What I've Learned About The Art AND Business Of Online Writing After 3 Years Of Writing Everyday

What I've Learned About The Art AND Business Of Online Writing After 3 Years Of Writing Everyday
Photo by Glenn Carstens-Peters / Unsplash

Great writing makes mundane things feel magical, and magical things seem simple.

I experienced this the first time I read Flow: The Psychology Of Optimal Experience by Mihaly Csikszentmihalyi in my first semester of Freshman year at College. I was lonely after losing my first 14-person friend group. Turns out, late nights spent playing video games, combined with growing up in a small rural town and little social interaction, doesn't develop the social skills needed to form authentic friendships.

Anxious, lost, and confused, I picked up Flow on a whim.

And the world turned upside down...

Csikszentmihalyi introduced me to the concept of flow, the state in which you become fully immersed in the present activity and lose consciousness of the self. Among other factors, it most often occurs when the challenge of an activity meets your respective skill. Flow explained the feelings I had playing video games in high school, the late nights spent reading fiction in my room, and the difficulty I had making socializing an enjoyable activity.

So many things locked into place at once, the world became magical.

I became inspired to embark on an adventure of turning social interaction into the flow activity gaming and reading are for me.

Clearly, great writing can change your life. After that experience, I have become entranced by what makes great writing great. In this article, I will distill my answer to this question from over my three years of writing every day and reading great writers like Nicolas Cole, David Perell, Brandon Sanderson, Matthew Dicks, and Tim Urban. This isn't one of those articles telling you cliche things like less is more, you should write every day, writing is thinking, yada yada yada. You can go read Buzzfead and sacrifice your soul to Satan if that's the kind of lessons you're looking for. No, I'm going to give you the Caviar of writing lessons.

By the end of this article, you'll know the first principles of creating incredible transformative writing like Flow by Csikszentmihalyi and how to identify it when you see it.

So in no particular order let's hop in.

Writing Is Music

Ever read great writing aloud?

It sounds like music. Nicolas Cole’s writing is like a beautiful violin solo—fast, choppy, and stabbing. Brandon Sanderson's writing is like a rising Cello build-up—slow initially but with an explosive climax. Mine is like a clarinet--playful, bubbly, and fast.

Great writing is as pleasant to the ears as it is to the eyes.

That's why I read everything aloud before publishing. How do you make your writing more musical? Mix short with long sentences; if all your sentences are the same length, you'll bore the reader. Mix up your word choice. Alliterate by starting sentences or sequencing words with the same letter. See. Use repetition to hammer home a point. Again. And again. And again.

But whatever you do, don't use a triangle--who plays that instrument anyway?

Writing Is A Team Process, But With Who?

The act of writing itself is a profoundly solo endeavor.

No one else can write the words for you (unless you hire a ghostwriter, but even in that case, you still provide the ideas). But--and this is a big BUT--writing is a collaborative process nonetheless.

As a writer, you're on a team with your favorite authors your readers.

Your favorite authors help you cultivate your writing voice and give you ideas. And your readers give you feedback, especially on if you got your point across. As much as I wish you could zap the exact meaning behind your words into a reader's head, you can't.

Everyone perceives the world differently.

You can think of it like this: words create movies inside your head.

But unlike in film, where the movie is crystal clear, your mental movie is foggy mess influenced by your unique genetics, interests, relationships, and experiences in the world. Your definition of a word--known as a term--might be different from the readers. So great writing can't just be about what makes sense to you.

You have to align your terms with the reader--align your mental movie with theirs.

If your readers' term for notetaking is writing things down to remember for later, and your term is the process of connecting and cultivating ideas to grow knowledge, you can't have a productive conversation. So, you must be explicit with the definitions behind the most integral words of your piece. Literally state your term for critical words and give examples.

It's better to explain too much than too little.

Another aspect of creating a great mental movie is being as specific as possible.

If you're telling a memory of playing tennis in childhood, describe the exact tennis racket. What color were the strings, what was the brand, how did it smell--okay maybe not that last one. Of course, sometimes being unspecific is the way to go.

But generally, the more specific, the better the movie your reader creates in their mind.

Great Writing Touches The Soul

No one ever made a decision because of a number. They need a story. — Daniel Kahneman

A cancer of actionable, soulless writing has been spreading in the digital age because anyone can now pick up a keyboard and call themselves a "writer." I'm talking about the Buzzfeed how-to articles, the articles by companies to optimize for SEO, and enough productivity and habit articles to make you question your existence.

In other words, there is a lack of great writing.

