my obsession with ideas. As I published, I realized that everything I wrote was a magnet to attract opportunities that felt like magic in the moment, such as a $20,000 grant and a podcast interview with Neil deGrasse Tyson, arguably the world’s most famous scientist.
Five years later, I can say that writing on the Internet is among the best life decisions I’ve made. The 90 minutes I spend writing every morning is my most important habit and the activation code for just about everything good that happens to me. For years, I thought that being successful and being myself were diametrically opposed, but becoming an online writer has shown me that I can succeed by bringing out more of myself — and so can you.
Writing gave me wings. It unlocked the latent potential of the Internet. You can access humanity’s best thinking, improve your own, and freely share your best ideas with a global audience. The writer’s path is no longer reserved for authors, journalists, or your aunt’s crazy Facebook rants. Anybody can walk it now.
My life is devoted to helping people write online. In Write of Passage, I teach a proven system that’s built for the 21st century. Our alumni base includes some of the fastest-growing online writers in the world right now (such as Packy McCormick and Ana Lorena Fabrega). I’ve distilled the most important principles from the course into this guide.
- Writing from Abundance is the art of collecting ideas so you can think better and avoid writer’s block.
- Writing from Conversation is the art of using dialogue to identify your best ideas and double down on them.
- Writing in Public is the art of broadcasting your ideas to the Internet so you become a beacon for people, opportunities, and serendipity.
The game of online writing rewards people who publish consistently. Though frequency is the price of entry, quality writing is a force multiplier on your success. If your ideas resonate, the number of opportunities available to you will explode.
As you write, you’ll gain clarity around your Personal Monopoly — a unique online identity that emerges out of your skills, experience, and interests. As a compass, it’ll guide you towards the right people, meaningful work, and a life of freedom. By the end of this guide, you’ll have a roadmap for building one.
Now, I’m going to unpack what it takes to become a successful online writer.
DOWNLOAD YOUR PERSONAL MONOPOLY GUIDE
Become known as the best thinker on a topic and open yourself to the serendipity that makes writing online so special. Uncover your strengths, clearly communicate your values, and start building your reputation online. Download the guide to your Personal Monopoly.
Write from Abundance
My Struggle with Writer’s Block
I used to face crippling bouts of writer’s block. My mind would race with ideas when I was away from my desk, only to turn off whenever I sat down at my computer to write. I’d spend hours looking at my screen, only to get no writing done and leave with a blank page. It was infuriating.
Fortunately, my writer’s block disappeared once I started Writing from Abundance.
The premise is simple — build a bank of inspiration while you’re away from the computer and before you sit down to write. Capture your epiphanies. Save the best quotes you read. Identify ideas that resonate with you and jot them down as notes.
Writing from Abundance is the art of collecting ideas so you never have to write from scratch. It’s about living a life that brims with inspiration. That inspiration can come from external sources—like social media, articles, or books. It can also come from internal sources–like dinner parties, work meetings, or shower thoughts. If you capture ideas when they’re in the forefront of your mind, you won’t have to pray for them to come back when it’s time to write.
Once I learned to Write from Abundance, I saw how the practice was alive in many fields. I last saw them when I visited my tailor and asked him for help making a blazer. Instead of starting from scratch, he put a bunch of materials on the table (silk, buttons, swatches, etc.). Then he mixed and matched the possibilities until a design emerged. Your notes are like those raw materials. If you ever get stuck, you can pour them onto the page and see what materializes when your ideas collide.
In order to start Writing from Abundance, there are three things you must do:
- Upgrade your Information Diet
- Practice the Capture Habit
- Build a Note-Taking System
1. Upgrade Your Information Diet
FIND BETTER INGREDIENTS
Most people don’t use the Internet to learn. They use it to follow pop culture and keep up with their friends. Neither of these strategies are very effective for having better ideas.
Every great writer I know obsessively curates their information diet. They rightfully know that high-quality writing begins with good taste for what you consume. Writing is like cooking. If you walk into a Michelin Star restaurant and ask the chef: “What’s the fastest way to improve the quality of your food?” they’ll likely say: “Better ingredients.” At the end of the day, heaps of dressing can’t make up for stale lettuce. A salad can only be as good as the fruits and vegetables inside of it. Your experiences, conversations, and information sources contain the raw ingredients for your writing.
It’s easier to have unique ideas when you read things other people don’t. Early in his career, Warren Buffett got some of his edge by going beyond the Annual Reports that everybody else was reading and picking up 10-K filings that were tough to get your hands on back then. David Epstein aims to read ten journal articles per day when he’s working on a book. Many of his best ideas come from reading papers that others won’t and synthesizing them for a public audience.
Beware of too much news consumption. Yes, it’s good to be an informed citizen. But the idea that obsessively reading the news is the best way to stay informed is a lie sold to us by the propaganda machine. Most news is inconsequential. It’s entertainment dressed as information. Though it can be good to have a general sense of what’s happening in society, you probably don’t need to be plugged into a 24/7 stream of news — or what I call: the Never-Ending Now.
ESCAPE THE NEVER-ENDING NOW
I once attended a comedy show with a group of friends. Since the venue was across town, we split a Chevy Suburban SUV. From the moment the driver hit the gas, everybody was on their phones. From the back row, I watched my friends scroll their social media feeds with ferocious intensity. One thing stuck out: everybody in front of me only consumed content created within the last 24 hours.
I succumb to the same impulse. Chances are, so do you. Like hamsters running on a wheel, we live in an endless cycle of ephemeral content consumption — a merry-go-round that spins faster and faster but barely goes anywhere. The Internet is a novelty machine that pulls us away from age-old wisdom. Even though we’re just a click away from the greatest authors of all time, from Plato to Tolstoy, we default to novelty instead of timelessness.
We’re trapped in a Never-Ending Now — blind to history, engulfed in the present moment, overwhelmed by the slightest breeze of chaos. Here’s the bottom line: you should prioritize the accumulated wisdom of humanity over what’s trending on Twitter.
If you need timeless recommendations, I’ve spent the past five years collecting some for you.
CURATE YOUR INFORMATION STREAMS
How can you upgrade your information diet?
- Short-form: Social media is at its best when it matches you with people who share your exact interests and teach you about what you want to write about. Unfollow celebrities. Replace them with people who make you smarter and bring long-lasting joy.
- Medium-form: Read less of the news. Subscribe to magazines and YouTube channels that post timeless ideas. Read essays and speeches that have stood the test of time. Find people whose recommendations you consistently enjoy and subscribe to their newsletters.
- Long-form: Get away from your screen and read more books. If it helps, start a book club. Find classic books to read. Watch old documentaries and listen to lecture series. Crawl the Internet for college syllabuses so you can read them on your own time.
2. Practice the Capture Habit
Now that your incoming information is solid, you need a way to harness it. It’s not enough just to binge eBooks and list a stat on your website (one Write of Passage student refers to this as “Book Chugging.”) You should save the best parts of what you read, so you can easily reference them later.
By capturing ideas in the moment, you can effectively start essays when they’re 80% finished.
Notes are so central to my writing process that writing without them is like building a campfire without a pile of wood. Because I’m so diligent about writing ideas down, I don’t need to run back to the “forest” every time I get stuck. Instead of starting a new research process for each new article, I pull from ideas I’ve already captured in my casual reading, from conversations, and from the ordinary moments of my life. All those notes became intellectual fodder for future pieces.
I call this process “Ambient Research.” By the time I sit down to write about a topic, I’ve already done most of the research I need to write about it.
This method of Ambient Research is the opposite of what I learned in school. My teachers promoted Active Research, which led me to spend hours reading in the library after I picked a topic. Without notes to build upon, I had to start from scratch whenever I began an essay. Since I’m a slow reader, I had to give up my weekends for research.
Being a writer doesn’t mean you have to sacrifice huge swaths of your life. You don’t need to bunker down in a library for days straight in order to find inspiration. You already consume media, have thoughts, and write ideas in group chats. When you practice the habit of capturing what’s already happening, you’ll find that you have all the material you need to start writing.
Effective ambient research happens when you capture the best ideas you consume, the epiphanies you have, and the things you’ve already written to friends and colleagues. I’ll focus on each in the next three sections.
SET UP ‘READ-IT LATER’ APPS
Have you ever had that feeling where you have like 200 tabs open on your browser, but you don’t want to close them because you’ll lose such valuable articles that you intend to read? I’ve felt that anxiety. Luckily, there’s a solution: Read-it-Later apps.
I never read articles in my web browser. When I come across an interesting article, I save it to an app that automatically downloads it to my phone so I can read it later. Saving these articles gets me out of a reactivity loop, where I read things immediately after I find them (which is what most people do). I want my reading to be much more intentional than that.
Read-it-Later apps act as a quality filter for your reading too. By saving articles to an app and refusing to instantly read things you come across on the Internet, you raise the bar for what grabs your attention. With a Read-it-Later app, whenever you sit down to read, you have hundreds of articles to choose from. You can allocate your attention to the best one.
Using a Read-it-Later app showed me how many ideas I consumed not because they were important, but because it was marketed with “You have to read this!!!!” language.
CAPTURE YOUR OWN IDEAS
Do you ever forget ideas? Maybe you forget to write down an insight from a buzzing conversation with a friend, and two months later, when somebody asks you about what you discussed, you don’t remember zilch.
