The Ultimate Guide to Writing Online

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 talk about 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 from Tyler Cowen’s Emergent Ventures program 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 to 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.

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 to 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 up 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.

No exceptions.

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.1

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, in conversations, and in the ordinary moments of my life. All those notes became intellectual fodder for future pieces.

AMBIENT RESEARCH

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.2 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.3

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.