Great writing breaks you out of your normal patterning of the world and into the sublime, or hell--depends on what you're reading.

It doesn't just touch your logical, argumentative brain but your emotional one, too. It grips straight at your heartstrings and makes you want to roar with emotion.

Writing Is About Solving Problems.

If you can describe a reader's emotional problems better than they can, they will assume you have the solution. There is an entire field of writing bent on this: fiction writing.

If you can describe the world's current problems in a concise, engaging way, readers will flock to you. There is an entire field of writing devoted to this: journaling.

If you can describe the reader's life problems better then they can, they will assume you have the fix. There is an entire field of writing centered around this: copywriting.

All writing, even if it's not explicit, is about solving problems. Every. Single. One.

Each piece ties back to one of the fundamental problems of human life: survival, enjoyment of pleasures, freedom from fear, pain, and danger, sexual companionship, feeling superior, to grow and develop, to feel in control, to care and protect loved ones, and to have social approval. We have a special word for writing that doesn't tie back to one of these things.


Even super niche writing like how to create a Personal Knowledge Management System in Obsidian ties back to one of those fundamental problems. The best writers can write on a niche topic, but simultaneously solve a universal human problem, allowing it to transcend the bounds of their niche. One of my favorite examples is Sapiens by Yuval Noah Harari. His book outlines the history of humanity from homo sapiens to now, and most targets the primal human need of growth and development--you can't help but feel a sense of progress from reading that book.

So ask yourself before writing anything, what fundamental life problem(s) does this help answer?

Great Writing Is Invisible, Amazing Writing Is Glistening

If you ever think, this writing isn't very good, it's probably not very good.

Great writing is like great architecture. When architecture is great, you don't notice anything amiss with a building. Similarly, in great writing the structure disappears and you can take in the full glory of the message. The sequencing of the message just makes sense. Complicated things sound obvious through analogies, simplification, and conciseness. It seems easy to write when in fact it's really hard. But like in writing, when architecture is bad, it's terrible--the bathroom tiles are misshapen, the window is off-center--you can't help but see the flaws.

Something beautiful happens if the writing is beyond great, if it enters the realm of amazing: like amazing architecture, it glistens.

Then the architecture or writing itself becomes the art, rather then just the message. The Age Of Madness Trilogy by Joe Abercombie comes to mind. The character work is so incredible that I feel they are sitting next to me as I read. Each conversation is like poetry.

That's how you become timeless as a writer.

How Do You Grow Your Taste?

Great writing comes from great thinking which comes from a great information diet.

That's why one of the most important questions you can ask as a writer is: how can I grow my taste?

Like you grow your culinary taste through exploring and savoring new cuisines with quality unprocessed ingredients, you grow your artistic taste by creating a quality information diet. I do this in a few ways.

First, I consume only 5 mediums of information: conversation, YouTube, books, podcasts, and articles. I prioritize books, conversations, and podcasts above all else because I know these mediums prioritize timelessness and value more than short-form mediums which prioritize virality.

Second, I blend a bizarre bowl. I consume a purposefully weird mix of genres and topics. Right now, I'm reading a book on the principles of game design, a book about hypertrophy training, a book about how the languages we speak shape our cognition, and a book about the art of focus. It's the mixing of these bizzare topics that will creates novel insights and fuel my writing.

Third, I read from the inspirations of my favorite authors. If I like one author, I will likely like their inspiration. Ryan Holiday loves Seneca and Aurelius so they are crucial parts of my information diet.

Fourth, I prioritize older works over new ones. Most of society lives in a never-ending now, feeding off novel news articles and TikToks like they're heroin hits. Instead, I read older works like the Odyssey, the Bible, and The Meditations. The older a work that's still around today, the longer it will likely stick around--this is called The Lindy Effect. This is because the value they give is timeless.

Fifth and finally, I surround myself with a challenge group. A challenge group is a group of people who aren't scared of questioning you on your opinions. Many of my friends have values and political opinions different from mine, and that's exactly how I want it. It's this questioning that develops my opinions and ideas.

The Only Difference Between Short Form And Long Form Writing

Most writers shudder at the idea of writing an entire book.

It sounds like so much effort, it must take years. I'm going to let you in on a little secret: the only difference between short-form and long-form content is the amount of explanation. You can literally create a book by just combining a ton of short-form content and adding more nuance. Nuance means more:

• Reasons

• Mistakes

• Action Steps

• Personal Story Examples

• Curated Story Examples

This means you can write a book without realizing you are writing a book.