The same thing used to happen to me while traveling. I’d have tons of epiphanies while walking through a new city, only to forget them once I returned home. These impressions and emotions were unique to me. No Internet search could have yielded them. Now, they’re lost to the entropy of time. The clarity of memory decays quickly, so we shouldn’t just save other people’s ideas. We should save our own ideas too. Until we have a central place to capture our best thinking, the joy of epiphany will turn into the anxiety of forgetfulness.
Many of your unique and provocative ideas will come when you’re away from the computer — doing chores, driving around, or walking through your neighborhood. Ideas are fickle. That’s why so many of history’s greatest writers have walked around with a notepad. When I read about the writing processes of historians, they repeatedly talk about how they capture their impressions immediately after an interview ends, while their memories are still sharp. They know that ideas that seem obvious in the moment will be forgotten by the time they’re ready to write about them. Following their lead, whenever I have an important idea, I assume I won’t remember it and write it down as soon as possible.
Note-taking is the closest thing we have to time travel. It’s rebellion against the entropy of memory. Kendrick Lamar insists that much of the “writing” for his lyrics happens in the note-taking process. In one interview, he said: “I have to write them down and then five or three months later, I have to find that same emotion that I felt when I was inspired by it, so I have to dig deep to see what triggered the idea… It comes back because I have key little words that make me realize the exact emotion which drew the inspiration.”
Your ability to transcribe an event is better than your ability to remember it. Writing down your observations makes you more observant, and once you commit to capturing them, your brain generates more of them. It’s like photography. Putting a camera in your hands turns every moment into a photo opportunity, which makes you more aware of your surroundings.
NOTICE WHERE YOU ALREADY WRITE
I have a friend who writes long and incredibly well thought-out messages in group chats, but says she can’t find the time to write. Her diagnosis is wrong though. The problem isn’t that she lacks time. It’s that she doesn’t realize how much she’s already writing. Context determines her capacity for creativity. She has no trouble writing something substantial to friends, but freaks herself out whenever it’s time to write for an audience of strangers on the Internet. She’s a keyboard warrior in group chats, and the more she can realize how brilliant her ideas already are, the easier it will be for her to share ideas in public.
Likewise, I often find that I’ve written parts of my piece without realizing it, either in emails to friends or Slack messages to colleagues. Sometimes, I’ll even search my tweet history. I’ve made a habit out of saving anything substantial I write to a central note-taking system so I can easily retrieve it in the future.
If you’re stuck on writing, look back at what you’ve already written for inspiration– emails, texts, tweets, group chats, and Slack Messages. Ask yourself: “Where have I been writing all along?”
Chances are, you’re already generating ideas. You just don’t realize it yet.
3. Build a Note-Taking System
Where are your notes from college? If you’re like me, you basically threw all your binders into a massive bonfire after the semester ended. Now, you have no way to find the best ideas you came across in school. Even if you magically found them, your notes would be scattered all over the places in random binders and notebooks.
The brain is great at creating connections, but terrible at remembering specific details (which is what computers are uniquely good at). Note-taking works best when the ideas are saved in a central location that contains the best reading and thinking you’ve ever done. The easier it is to search those notes, the faster you’ll be able to find them.
You don’t need the perfect note-taking system though. It can be chaotic and disorganized, and as messy as your high school bedroom. Though note-taking has been transformative for many writers, it’s telling that none of the best writers I know have a perfect note-taking system. They make something that works (even if it’s duct-taped together), and get on with what’s important: actually writing.
James Clear, who wrote the wildly popular Atomic Habits, keeps his notes in a massive, multi-hundred page Google Doc. Even Eminem, who sees note-taking as a way of “stacking ammunition” for his lyrics, packs words and phrases into a box with all kinds of folded and crumpled up paper.
There are tons of note-taking apps: Notion, Obsidian, Roam Research, Evernote. I don’t care which one you use. No matter which option you choose, remember that the point of taking notes is to write, not to have the perfect note-taking system.
I swear. There are people who put as much effort into their note-taking system as NASA engineers put into the rockets that got us to the moon. They spend so much time building the perfect system that they forget to actually write. Don’t do that. Note-taking is, literally, not rocket science.
If you’re just starting out, it might help to think of your note-taking system in two halves. First you collect the dots by capturing ideas, then, you connect them by writing.
COLLECT THE DOTS
Do you ever come across an exceptional tweet and feel like you need to save it? How about a fascinating paragraph that you’ll want to reference in the future? Both are worth capturing in a central location that you can easily flip through later.
Study the writing practices of history’s top writers and you may be surprised by how many kept a commonplace book. A commonplace book is a central place where you can save ideas, quotes, epiphanies, photos, drawings, and whatever else you want to remember. Marcus Aurelius, the former emperor of Rome, used his commonplace book to write Meditations; Montaigne, who basically invented the essay format, kept one; so did Napoleon, HL Mencken, and Thomas Jefferson.
Since most of your ideas will arise when you’re away from the computer, capturing ideas should be frictionless. You should be able to write an idea down within 10 seconds of having it. If writing a note takes too long, you won’t write the good ones down, and eventually, you’ll forget your best ones.
You should be able to instantly capture ideas while reading too. There are several ways to do this, but Readwise provides the most elegant solution. Everytime you highlight in Kindle or on Instapaper, and everytime you bookmark a tweet, it shoots that information into a central repository where it’ll live until the messiah returns or the heat death of the universe.
If the search function on your note-taking app is powerful, you don’t need to spend much time organizing ideas. You can throw a bunch of quotes and hunches and statistics and graphs and photos and rants into a single location, knowing that you’ll be able to find them later. Over time, you’ll develop a personal Google search engine. But unlike the actual Google, you’ll have pre-vetted everything inside of it and you’ll serendipitously stumble upon ideas you forgot you’d ever seen.
So long as (1) you can capture ideas quickly, and (2) all those ideas go into the same place, you’re setting yourself up to Write from Abundance. It doesn’t really matter what note-taking app you use.
CONNECT THE DOTS
Once you’ve built a simple and low-friction way to collect the dots, it’s time to connect them. Little-by-little, you’ve been planting seeds. Writing from Abundance is how you harvest all the little fruits you’ve sown. Jimmy Soni, who wrote The Founders, told me that he started the writing process for every chapter by dumping his notes on the screen and seeing what emerged. For him, it was so much harder to write from a blank page than 10,000 words worth of facts, quotes, and anecdotes.
His method reminds me of a line from Michelangelo, who said: “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.”
I start my essays in split-screen mode. On the left side of the screen, I have my notes. On the right, my blank document. To fill up the blank page and give myself momentum, I’ll run a few searches through my note-taking system, and copy & paste the best stuff onto my new essay document. As I add ideas to the document, patterns emerge which become the structure of the piece. Usually, the piece’s structure organically emerges, as if I’m being guided by an invisible muse. What was recently just a bunch of messy ideas in my note-taking system turns into a structured outline. All I need to do is fill in the gaps, add transitions between ideas, and rewrite the prose until it reflects my best thinking on the subject.
It’s worth spending some up-front time to build a note-taking system. But remember, it doesn’t need to be fancy. Mine is a mess. Once you have an easy system for adding and searching ideas in a single location, it’s time to write. Gone goes the blank white page of doom. Now, when you sit down to write, you’ll instantly be able to draw from the best ideas you’ve ever had.
Write from Conversation
Writing Doesn’t Need to Be So Lonely
When most people think of writing, they think they need a weekend retreat to escape society. They imagine the writer as a lone genius crafting their magnum opus in a backwoods cabin with shoddy plumbing. In an existence of pings and obligations, it’s natural to think that isolation is the only way to focus. Maybe this works for veteran novelists, but not for online writers.
You don’t need to do it alone. In fact, being in conversation will make you a better writer. Humans are not fully autonomous thinkers; we are social beings. Conversations let us identify high-potential ideas and tweak their delivery until they represent our best thinking on a subject. My ideas took on a new level of refinement once I started Writing from Conversation.
The concept may be new, but the method is centuries old. The Bible was spoken long before it was ever written. So were most Greek tragedies. More recently, Ralph Waldo Emerson, one of the top writers of the 19th century, developed his famous essays through public lectures. When lectures like The American Scholar resonated with the audience, he published them in writing.
In so many areas, from design, to startups, to relationships — improvement comes from feedback. When you’re so close to an idea, you’re victim to your own blindspots. Instead of assuming what’s good, conversations prove it. Before you sit down to write, you can test your ideas in conversation.
The gift of the Internet is that it lets us test ideas at scale. In this section, I’m going to show you how to do that. I’ll start by showing you how ideas develop: first, with friends; then with readers; and finally, with editors. Each phase helps you refine your ideas. What begins as messy notes get distilled into memorable phrases that’ll ring in your readers’ mind long after they’ve finished your piece.
This process of distillation begins with the Content Triangle.
The Content Triangle
Many writers suffer from perfectionism, where they refuse to share ideas until they’re perfect. Perfectionism is particularly pernicious because it’s a vice that looks like a virtue. It’s the child of two parents: fear and narcissism. It’s dangerous because you can rationalize away your fears with the excuse that your standards are higher than everybody else’s.
To shake the temptations of perfectionism, I share half-baked ideas all the time. Doing so helps my writing because I can run ideas through numerous filters, such as blogs, tweets, and email newsletters. By the time I’ve published an essay like this one, I’ve run the ideas through various forms of low-cost, high-speed trial-and-error. Each time I receive feedback, I keep more of what resonates and less of what doesn’t.
I call this method of refining ideas through a series of escalating social filters “The Content Triangle.”
The Content Triangle is embedded into the world of comedy too. I once lived with a comic who basically tested his stand-up routine on me every night. Turns out, he wasn’t the only one. Comedians are always testing jokes with friends and small audiences before they film their Netflix special. Chris Rock once said: “When I start a tour, it’s not like I start out in arenas. Before this last tour, I performed in this place in New Brunswick called the Stress Factory. I did about 40 or 50 shows getting ready for the tour.”
The standup special you see on Netflix is nothing like the first cut. In comedy, as in writing, you don’t see all the work it takes to make something great. You don’t see the 50 performances he gave at small comedy clubs around the country, and you certainly don’t see the jokes that bombed along the way.
You don’t have to be a comedian or professional lecturer to “write from conversation.” You’re having routine conversations all the time. Don’t discount the feedback you receive from them. Test your ideas out on intelligent friends. If an idea consistently surprises somebody, it’s probably good, but if people look bored or confused when you’re sharing an idea, you should either drop it or communicate the idea differently.
The Content Triangle is a method for developing ideas in various stages:
- Conversations with friends help us discover surprising ideas that are worth exploring.
- Conversations with readers tell us if an idea will resonate with our audience.
- Conversations with editors help us improve how our ideas are delivered.
I’ll explain each stage below.
4. Conversations With Friends
THE POWER OF SPEECH
Writing from Conversation piggybacks on the brain’s natural ability to compress ideas.
Speaking is the first draft of thought. I often struggle to structure ideas when I’m writing about them. But once I start to speak, words have a way of coming together. Saying something out-loud gives me an initial structure that I can refine in subsequent drafts. When I feel an idea emerging in my head, I often pull a voice-to-text transcription app to record my thoughts (I recommend Otter).
Speaking is good for generating ideas, and writing is how you perfect them. When you write in a text editor, you have the ability to pause, edit, and dwell on a sentence. Often you can get stuck on perfecting your introduction for an hour before you even get into the meat of your idea. Speaking out loud doesn’t let you stop. You can only move forward.
The power of speech is amplified through conversation. In conversation, your partner’s reactions can help you gauge the quality of what you’re saying. Sparring partners take you to the heart of an idea. They force us to distill ideas to their essence. We change our delivery based on who we’re speaking with too. Your ideas will be funnier if you’re yapping at the bar with your college buddies. If you’re at a crowded boardroom roundtable, you’re more likely to give a compressed elevator style pitch than a full lecture.
LOOK FOR SURPRISE
When you start exploring an idea, it sprawls all over the place. Like a college smoke session, you’re in the “dude, if you really think about it, everything is connected” phase. In truth, most of the ideas are fluff (like somebody who tells 15 minutes of backstory before the good stuff begins). Even if there’s a “woah” moment at the end, the boring backstory puts you to sleep before the punchline.
Skip the 12-minute rant. Test facets of your ideas (briefly) and observe the reactions. Conversations aren’t the place to explore every nuance, counterpoint, backstory, and implication of your idea.
Embrace the dance of conversation. Good conversations push the frontier of consciousness. Pick one small part of your idea and put it out there. Observe. Watch their body language as you speak. Notice the questions they ask and the assumptions they bring to the table. All those responses yield new information. You see the map of your idea through their eyes, which shapes your next move.
You can identify each emotion in conversation, based on people’s facial expressions: they raise their eyebrows when they’re confused, invite you to speed up when you’re repeating yourself, lean in when they’re interested, look away when they’re bored, and open their eyes when they’re surprised. If you can pay attention to how people respond in casual conversation, you can develop ideas before you put them on paper, which makes the writing process more efficient, effective, and enjoyable.
If their eyes widen, they let out a gasp, and go “whoa!”— jackpot. You’ve surprised them. You’ve found something worth building your essay around. Remember what you said and remember to write down exactly how you said it (if you’re fired up, sneaking off to the bathroom is the most socially acceptable way to take notes in the heat of conversation).
Surprise signals that someone’s mental model of the world has changed (AKA, you’ve blown their mind). It’s more than just learning a new fact. It’s the kind of epiphany that comes deep from left field and breaks your expectations. Sometimes we grow so familiar with ideas that we stop recognizing the surprise in them.
Optimizing for surprise means cutting out the filler and doubling-down on the parts of your idea that defy expectations.
WRITER BRAIN / FRIEND BRAIN
A serious advantage of writing from conversation is that you avoid “Writer Brain.” When you open a Google Doc (hint, doc.new), it’s easy to boot up the tedious writing patterns you picked up in school. You tense up. “Time to get serious,” you say. You become a risk averse, politically correct dweeb— and more status obsessed than Regina George in Mean Girls.
The rising costs of WrongThink leads to self-censorship when it’s time to write. For fear of cancellation, we lock away unpopular opinions. Gone go the flames of passion and the snarky one-liners. Writer Brain inevitably takes over, becoming a cock block that keeps our personality away from our ideas.
“Friend Brain” is our natural way of speaking. It comes easily to us in conversation, and it knows how to party. It’s the friend your Mom warned you about — the one who was super mischievous and high-agency and gave you that intrepid spirit.
Conversations with trusted friends awaken your primal nature. They’re arson for your scared and timid self — the weakling inside of you that cares too much about what other people think. Only with trusted friends can you speak with an unfiltered and passionate fury. Cry. Scream. Rile yourself up. Rant like a Jewish grandmother. And if you really need to, get whiskey drunk and see what spills out after drink #3. In these moments of sweltering honesty, once we’ve freed ourselves from a self-induced prison of the mind, we’re able to unleash brave and surprising ideas.
5. Conversations With Readers
TESTING IDEAS AT SCALE
Once an idea resonates in conversations with friends, it’s time to test it with your readers online. Before the Internet, your testing was limited to in-person social interactions. Never has it been so easy to be in constant conversation with people around the world who can respond directly to your ideas.
It can help to think of your writing like a tech company thinks about their product. Great products are spurred by tons of feedback. The same is true for writing. Conversations with readers make your ideas crisp and free you from the curse of knowledge. The Amateur’s Mind is one of the best books written about playing better chess. The author, Jeremy Silman, an International Master, spent a bunch of time speaking to amateur chess players about their challenges. Patterns emerged. Those conversations with readers helped him understand his readers and know what to write about.
Twitter and email are good places to share half-baked (but still edited) thoughts. Asking questions to your audience can work too. Done right, the feedback you receive can lead to interesting ideas you wouldn’t have found otherwise. If a response surprises you, it’ll probably surprise your readers too.
The sooner you receive feedback, the better. Conversations with readers are the way to determine which ideas are worth sculpting into full-fledged essays.
THE FEEDBACK-DRIVEN BOOK
I’ve never seen a non-fiction book pierce the winds of culture like James Clear’s Atomic Habits. He followed a feedback-driven writing process. He used Twitter to test his ideas. The engagement (or lack thereof) he received showed him when to double-down on an idea. Reader questions helped him find the best ways to articulate a concept.
His success points to a new paradigm in the way writers shape ideas. In the past, authors have developed their writing in private, only to share their magnum opus once it’s complete. Online writers are different. They share ideas with readers along the way. This dialogue has the twin benefit of helping authors refine their ideas while they build their audience. As I write this, Atomic Habits is the most popular non-fiction book on Amazon. In 2021, it was likely the best-selling book in the world.
Feedback-driven books are simply… better.
Until you develop a form of low-grade telepathy, your best bet is to cultivate feedback. By doing so, your writing will have less fat and a hell of a lot more meat on the bone. By the time you publish your book (or a long-form essay like this one), you’ll have gone through multiple cycles of the Content Triangle until each section has Idea-Market-Fit.
Though I recommend data-driven writing, it’s just a tool. Your intuition can be just as important as metrics from the market. While Twitter is a good place to test the popularity of an idea, it doesn’t exactly encourage thoughtful responses — which are more likely to arise via an email newsletter.
Many of my best essays have started by sharing embryo ideas in my newsletters and engaging in conversations with readers. I read every reply. Those replies highlight which ideas have legs and are worth pursuing. Sometimes, the responses catapult my writing on a new trajectory.
In one Monday Musings edition, I wrote about the commitment crisis. Time horizons are shortening and young careerists prefer optionality over-commitment. Towards the middle of the piece, I criticized them for “Hugging the X-Axis.” Multiple people said they resonated with the phrase. Those replies encouraged me to polish the idea and turn it into a full-fledged essay.
6. Conversations With Editors
HONEST, CRITICAL ADVICE
There’s a reason why professional writers with decades of experience use editors. No matter how good of a writer you are, you can’t see your blindspots. You’re simply too close to your ideas to know how certain parts of your essay land.
Chances are, your friends and coworkers aren’t interested in helping you rewrite sentences and shift around paragraphs. Nor do they have the courage to be blunt and say: “this part sucks.”
That’s what editors are for.
Once you’ve developed ideas with a crowd, it’s time to bring them to a small group of fellow craftsmen. You don’t need to pay a professional editor. Packy McCormick grew his audience to over 100,000 subscribers, and his editors were his brother and his wife (mine was the lady who still freaks out whenever I have a sore throat… thanks Mom!).