By writing many short-form pieces, getting feedback, and then combining them together after the fact, 80% of your book writing is done. This is so much more effective than writing the long-form piece from the start. You can get feedback from the beginning of the book writing process.

Gone are the days of hiking off to a cabin, smoking a cigarette, drinking some whiskey, and then coming out with your masterpiece after a year of writing only to realize, nobody cares...

You Are The Niche

Think about your favorite author; why do you read them?

It's not just because of what they write about but how and why they write about it. You might read me for my content on notetaking, learning, and gamification. But you also read me for my other interests in psychology, comedy, video games, and my bubbling, playful, energetic writing style.

Another person could write about learning, but without my voice, it wouldn't feel the same.

The topic might change, but when you read something from me you'll think, yup, there's good ol' Aidan.

What I'm trying to say is the best writers make themselves the niche.

That's why you'll be the first in line when your favorite author releases a new book. When you make yourself the niche, you diminish the competition. There is no one else who writes in your specific interests and style. You can write about anything that fascinates you, tennis, history, cooking, biology--heck write about fly fishing.

You can make anything interesting if you write with your voice.

Use Templates, But Don't Overvalue Them

If you look at the best self-help books, they almost always follow the same template:

  • Story
  • Chapters point
  • Analysis of how the story shows the chapters point
  • How you can apply it in your life

They follow this because it's a great template. It works.

But for true creativity--making something unlike anything ever before, you have to break out of the template. Templates create a box for your thinking, which helps you start but also constrains you to that box. Do you think Steve Jobs had a template for creating a personal Mac? Most people at the time thought PCs were only for no-life coders. I could never have written one of the articles I'm most proud of with a template: The Only Article On Learning Gamers Will Ever Need To Learn More In Less Time, Supercharge Memory, And Have More Fun.

It doesn't follow a guideline.

I literally dumped all of my knowledge about the connection between meta-learning, spirituality, and gamification into a page, lumped it together, and then wrote connecting prose.

Break From Your Habits And Routines

The foundation of great writing comes from experience.

You can't be a great writer if you sit at your writing desk all day (unless you're Marcel Proust, who wrote his entire 3000-page masterpiece In Search Of Lost Time, laying in his bed eating croissants, blimey). Ernest Hemingway was an ambulance driver in World War 1. Goerge Orwell lived as a tramp in London and Paris. Mark Twain was a riverboat pilot who traveled around the world.

Novel experiences are the ammunition for your writing.

Walter Patter elegantly argues for experience in one of the essays of his The Renaissance: "To burn always with this hard, gemlike flame, to maintain this ecstasy, is success in life. In a sense, it might even be said that our failure is to form habits."

We are bound by our habits. What begins as a curious inclination can soon become a prison. Our friends, family, strangers, and society at large socialize us to feel, think, and behave in certain ways. We create a mold for ourselves—particular words, turns of phrase, lines of argument, methods, genres, formats—that is hard to escape without conscious effort. Patter reminds us we have the potential to become something different, potentially greater than what we are.

My recommendation: become homeless. I'm just kidding.

Have a routine you can go back to for writing mode but every once in a while, break from it, and experience. Explore new topics. Start a new hobby. Travel to a new place. Use novel words in your writing, argue for something you don't believe, write to a different audience.

We shall always remain concealed unless we break from habit and routine and see the light.

Break The Damn Rules!!!! (Notice The Quadruple !)

Guess what, this isn't your high school English class.

You don't have to use perfect punctuation, grammar, and formality. Because, how do I say this eloquently? That's boring as shit! I have never met someone who has said, "Yes, I would like a mixture of long verbose paragraphs with vague topic sentences and perfect grammar, please."

Please, end me.

Throughout this entire article, I have had one-sentence paragraphs, sentences without an action or noun, and more. Any English teacher reading likely wants me to walk the plank. I do it because it makes the writing feel alive.

After all, aren't rules made only to be broken?

Originality Is Bullcrap.

Many non-writers have the perception that genius is a lone art.

The idea is geniuses sit in their room, tap on their desk a few times, and BOOM, an incredible idea comes out of nowhere. But in the real world, genius isn't like Ironman. Genius is a combination of lone contemplation and collaboration.

When viewed through this lens, it becomes clear originality is bullcrap.

For something to be truly original, you must have made it entirely on your own.

But that's impossible, because you are constantly getting inspired by other people and their work. What people call originality is someone claiming the main credit for a collaboration. Even Einstein admitted his theory of relativity came about from many conversations among people in Prinston.

Realizing this puts a huge weight off your chest.

Since true originality doesn't exist, you can steal like an artist. It's okay to take someone else's idea, as long as you give credit back to them and put your own spin on it. Do this enough times, and a truly new idea will come from it.

Find Your Writing Group

Realizing originality is bullcrap reveals another essential idea: great writing requires great relationships.

While writing itself is a solitary craft, the thinking that founds the writing is boosted by working with others. Benjamin Franklin founded the Junto comprised of young working men of similar social status in Philadelphia; its primary purpose was to debate questions of morals, politics, and natural philosophy, and to exchange knowledge of business affairs. Leonardo Da Vinci got his best ideas from conversing with others in the Florence coffee shops.

If you want to improve your writing, you need to find your own writing group.

Join a writing discord, take part in a live cohort course like Ship 30 For 30 or Write Of Passage, or ask one of your friends.

The Truth No Writer Wants To Admit: Your Voice Can Be Imitated

Many writers like to think their writing is completely their own, impossible to replicate.

The truth is, your voice absolutely can be imitated because there is a science to all writing. What makes up your writer's voice?:

  • Anthropological: how much you explain the why behind things
  • Actionable: how much you explain the how behind things
  • Aspirational: how inspirational your way of writing is
  • Analytical: how much you use numbers and studies in your writing
  • How long sentences or short your sentences are
  • How big or short your paragraphs are
  • Your word choice
  • Your Imagery
  • Your interests
  • Analogies you use
  • Stories you tell
  • Your humor style
  • How your writing makes people feel
  • And so on and so on

For example, my writing style is a mix of anthropological and actionable, with short and long sentences, imagery, analogies, playful bubbliness, and my interests of gamification, notetaking, learning, and more. If you know the characteristics of someone's writing, you can replicate their voice. That's why reverse engineering the best writers is one of the greatest ways to find your own voice.

It's also why making yourself the niche is so important.

Anyone can copy your voice. But they can't copy your shifting interests and the style of your writing in the context of your greater library of content.

Purposefully Practice

The secret to improving your writing and any skill is stepping out of your comfort zone.

Doing so is called purposeful practice which Ander Ericson defines in his fantastic book Peak as a specific, structured form of practice intended to improve performance.

If you don't aim for new heights in your writing consistently, you won't improve. Think of it like progressively overloading in the gym. Without slowly increasing in weight, rep, or quality of form, as you get more muscular and strong, you won't grow.

This is why I stagnated in my writing a few months ago.

I hadn't done purposeful practice inside of it for a while. I was being complacent--writing things in the same voice, with the same argumentative style and vocabulary.

Through applying the principles of purposeful practice to my writing, I'm improving once again.

Great Writing Doesn't Happen While Writing...

Great writing comes from great thinking and great thinking comes from great patience.

It's impossible to force great thinking. All you can do is create an environment that promotes it, which often means doing nothing.

Doing nothing activates your diffused mode network and leverages your most powerful writing tool: your subconscious mind.

Your subconscious mind can process way more information than your conscious mind. It's your subconscious mind responsible for those flashes of insight you get while in the shower, at the grocery store, or walking.

But your subconscious can only do its job if you're doing absolutely nothing.

No phone, no music with lyrics, no conversation. This is deeply uncomfortable. Our modern society sees productivity as output over time. In this culture, doing nothing feels like a waste of time.

In reality, it's one of the most productive things you can do.

Being A Great Writer Isn't Enough

Nowadays, you can't simply be a great writer and succeed.

You have to both know the ART of writing and the BUSINESS of writing. For two years, I ignored this advice and wrote tirelessly on my blog. Despite having decent writing, nobody was reading because I wasn't doing any form of marketing. I was like an old man on a bench with bread crumbs, but no birds. I knew the ART of writing but was ignoring the business.

Writers who succeed in the digital age know both the art and business of writing.

They understand attention is the most valuable resource and have a skill for grabbing and fostering it.

When I first started writing, I didn't pay attention to this advice, and it cost me. I wrote for a year and a half on my blog, thinking if I just wrote well enough readers would come flocking. No one did. I was like an old man on a bench with bread crumbs, but no birds.

If you want your writing seen in the digital age, you must write on a social blog and capture people's emails.

First, because social blogs have a native audience the algorithm can push your writing to. And second, because your email list is the only audience YOU ACTUALLY OWN. Your audience suffers if a social blog shuts down or adds annoying ads. But your email audience can't be touched.

I could talk for hours about The Art AND Business Of Online Writing, but instead I recommend you check out the book by the same name. It's the best book on writing in the digital age I have ever found.

Play The Infinite Game

In life, there are finite and infinite games.