Your goal is to have a small network of trusted people who are good with words, willing to be honest with you, and want to see you succeed.
TYPES OF FEEDBACK
When you’re starting a conversation with an editor, it’s important to know which kind of feedback you’re looking for.
Types of feedback? What do you mean? Isn’t editing all about proof-reading?
Nope. In fact, software has gotten very good at editing. Tools like Grammarly and Hemingway have pole vaulted over primitive spell check.
But if you’re doing serious writing, it’s worth working with a human editor. Depending on what you’re struggling with, you can ask them for different kinds of feedback. Early in a piece, when you’re vomiting ideas onto the page, editors can help you identify what to focus on. They can also tell you if the piece is out of balance, like when you have a swarm of interesting observations but no personal stories to bring them to life.
In later phases, when the piece is coming together, it helps to get reactions from your editor. As they read, they can highlight sentences from your draft and share their feelings with you.
In Write of Passage, we use an acronym called CRIBS. Editors mark if a section is confusing, repetitive, interesting, surprising or boring. The method is universal because it focuses on standard emotions that everybody has instead of the mechanics of writing, which fewer people are familiar with.
Ask your editor to identify each letter in the CRIBS acronym, as explained below:
- Confusing: The more friction in the communication process, the harder it’ll be for an idea to get from the writer’s mind into the reader’s. Most of the time, when the reader is confused about what I’m trying to say, so is the writer.
- Repeated: Good writing is compressed. By definition, if you’re repeating yourself, your writing isn’t as tight as it could be. Compressed writing doesn’t mean short (just look at the length of this guide!). It just means that the pacing is brisk and each word serves a unique purpose. If people on the Internet always wanted the shortest thing they could find, Joe Rogan wouldn’t have the most popular podcast in the world.
- Interesting: A fraction of what you initially write will account for the majority of insight. Ask your editor to identify the most interesting parts of your writing, so you can double down on them.
- Boring: If a section causes your reader to lose interest, you need to change something. Remove the non-essential ideas. Rewrite the essential ones until they’re worthy of your readers’ attention.
- Surprising: This is the holy grail of quality writing because surprising ideas challenge the reader’s worldview. It is the writer’s equivalent of a laugh. It’s the metric we use to determine if our writing is engaging. It comforts the confused and confuses the comforted. Ideas that are novel but not surprising are the definition of trivia (which sounds a lot like trivial for a reason).
The way you frame your essay to your editor will completely affect the kind of feedback you get. As you get experience sharing your work, you’ll get better at shaping these conversations.
Expression is Compression
In school, the longer we work on an essay, the longer it gets. We’re trained to write bloated thesis papers to satisfy the teacher’s word counts (and if you’re anything like me, you also increased the spacing between every line so you didn’t have to write as much). But online writing is the opposite. Fluff is punished and compression is rewarded.
Moving through the Content Triangle generates new ideas and sharpens your existing ones.
Early ideas become final drafts in the same way that tree sap becomes maple syrup. What begins as a bunch of raw material gets distilled into sweetness. Just as it takes 50 gallons of sap to make one gallon of maple syrup, writing is always a process of distillation. Good writers distill hours (or weeks) of experience into a short, compressed artifact.
Conversations guide the compression process. They help you arrive at battle-tested ideas that’ll resonate and stand the test of time.
Write in Public
THE FEAR OF PUTTING YOURSELF OUT THERE
You’ve spent years thinking about a topic, jotted down a bunch of notes, devoted multiple weekends to research, blocked off your calendar for dedicated editing time, and given every word its due. When there are no more changes to make, the time to publish comes. You start squirming. A rush of doubt overwhelms you. Then, horrors of insecurity. But someway, somehow, somewhere, you find the courage to hit publish.
You aren’t sure what to expect. Deep down, you want a round of applause. Actually, that’s not realistic. Maybe just eight likes. Or at least a few kind replies. How about one text? But you get nothing.
Nothing but crickets of indifference — and it feels terrible because you feel so invisible. This section is about overcoming that feeling of being invisible. Publishing is the cost of admission, but there are time-tested methods to spread your ideas and grow your audience.
A NEW WAY TO THINK ABOUT MARKETING
Effective promotion has worked long before the Internet. Christianity invented viral, word-of-mouth marketing long before engineers in Palo Alto ever did. The 12 disciples were the original brand evangelists (but back then, you didn’t get free brand T-shirts for converting your friends).
The means may have evolved, but the core methods are similar. More recently, Arnold Schwarzenegger became the world’s biggest movie star because unlike the other actors of his time, he saw acting as only part of his job. As he writes in his biography: “Too many actors, writers, and artists think that marketing is beneath them. But no matter what you do in life, selling is part of it.”
His work was only halfway done once the filming for a movie was over. No matter how good it was, it wouldn’t spread without great marketing. Arnold looked down upon other actors who relied on agents and managers to do the marketing for them. By outsourcing promotion, they didn’t just lose a cut of the cash they deserved. They also lost control over how the movie was framed and the narrative of their own career. Little surprise that today, Arnold writes the best email newsletter of any celebrity I know.
AUDIENCE VS. ATTENTION
No matter how good your work is, building an audience will take time.
It’s a slow process, but don’t let that fact turn you off. That’s what makes having an audience so powerful. An audience is valuable because it takes time to build. If it happened quickly, it wouldn’t be a sustainable advantage. You can buy attention, but you can’t buy trust. It has to be earned, and that’s what makes it so precious.
Just because you have attention, doesn’t mean you have an audience. An audience isn’t the number of people who know your name. It’s the number of people you can contact at any time (which is why traditional celebrities don’t have audiences even though they’re famous). Some audiences are far better than others too. Large followings don’t necessarily lead to loyalty, like the Instagram bikini model with 2 million followers who couldn’t sell 36 T-Shirts. And then there are writers like Byrne Hobart whose work is read by some of the world’s smartest people, and Jack Butcher who earns freakish amounts of cash per subscriber.
How do you build an audience?
The Public to Private Bridge
Building an audience begins with attracting people on public platforms like Twitter and Reddit, both of which act like public squares where you can reach people at scale, for free. These public platforms are governed by algorithms that match people with similar interests. Since the biggest ones have hundreds of millions of people, they are divided into tiny subcultures, most of which are too niche to function in the physical world.
Even if public platforms are the top of your marketing funnel, they come with a tradeoff. What they give you in free reach, they take away in the lack of a connection to your audience. Their terms and conditions agreements state that they have a right to kick you off the platform. Since they own your data, you can’t download your follower graph and transport it to another network.
I like Naval Ravikant’s line on this: “Building an audience on a public platform is like building a castle out of sand.” One second, you have a fancy following to show your friends. Next, you’ve been booted off your favorite platform with nothing to show for all your hard work.
Don’t let a public platform control your audience relationships. If the president of the United States can get kicked off Twitter, so can you.
Find people on public platforms. Build a relationship with them on private ones.
Do what James Clear did. He grew his audience on the back of Google, Instagram, and Twitter. Though search engines and social media platforms are fickle, Clear converted ~2 million readers into email subscribers who he can now contact directly at any time. Unlike Twitter and Instagram, Clear’s email list isn’t mediated by an algorithm. He can save and download all the emails he’s gathered at any time. He built his audience by initially standing on the shoulders of a public platform and transferring those relationships to a private one.
I call this process of transferring people from public platforms to private ones “The Public to Private Bridge.”
In the next section, I’ll walk through the mechanics of audience building. First, I’ll show you how to add value on a public platform so readers can find you. Then, I’ll show you how to engage those readers with your website and email newsletter.
7. Engage the Public
FIND YOUR PUBLIC PLATFORM
You can’t launch a random, no-name blog and expect people to magically find it. Start by identifying the places on the Internet where your readers like to hang out. You can go in two directions:
- Big Social Networks: Places like Twitter and Reddit where millions of people can learn about an industry or subscribe to specific sub-communities. Think of these like massive public squares.
- Small Forums: If massive networks aren’t for you, look for intimate public spaces where like-minded people gather. Maybe it’s an industry-specific forum. Maybe it’s a Slack channel focused around a specific theme. Though small forums are less likely to give you scale and reach, they’re a good way to find people who share your interests.
Resist the temptation to build an audience on multiple platforms at once. I once had a conversation with an aspiring online writer. We’ll call him Mike. He’d been writing online for five years, but struggled to build a meaningful audience. When I asked him about his distribution strategy, he told me he’s re-purposing his content for all the major social media platforms: Twitter, Facebook, Reddit, Instagram, YouTube, Snapchat, and even the new up-and-coming ones that everybody knows won’t live up to the hype. All that work paralyzed him. He was so scattered that he didn’t allow himself to commit to a single platform. From Mike, I learned that even if it’s okay to experiment with different platforms in the early days, you should quickly go all-in on one of them.
The Internet is a game of power laws. One of the biggest myths in marketing is that you need multiple marketing channels to succeed. Every creator I know has one public platform that works way better for them than the others… combined. Don’t move to a second platform until you’ve mastered the first.
ADD VALUE TO PLATFORMS DIRECTLY
Reaching people on public platforms starts with adapting your ideas to the network you’re using. Don’t send people to another platform. Reach them where they already are instead. Each one has a different culture. Twitter is focused on ideas, IndieHackers is focused on mid-length forum posts, and Medium is focused on long-form essays. Like any club, participants reward those who make the platform a better place. They intuitively reward good actors and publish the bad ones — fraudsters, hucksters, and link spammers.
As Harry Dry, the founder of Marketing Examples wrote: “The best self-promoters aren’t self-promoters. They take the time to become a genuine member of each community. Share others’ content. Write detailed comments. Make friends.”
My writing coach Ellen Fishbein built her career with thoughtful discussion prompts on the Farnam Street learning community. At the time, the forum had less than 1,000 people, but they were exactly the kinds of people she wanted to meet. Eventually, her posts came to define the culture of the forum. Collectively, her posts received thousands of replies and she became “niche famous” on the forum. A fan of Ellen’s, who found her on the forum, introduced me to her and we’ve been working together ever since.
If there’s anything I’ve learned by writing online it’s that small tweaks in how information is packaged can alter the reach of an idea by orders of magnitude.
On Twitter, write threads instead of linking to articles.
Consider the difference in strategies between two Ukrainian newspapers: The Kyiv Post and The Kyiv Independent. Every public platform wants to keep people on it because they can’t show people ads once they leave. Thus, the algorithm downranks posts that take people off-platform. Though both newspapers were covering the same war, The Kyiv Independent was much more successful because they condensed stories into multi-part Twitter threads instead of sharing article links. Twitter threads led to engagement, engagement led to virality, and virality led to The Kyiv Independent’s rapid follower growth.
As Harry at Marketing Examples wrote:
At the start of the war, The Kyiv Post had 10x more followers
than the Kyiv Independent. Today they have 5x less.” (Source)
DIRECT PEOPLE TO YOUR DIGITAL REAL ESTATE
A bunch of people may know your name, but that doesn’t mean you have an audience. Make it easy for people to engage with your work more deeply.
Link people to your newsletter or an article that expands on what you’ve written. On Twitter, people will link to their website in their bio and their newsletter at the end of a thread (I’ve picked up at least 30,000 email subscribers by writing threads and linking to my email list in the last tweet). No matter where you’re posting, a good bio should tell people what you write about, who you serve, and link to your website or newsletter.
8. Build Your Online Home
As newsletter platforms like Substack have become more popular, online writers are wondering “Do you need a website anymore?”
Setting up a Substack is like 100 times faster than building a comprehensive website. When you’re getting started, Substack is a worthy choice, and in certain cases, a Substack may be all you ever need. But that doesn’t mean personal websites are dead.
Newsletter platforms shine with simplicity, but fall short on their personal touch. The lack of customization features makes it hard to show off your personality. Substack isn’t built for people who want to dial in their aesthetic, sell products, or hyper-customize their site. Instead, it’s engineered for people who want to monetize their writing directly, via subscriptions, and it does that very well.
On Substack, you’re a template in a network of sameness— and that’s where a personal website comes in.
WHAT’S UNIQUE ABOUT A WEBSITE?
The difference between Substack and a website is like the difference between a mall kiosk and a retail store. Sure, you can sell clothes from a kiosk. You have low overhead and a bunch of walk-by foot traffic too. The problem with a kiosk is that each one looks undifferentiated to the casual observer. In a retail store, you can control the branding, lighting, sound, smell, the checkout experience, and the whole shebang.
Like a retail store, personal websites require up-front investment. But you can do whatever you want to make it yours. Your online home is an all-in-one bundle — a resume, business card, store, portfolio, and whatever else you please. The best ones are expressive, and therefore, memorable. A testament to who you are and what you stand for.
There are two key benefits of a website that you don’t get through newsletter platforms:
- Navigation: The ability to guide your readers to work that resonates with them.
- Aesthetics: The ability to express your personality through visuals.
Newsletter platforms don’t guide readers towards the ideas they care about. They have a recency bias, and care more about email delivery than a coherent archive of your work. Since the archive is sorted chronologically, it prioritizes things that we published recently, and so the best stuff is often buried. If you’re writing timeless, “evergreen” articles, you seriously want to consider a website.
Websites let you design your reader experience. By using a Start Here page and Essay categories, you let readers choose their own adventure. Guided by their curiosity, they carve a unique path through your body of work.
YOUR ‘START HERE’ PAGE
Your Start Here page will be the first thing people see when they land on your site. Readers want direction. They want to know who you are, what you write about, and which essays they should read first. Aim to achieve all that in 10 seconds or less.
Here’s a list of things you can share on your Start Here page. Pick a few, but not all of them:
- Photos of yourself
- Short introduction
- Quick bio
- List of interests
- Where you’ve worked
- What you’re working on
- Featured essays
- Book recommendations
- Links to podcasts you’ve been on
- Your life story in 50 words or less
Don’t just share a hodgepodge of details though. Aim for a higher-level narrative. For example, everything on Ana Lorena Fabrega’s Start Here page revolves around childhood education.
She talks about what she does for work and her crusade to rethink education. When she writes about herself, she gets specific. Instead of saying, “I have a lot of experience in schools,” she writes: “When it comes to schools, I’ve been around the block a few times. Growing up, I attended 10 schools in seven different countries. I then became a teacher and taught hundreds of kids in New York, Boston, and Panama.”
Then, she links to articles, podcasts, and YouTube videos that show how she thinks.
Most essay pages are terribly organized. Instead of featuring the writer’s best pieces, they overwhelm the reader with a bunch of essays listed in chronological order. New readers shouldn’t necessarily start with the piece you just published. For example, this guide is way, way, way too long to recommend to a reader who just landed on my site and has no idea who I am.
I like the way Julian Shapiro displays his essays. He uses an information hierarchy to guide people to his thinking about startups, writing, and exercise. Through design, he’s letting the reader choose where they want to start. And if they feel like starting with something shorter, they can click on the “short blog posts” section instead.
There are all sorts of ways you can categorize your published ideas: by topic, by length, by format, or by date. Consider how tags can help your reader experience. Not only do they create groups on your Essay page, but they let you feature ‘Recommended Articles’ at the bottom of each essay.
Newsletter platforms restrict the aesthetic quality of your site. You typically get to pick one accent color, and then you choose from one of three fonts (modern, newspaper, or robot world). Everything looks the same.
But when somebody lands on your site, they should be able to get an instant feel for you. Through design, you can instantly communicate what would otherwise take 1,000 words.
Tim Urban, who writes a blog called Wait But Why, does design as well as any online writer. The second you open his site, you realize something’s different about it. Instead of being buttoned-up, the site looks like it was designed by a 4th grader because of all the little stick figure drawings; and instead of professional photos, he uses hand-scribbled drawings. But since his essays are so well-researched, the juxtaposition between playfulness and intelligence is hilarious. His aesthetic, combined with his voice is so distinct that he can basically write about whatever he wants, and it’ll still feel like a “Wait But Why” post.
That unique look can help your Start Here page too.
Charlie Bleecker is a pseudonymous writer who pushes the limits of openness and vulnerability. Compared to Ana, her Start Here page feels less like a classroom and more like a campfire (to match her writing style). Sometimes she’s snarky, sometimes she’s crazy, sometimes she’s unhinged. But no matter the topic, she writes with honesty — like this story about the one time she accidentally tripped on mushrooms.
She’s not hiding… there’s literally a swear word at the top of her Start Here page. With it, she went all-in on who she is, which is why it combines the enchantment of Harry Potter with the mystery of a Gillian Flynn thriller. Aesthetically, from the way her name is displayed to the high-contrast image of her, her Start Here page is as spunky as her writing.
The visuals set the tone, and bring you into the right headspace before you start reading.
Start with a site that is simple, but distinct. Eventually, as you build a writing habit and grow your audience, it’ll grow into a full expression of yourself. As you build it, don’t forget what matters most: writing and publishing.
Don’t forget, your website isn’t just a place to share ideas or express yourself. It’s a place to grow your audience too, and the best way to do that is by capturing email addresses. You can include email captures at the top of your Start Here page, in your footer, or nested in your essays.
At first, you can use the stock “Subscribe” button, but as your site matures, you want to be specific to your potential reader on why they should subscribe. Be specific, be persuasive, and offer something. This gives them a solid reason to cross the Public to Private Bridge.
9. Start an Email Newsletter
Getting people to your website isn’t enough. The goal is to get them on your email list. If you’re posting on public platforms without driving people to your private ones, you’re leaving cash and friendships on the table. Online relationships (like real-world relationships) are best built through repeated interactions. If someone isn’t on your email list, they either have to seek you out directly, or hope to come across you when the algorithm feels like it.
No matter what kind of writing you want to do, waiting to build an email list is one of the biggest mistakes you can make.
As every experienced marketer will tell you, email subscribers are digital gold. I’m embarrassed to admit that I was a card-carrying member of the “email is going to die” club. Fortunately, I’m no longer part of that cult. Now that the head on my shoulders is better adjusted, I know email is going to stick around because of how entrenched it is in professional circles.
Social media is magnetic, but email is sticky.
On Twitter, even though I have more than 300,000 followers, only my most viral tweets reach that many people. Meanwhile, the emails I send reach basically every person who subscribes to my newsletter (partially because everybody checks their inbox). Just as subscriptions lead to recurring revenue for software businesses, email lists lead to recurring attention for online writers.
Send enough quality emails and you won’t just have an email list — you’ll have a group of people who trust you and have chosen to hear from you consistently and indefinitely. That’s why my email list is my most valuable professional asset. In the four years since I started Monday Musings, I’ve never skipped a single edition. It’s expanded the number of people I can keep in touch with by an order of magnitude. The same thing can happen to you. With an hour of work per week, you can keep a relationship active with thousands of people who want to learn from you and hear about what you’re working on. In the five years since I started Monday Musings, I’ve sent an edition every single week.
Writing online without building an email list is like playing Monopoly, passing GO, and not collecting $200.
There are two ways to think of newsletters. Some people see newsletters and articles as separate (like me). They see newsletters as a short hello and save more substantial thoughts for articles on their website. Others see newsletters and articles as the same thing. I have one newsletter for each strategy (don’t copy me. If I wasn’t a full-time writer, I’d use a simpler strategy). Monday Musings features mini-essays, while Friday Finds is more like a digital postcard with my favorite links from the week.
In this section I’ll cover both strategies, which are equally useful.
When Articles and Newsletters are Different
Separating articles from newsletters is the more traditional route. Here, the biggest mistake you can make is to spend so much time on your weekly newsletter that you forget to write articles that’ll live on in perpetuity.
Think of newsletters like little “Digital Postcards.” They can be quick and personal. They’re less about cramming your best ideas and prose into an email, and more about staying in touch. It makes sense given the fleeting nature of email. Rather than putting essays in your email, you can link back to your personal website.
Caption: If you need an example of what a friendly ‘Digital Postcard’ looks like, here’s one from Justin Mares, the founder of Kettle & Fire.
If you can’t commit to a regular newsletter, send a quarterly newsletter to friends and family. Pick 2-3 items from the following menu: talk about what you’ve been working on, an eye-opening story, something you learned about your Personal Monopoly, a few of your favorite links, or a photo with a short description of what’s going on in it. Keep it light and fun, but still intelligent. Everybody enjoys receiving their friends’ personal updates.
Get in the habit of sharing your newsletters to other platforms. I shared my first personal update on Facebook and Linkedin, which attracted a swarm of friends and family.
When Essays and Newsletters Are the Same
Substack pioneered this format. When you write on Substack, each article you publish is automatically sent to subscribers as a newsletter, which makes it the simpler option.
Using Substack as a de facto online home has worked for many creators like Packy McCormick, a Write of Passage alum. He built a giant audience with more than 100,000 newsletter subscribers by publishing straight to Substack. It’s easier to publish there because you don’t have to worry about designing your site, paying for a subscription, or linking an email capture form to your site. Substack is free and the emails you collect are yours to download too. The tradeoff is that every Substack article basically looks the same. You can’t change your font and the archive section is pretty clunky.
From Packy, I learned that if you’re going to use Substack to build a Personal Monopoly, I recommend using a bunch of branded images. For Packy, they came in the form of pop culture memes. Building a Personal Monopoly comes easier when you have a distinct visual identity.
Which format should you choose?
Both strategies work well.
If the thought of setting up a website overwhelms you, skip it. Writing consistently is the most important thing. I detest anything that takes you away from that. In the early days, you don’t need the perfect system. You just need to write frequently, so commit to a publishing schedule and stick to it.
Some people ask: “In the age of information overload, shouldn’t you only publish when you have something to say?” When you’re a beginner, no. Once you’ve been writing for a while, do what you want. If, eventually, once writing’s become a habit, you feel compelled to step back and publish only when you’re compelled to do so, go for it. I like the motto: consistency comes before choice.
No matter what option you choose, remember that you need a public platform to spread your ideas and connect you with new readers. Once they find you, it should be easy for them to sign up for your newsletter.
The Craft of Internet Writing
Good marketing can only take you so far. You have to write well too. Like a startup, a company’s marketing budget can number in the millions, but they won’t be a success if the product is terrible and doesn’t solve a worthy problem. Writing is the same. Good products win. Though there’s an element of luck in success, J.K. Rowling is such a talented writer that she’d be successful in any version of the simulation.
School didn’t train me very well though. In school, my teachers focused on grammar, clauses, and tenses — things that don’t cut to the heart of great writing. Worse, I was trained to pen bloated, verbose MLA-cited essays. Since the standard methods of writing instruction didn’t work well for me, I developed my own.
In this section, I’ll show you how POP Writing can make your ideas memorable. Instead of encouraging you to reach preposterous word counts like your 6th grade English teacher, I’ll show you how to organize sprawling ideas into singular concepts with memorables titles. And finally, I’ll show you how to hone your voice so you can stand out as an online writer.
10. Make it POP
Good writing has three components: it’s Personal, Observational, and Playful. Writing that feels stale is almost always lacking in one of these three dimensions.
Every writer has a pillar that comes most naturally to them. Observational writing is easy for me, but only after four years of consistent writing did I start sharing personal stories.
I’ll describe the three pillars of POP Writing below:
Revealing things about yourself helps readers connect with you. Facts aren’t enough. You can find those on Wikipedia. Instead, write about intimate emotions or intense experiences. Tell stories about your life (This one is true: In 4th grade, I played the saxophone at my school talent show. But because I was too weak to hold it, I had to rest it on a chair, which made me so embarrassed that I bombed in front of everybody, and I haven’t once picked up a saxophone since). If your words make you feel naked, you’re probably onto something.
Personal writing goes wrong when it lacks the other components of POP because it’s neither insightful or fun to read. Remember, nobody cares about you as much as you do. If you don’t distill the lessons from your life stories, they aren’t relevant to others.
So many writers have stage fright, especially at the beginning. If you’re scared of judgment, write under a pseudonym.
The idea that our parents, co-workers, or clients could potentially read our essay is enough to give us the heebie-jeebies and scare the life out of our writing voice. Writing under a pseudonym lets you write with honesty. A pen name can give you joy without judgment, and freedom without fear. When you write from behind a cloak, you can say what’s truly on your mind and pluck the hearts of your audience. Don’t think of a pseudonym as a mask to hide behind, but as a key to uncover what’s locked within you. When we step into a costume, we feel comfortable stretching the boundaries of our identity. Every day has the freedom of Halloween.
Susan Sontag once said that “writers are professional observers.” It’s true. Good observational writers either have a deep knowledge set or a distinct way of looking at the world, which makes readers say: “Huh, I’ve never thought of it like that before.”
When writing is only observational, it’s boring. School textbooks come to mind because they are neither personal or playful.
Observation will come easily to you once you start taking notes. With a database of facts and epiphanies to draw from, you’ll be able to expand your readers’ knowledge set.
Jokes, riddles, slang, coined terms, funny phrases, and thought experiments are all part of the repertoire. Sneak your sentences some swigs of tequila until they’re a little tipsy (too much will make your reader gag). If you’re making your
prisoner reader smile, you’re onto something. Like relish on a hot dog, playfulness is a condiment — not the main dish. You don’t need to TRY to make people laugh. Instead, write what makes you smile and you’ll be surprised at how well your words will resonate with others. Smiles are contagious. Pass them on.
How much sizzle you want depends on why you’re writing, what you’re writing about, and who you’re writing for. You probably shouldn’t swear in a corporate memo, but by all means, turn up the playfulness when you write for the best friend group chat. The Economist (which writes for a high-end clientele) doesn’t have the same voice as Barstool (which writes for bar-talking Stoolies), and that’s the way it should be. But if your writing is only playful, it’ll read like a tabloid without substance.
11. Find Your Key Idea
I’ve always liked the movie title: Snakes on a Plane.
It tells the viewer so much about what they’re going to watch, and it adds suspense without spoiling the plot. As a movie-goer, you know you’re not going to get parrots on a train or elephants in the ocean. That simple title also helped the creators because they could instantly discard anything that didn’t point back to the core theme: Snakes on a Plane.
I call this simple idea a Shiny Dime.
A shiny dime is the smallest viable idea you can write about. Like “Snakes on a Plane,” it’s the most compressed distillation of what you’re trying to say. Psychologically, shiny dimes are a coping mechanism for writers who foolishly try to explain their entire worldview in a single article. They’ll talk about every company they’ve ever worked for, every book they’ve ever read, and every experience they’ve ever had until they end up with gargantuan topics like “Everything You Need to Know About Fashion” or “Artificial Intelligence in the Digital Age.”
Good writing is focused. It orbits around a single point. Once you find your shiny dime, you can instantly reject every idea that doesn’t relate to it. Just as every verse in a song should relate back to the chorus, every idea in an essay should relate back to the shiny dime.
You don’t need many ideas to write a successful essay. You just need one. Instead of focusing on a bunch of tangentially related ideas, a shiny dime will push you to double… triple… and quadruple down on the best ones you’ve already found.
A coined phrase is the most compressed version of a shiny dime.
When you distill an essay down into a simple word or phrase, you not only create a memorable title for your work, but you make a contribution to the English language. Think about phrases like “FOMO” (fear of missing out), “doom scrolling,” or “the meat sweats.”
Coined phrases are more than just short and insightful. They’re catchy. They’re earworms. They’re fun to say out loud, and once you hear one, you can’t help but repeat them while talking to friends. When your essays can be compressed down into lingual memes, you open yourself up to free viral marketing.
Coined phrases often hold these characteristics:
- Surprising – They surprise us in the moment, but feel obvious in retrospect. Once we see them, we can’t unsee them.
- Ambiguous – They create suspense and spark the reader’s curiosity.
- Visual – Good metaphors activate the reader’s senses and are as vivid as they are true.
- Fun – Like a jingle, you can’t help but say them out-loud.
12. Develop your Voice
Your voice is about how you write, not what you write. It’s your personality on the page. A unique voice gives you flexibility and freedom. Writers who are known for covering a topic have to stay inside that box. But if you have a unique voice, die-hards will follow you wherever you go. Hunter S. Thompson comes to mind. His voice was as unique as a fingerprint, which is why he was able to cover such a breadth of topics like horse racing, political campaigns, or a motocross race in Las Vegas.
Great writers have singular and instantly identifiable voices, which is why you can read a paragraph-long excerpt of David Foster Wallace and immediately know it’s him. His language is so descriptive that he can say more in a paragraph than you can in a year. Like the Space Mountain roller coaster, you’ll feel completely in the dark as you read his work, but have teary eyes by the time you get off the ride. You’ll shake your head like a dog shakes their body when they get out of the water, and say: “Woah, that was a hoot.”
If you have a distinct voice, you don’t need to have all the answers because readers will enjoy going on the journey with you so much. They’ll want to crawl inside your mind and see the world from your perspective for a little while. The more distinct your voice, the wilder the ride will be.
Great artists are distinct. In the world of art, I think of Van Gogh’s swirling lines; in the world of design, I think of Kelly Wearstler’s flamboyance; in the world of photography, I think of Ansel Adams’ black-and-white landscapes; in the world of acting, I think of Matthew McConaughey’s sayings like “Alright, Alright, Alright.”
Good writers have distinct voices too. From talking to writers, I’ve found that singular voices are developed by looking in uncommon places. Some say that Shelby Foote was respected for his Civil War expertise, but beloved for his storytelling. Though he was a historian, he credits Marcel Proust’s novel, In Search of Lost Time as a key inspiration. It’s 3,000 pages and he’s read it nine times. Even though Proust’s ideas have nothing to do with his area of study (The Civil War), his fingerprints are all over his writing — which is why the details are so vivid. Likewise, the legendary biographer Robert Caro says: “If you want it to endure, the level of the writing has to be the same as great fiction.”
Like Foote and Caro, take inspiration from people who are nothing like you. A unique voice can show up in all kinds of ways. Packy McCormick injected humor to the antiseptic world of business writing, and explained ideas with memes. Tim Urban got tired of buttoned-up explanations of intellectual concepts and played around with stick figure drawings instead. Nassim Taleb personifies his ideas by pulling from a cadre of make-believe characters like Fat Tony, an Italian guy with serious street smarts who belongs in a mafia movie like The Godfather.
Like your personality, your voice will take time to develop. There’s no substitute for writing (and publishing) frequently. If you don’t feel like you’ve found your voice, write more.
You ain’t gonna think your way to finding your voice. Don’t get upset with your lack of progress until you’ve published at least 50 articles. As you write, experiment with different styles like a teenager going through phases. One day, they’re wearing Hot Topic. Next, they’re a jock. And next, they’re throwing it back to the 70s and dressing like Danny and Sandy from Grease. Like an angsty teenager, good writers are always experimenting with new styles.
Every person has a distinct voice. As Tyler Cowen put it so eloquently: “It’s the weird that’s truly normal. It’s how people actually are—what they really care about. In a sense, you’re getting them out of the weird. The weird is the stage presence we put on—all the ‘puffery’ and unwillingness to say what you really think.”
To Cowen’s point, I’ve yet to meet somebody who isn’t exceptionally strange once I’ve gotten to know them. The problem is that so many writers get stuck with Writer Brain and Memo Speak. Sure, some people are weirder than others, but everybody has parts of them that are one-of-a-kind. The difference between somebody who writes with the personality of a doorknob and somebody whose prose you can instantly recognize is the decision to embrace and enhance your quirks instead of running away from them.
IMITATE, THEN INNOVATE
I’ve heard people say: “Voice is just something you have. Don’t think about it. It’s natural. It just comes out, so don’t clutter your mind with outside influences.” While this might eventually be true, it’s hard to write authentically in the early days. The ideas are beautiful in our head, but awkward on the page.
To uncover your voice, study and imitate your favorite writers. Admiration (and its twin named Envy) is an internal compass that tells you who you want to become. We’re inspired by writers when we see a piece of ourselves in their work. The goal of imitation isn’t to plagiarize (or even to copy them word-for-word). The goal is to understand how they express their personality through language.
Early in his career, the artist Cézanne received a letter from the novelist Émile Zola, who shared advice for improving his craft. Paris was the best place to study painting because it offered so many avenues for imitation. Zola told him to start the day by visiting museums like the Louvre to copy the work of old masters. In the evening, he returned home to paint his own work. The next day, repeat.
The craft of writing may be different, but the method is the same.
Reverse engineering your favorite writers starts with changing how you read. Don’t just highlight their best ideas. Highlight the ways they use language too. Notice their word choices and sentence structures. Notice the analogies they use and how they transition between paragraphs too. Try on different writing styles and see how they feel. Most of what you try will feel unnatural, but some of it will feel right, and when it does, double down.
Through reading and experimentation, you’ll come to sound more like yourself. Beethoven imitated Haydn. Picasso imitated Cezanne. Johnny Carson imitated Jack Benny. Beethoven, Picasso, and Carson may have started as imitators, but we talk about them because they eventually found their own fingerprint of a style.
Their stories show us that deliberate imitation can reveal what makes us unique. One Hollywood actress told me she has to rehearse some lines 100s of times before she can “be natural” on camera. All those anecdotes remind me of a line from Miles Davis, a jazz musician who once said: “It took me years to play like myself.”
DEVELOPING YOUR STYLE
Though you should follow the rules early on, you’ll eventually want to break away from them to develop your own style. The problem is that so much contemporary writing lacks edge. It all reads the same. Just as logos are homogenized and Instagram pushes girls to look like Kim Kardashian, it seems like every non-fiction book follows the same regurgitated formula of making an assertion and backing it up with a study — over and over again, until the reader falls asleep.
When did we decide we needed a scientific study to justify every obvious intuition? Where’s the spunk? Where are the flames of intoxicating passion? And where are the Hunter S. Thompson’s of the world who write with such fiery prose that each sentence and each paragraph is unequivocally theirs?
Contemporary non-fiction also follows the same treated blueprint of short sentences, simple words, and logic so basic a five-year-old can understand. And yeah, it’s efficient, but we’d all benefit from some more unhinged writers who look at what you’re “supposed to do” and instead of bowing down, give it the New York Salute.
In the pursuit of excellence, painters like Claude Monet are a good model to follow. Though his Impressionist style eventually shattered the conventions of art, his early paintings demonstrate technical mastery. When he broke the rules of painting late in his career, he did so intentionally, and that intentionality was enhanced by a mastery of standard techniques.
Look at the paintings below and you’ll see that the famous water lilies he painted late in his life had none of the realism he displayed early in his career. Using a more abstract approach, he shattered the rules of landscape art. Unlike other paintings of the time, his water lily paintings have no sky, no horizon, and barely any stable reference points.
The writing equivalent is that perfect grammar & syntax is a good place to start, but not necessarily the best place to end up. If you doubt this, try reading a piece from somebody who doesn’t know proper grammar. It’ll hurt your brain.
Ideas and personality are what ultimately matter though. Nobody has ever recommended a book because there weren’t any typos.
You can do things your own way. I promise: the rules of composition weren’t handed down to Moses on stone tablets — which is why we devour Reddit comments written by neckbeards in their underwear, but get bored with academic writing by the second paragraph.
Don’t get too carried away with style though. It’s like basketball. Master the basics first. Stephen Curry can make behind-the-back passes whenever he wants, but my 4th grade basketball coach was right to immediately take anybody who tried such a superfluous maneuver out of the game.
Keep your grammar simple at first. Extravagant punctuation can distract from your main message. If you break the rules, do it deliberately (like Monet).
Be careful with tools designed to improve your writing, especially once you have some experience. Turn off the recommendations in Google Docs. Don’t use Grammarly while you write because it’ll make your writing sterile. But if you’re like me and make tons of typos, go ahead and use it to check what you’ve already written.
I like Michael Mayer’s line about writing software: “Writing tools often lower variance which is good if you’re a bad writer and bad if you’re a good writer.”
The better your writing, the less you should rely on software tools. Like life itself, you should generally follow the rules. But if you follow all of them, you won’t end up anywhere interesting. And since grammar suggestions are the bureaucrats of the writing world, “accepting every suggestion” is a recipe for tin-eared sentences.
Ultimately, you should aim to develop a distinct and unmistakable voice, which will become a pillar of your Personal Monopoly.
Conclusion: Personal Monopoly
I used to fear writing about a single subject because of the way it would narrow my horizons. In retrospect, I didn’t appreciate the benefits of such commitment.
Write frequently around a consistent theme. If you do, you’ll attract inbound messages you could never imagine. Some people will want to work with you. Others will become your closest friends. Others will open doors you didn’t even know existed (like the time the former CEO of Home Depot funded five-figures worth of grants for my writing students). If you write on the Internet and become known for something unique, the same things can happen to you.
Writing well and consistently makes you top of mind for people in Internet communities. Serendipity will come next. The number of opportunities that come your way will astonish you and everybody close to you. As my girlfriend often says to me: “The amount of crazy coincidences in your life is like something out of a fantasy novel.”
Strangers will find you on Google or the social media app du jour. Friends will think of you when they need help. Your published writing will double as a proof of work mechanism for how much you’ve thought about a subject. For decades, books have been the world’s best business card because they instantly signal rigorous thinking. Now, online blogs are having a similar effect. You don’t need to spend three years writing a 300 page book to become known for a subject. Instead, you can write 500 words once a week, and distribute them instantly and directly to your audience.
What is a Personal Monopoly?
A Personal Monopoly is a unique combination of skills, interests, and personality traits. The more unusual it is, the more valuable it’ll be because there are so few substitutes. A distinct Personal Monopoly makes people say: “Wow, I’ve never met anybody like you before.”
On the Internet, where everybody is screaming for attention, only the most differentiated people stand out. I’ve always liked Derek Thompson’s idea that “The Internet is Tokyo.” The Japanese capital is famous for its weird shops (such as a museum of kites, a feudal Japan-themed restaurant where the waiters are dressed as ninjas, and a place where you can take a real-life Mario Kart tour of the city). These niches can only exist because the city has a population of 40 million people. The Internet is like Tokyo on steroids. People can be niche at scale.
Asking the question of “What is my Personal Monopoly?” often leads to a low-grade identity crisis. Who am I? What do I stand for? What do people want from me? Should I write about the liberal arts, science funding, or the economics of Babushka dolls?
Well, let me help. Every successful Personal Monopoly has basically four characteristics:
- Complimentary: Different skills come together to form a special superpower. Since the elements work together, the sum of a Personal Monopoly is greater than its parts.
- Useful: People demand the Personal Monopoly because it provides something rare and valuable.
- Specific: By precisely defining your Personal Monopoly, you instantly stand out and distinguish yourself.
- Experiential: The more your expertise is rooted in experience, the harder it is to replicate. Or, to state the inverse, the easier it is to learn something on the Internet, the less valuable that knowledge will be.
A Personal Monopoly can take on many different forms. Some, like Lenny Rachitsky, have niche expertise (which makes him a one-stop shop for all things startup growth). Others, like Tim Urban, pair an unforgettable writing voice with intellectual rigor. Readers come back for an experience.
For some writers, their Personal Monopoly path is clear. They know exactly what they want to write about and how they want to write about it. Like an architect, they can design the blueprints in advance and follow them as planned. Little variations are okay, but certainly nothing major.
Finding a Personal Monopoly isn’t so easy for most people though. Some don’t know what they want to write about. Others haven’t found their voice. And then there’s a stubborn few who refuse to commit to anything consistent.
If you’re uncertain about your Personal Monopoly, I say: just keep writing.
Don’t let a lack of clarity stop you. You don’t have to know your Personal Monopoly before you start. Don’t worry about “confusing your audience” or anything like that. Putting your ideas on paper and publishing consistently will show you what you actually care about. Once you’ve published a litany of articles and heard back from readers about what they enjoyed, your Personal Monopoly will emerge.
To find it, you can follow the three pillars of writing, which we’ve discussed in this guide:
- Write from Abundance: Curate your online feeds so you can pull from a unique set of ideas and information.
- Write from Conversation: Get feedback from your friends and readers to learn which topics and quirks you should double down on.
- Write in Public: Write consistently. Develop your command for language, so your real-life voice and expertise translates onto the page. Once you’ve published a bunch of articles, look back on what you’ve written to identify the patterns in your thinking.
DOWNLOAD YOUR PERSONAL MONOPOLY GUIDE
Become known as the best thinker on a topic and open yourself to the serendipity that makes writing online so special. Uncover your strengths, clearly communicate your values, and start building your reputation online. Download the guide to your Personal Monopoly.
Where to Begin?
There are many ways to write. Your system can (and probably should) look different from mine, so think of this guide as a starting point, not a manual you have to copy. Throughout it, I’ve tried to keep the advice broad enough to be widely applicable, but specific enough to be practical.
Your next step depends on where you are as a writer.
If you’re a beginner, starting out:
- Build Your Systems: Integrate the three pillars of writing into your lifestyle. Writing from abundance will shake you away from writer’s block, writing from conversation will get your ideas flowing, and writing in public will attract the kind of inbound that makes online writing so magical. Don’t get tangled in the more complicated stuff until you’ve integrated these three pillars. No custom websites, expensive growth hacks, or NASA-grade note-taking systems. Don’t worry about your Personal Monopoly either. It’ll come if you write consistently.
- Develop a Writing Routine: Set up your note-taking system, start capturing your best ideas, and turn them into essays. Pick a publishing cadence and stick to it. If possible, aim to publish one article per week. To do that, you’ll either want to write every day for 30-60 minutes or, free up one day per week to write an article from start to finish. Become obsessed. If you do, your chances of success will be much, much higher. Give your mind time to wander as well. A busy schedule will suffocate your spirit, but free time is nuclear fusion for creativity.
- Live Like a Writer: If your ideas are boring, get a life. If you already have a life and your ideas are still boring, you’re not listening carefully enough. If you don’t listen to yourself, you’ll suppress your most honest and fire-branded ideas; if you don’t listen to others, you’ll be deaf to the wisdom of experience; and if you don’t listen to the world, you won’t see how the wick of opportunity surrounds you, waiting to be kindled by an adventurous spirit.
- See the World Differently: Writing consistently makes you see the world through a new lens. Every experience, epiphany, and conversation becomes potential inspiration for your craft. Take notes. Pay attention. Writing isn’t some intellectual pursuit separate from your life. Writing is the translation of your life into words that outlive you.
As you develop your writing process, mix and match different techniques. Don’t try to implement everything at once. Focus on what resonates, and discard the rest. Don’t confuse the process for the end result by obsessing so much over the tactics in this guide that you forget about what’s actually important: writing and publishing.
If you’re an intermediate writer with a small body of work:
- Stay consistent so you can sharpen your craft: Set deadlines in order to publish consistently. This intermediate phase can last years, even for the best. James Clear honed his craft by publishing two articles per week for four years. Morgan Housel published more than 1,000 articles. You’re going to be writing a lot, so find ways to relish the process. Pursue a combination of careful reading, deep conversations, an intellectual friend group, purposeful travel, and quiet time for contemplation.
- Build your audience: Promote your work. When you publish a piece, share a summary in a Twitter thread or a popular Internet forum like Hacker News. Link to the article on your website. If they like it, they should be able to easily subscribe to your email list. Go on podcasts. Collaborate with other writers, so you can cross-promote each other.
- Move towards a Personal Monopoly: Publishing dozens of essays will teach you something. Maybe you hated that topic you thought you loved. Maybe something went viral and it surprised you. Maybe readers love the risks you took with your writing voice, and now, they’re encouraging you to double down on them. Whether you want to perfect your website or double down on what you write about, walk in the direction of your Personal Monopoly.
If you’re an advanced writer with a bunch of published articles and a massive audience:
- Call Me: I want to learn from you.
- Monetize your writing: Turn your writing into cash. Start a company, grow your existing one, launch a subscription newsletter, apply for a grant, or switch to a better job. That monetization will fuel your writing endeavors because you’ll be able to devote so much more attention to it. The things people are willing to pay you for can inform your Personal Monopoly.
- Solidify your Personal Monopoly: Make a commitment. Explore the nooks and crannies of an idea. Invest in a website, so you can become the one-stop shop for whatever it is that you do. Expertise isn’t something bestowed upon you by the gods of credentialism. It’s something you cultivate with deep thought, careful research, and a serious writing practice. Ultimately, you cannot copy anybody else’s Personal Monopoly. You have to find your own. If you do, online writing will come easily to you and the gravitational pull of your ideas (and personality) will bend the Internet to your innate interests.
The world has changed. Writing in public is no longer reserved for a special class of people like journalists and professional authors. But today, anybody can do it.
When you write online, you unleash the full potential of the Internet. You’ll open doors to meaningful work, vibrant friendships, and a life of freedom and adventure. Your ideas work for you while you sleep — 24/7, all around the world.
But I get it. Writing is hard, especially when you do it in public. You’re birthing something into existence, so of course it’s painful. (Writing this guide was like birthing a whale.)
To write something, you have to do things, collect ideas, process them, put words on the page, structure them, edit them, rewrite them, and publish them to your site — and that’s all for one article. Then, there’s the emotional challenges: writer’s block, imposter syndrome, lack of time, judgment from strangers, and criticism from friends.
If you want to dive deeper into the system I’ve shared in this guide, join me in Write of Passage. While you could embark on this journey alone, it’s better to do it with friends. A community of trusted writers will give you the feedback you need to learn, the support you need to grow, and the courage you need to take risks.
Your future is waiting to be written. Your story is waiting to be told. Your knowledge is waiting to be shared. You’re meant for more than superficial friendships and endless Zoom calls for a job you can’t stand. The Internet could become your most powerful asset, if only you were using it correctly. Now that you’ve finished this guide, you have the tools to do that.
The next step is to actually write.
Writing an essay like this isn’t a solo endeavor (writing from conversation).
Thanks to my co-founder, Will Mannon for the hundreds of hours he’s devoted to critiquing and improving these ideas over the past three years. Also, thanks to Michael Dean for the laborious rounds of feedback he provided. Seriously, he put God-mode levels of effort into this piece. I’ve been writing online for seven years, and I wouldn’t have been able to see these concepts with fresh eyes without him. I hope you find an editor who cares as much about the craft of writing as Michael.