Finite games are games you play to win or lose. Think a soccer match, a final to study for in school, a boss battle in a video game. Infinite games are games you play for the sake of playing in itself because they never end.

The biggest mistake you can make in your writing journey is treating it as a finite game.

When you focus too much on finite games, take shortcuts--sacrificing the learning, the soul, the joy of doing the activity for itself.

One story from my time at Cornell illuminates this terrifyingly. I was in a TA office hours for my Statistics class when a student tapped me on the shoulder and asked for help with one of the problem set questions. I helped her for 20 minutes and then turned to ask the TA another question. The student tapped me on the shoulder again. "Wait, are you not a TA?" "No," I said. Then she said something I will never forget: "Then why did you help me?"

Then why did you help me...

This is the satirical pinnacle of finite game thinking.

The good news is you can turn finite games into infinite games by simply changing your mindset. Make the intention to treat your writing as one big infinite game. One where you're never done improving, helping others, and thinking new things. Don't become one of those writers that ascribes only to trends, clickbait, and novelty. Ask yourself before writing anything:

  • Is this idea timeless?
  • Is this idea universal?
  • Is this idea interesting to me?
  • Am I the right person to write this?

Play the infinite game.

Writing Is Time Travel

The invention of writing opened the floodgates for human technological advancement.

Before writing, we had to memorize everything and pass it on orally, constraining our ability to create new knowledge. With writing you can crystalize your thinking into the outside world. This frees up your working memory to think new thoughts, compounding your knowledge over time.

In this way, writing lets you become Dr. Who, but without needing a British accent--YIPPPEEE!

You can converse with your past, present, and future selves.

There are few feelings as surreal as opening up a piece of writing your past self wrote years ago. You feel this vague sense of familiarity and companionship. You wrote these words, but simultaneously, you didn't. It was a past version of you--one with different experiences, beliefs, and environment.

Now, you can use your past selves work to fuel your current projects.

For The Love Of What Is Holy, Don't Summarize For Your Conclusion

Nothing makes a reader want to question their existence like the words "in summary."

As soon as they see these words, their boredom alarms go into overdrive. The problem with summarizing for your conclusion is it provides nothing interesting for your reader. But it does something far far worse, it disrespects them. Summarizing is like telling the reader they're too stupid to understand the piece on their own.

So what should you do instead?

Leave them on a showstopper, something which keeps them pondering for hours after they finish your article. This doesn't mean you can't summarize at all; I'm simply stating a standalone summary for a conclusion with nothing else is rubbish.

Writing Is A Conversation

When I'm writing, I like to imagine I'm sitting in an ice tub with my brother--he's not a bar kind of guy--having a conversation.

My brother is a great listener. We're also both Dutch, which means he's brutally honest. This combination means he'll listen to anything I have to say to him fully, but he won't bat an eye bashing it to the ground like he did me the first time I tried Ju Jitsu.

This makes him the perfect person to write to.

Imagining I'm writing for him also helps me write as I talk.

There's nothing as obnoxious to me as opening a piece of academic writing and getting hit with a wave of pompous over the top language in a dead robotic tone. Write like you speak, for goodness gracious. My recommendation is to imagine that you're talking to your 2-year past self or someone close to you.

Writing as you speak in the conversation has one more main benefit: it helps you fight against imposter syndrome.

Telling other people how to live their life can be hard. Who are you to say how they should live? Writing like it's a conversation helps you take the stance of the guide instead of the guru. Writer Ali Abdaal, for example, likes to write articles which start with "How I" instead of "How to."

"How I" implies he's sharing what has worked for him because it might help you, not that you have to do it.

This takes away the pressure of writing to change someone's life.

What People Call "Writing" Is Actually Many Different Things

The term "writing" encompasses ideating, researching, outlining, rough drafting, and editing.

You must understand this because many of these steps require completely different mindsets and parts of the brain. Mixing them up can be catastrophic. For example, a common mistake people make when writing is mixing rough drafting and editing.

I'll say this on it's own line because it's incredibly important: you SHOULD NOT rough draft and edit at the same time.

When you're rough drafting a piece, your goal is to get everything you can onto the page without judging. When editing, your goal is to refine and get rid of unnecessary detail. Mixing these steps enters you into what I call "snail writing." I call it snail writing because it's inevitable you'll write at a snail's pace--you're constantly questioning, deleting, moving over and over again.

It's exhausting just thinking about it.

Don't mix up the different parts of writing. The only parts that can be done together are outlining and rough drafting, and even that only applies to a shorter piece.

The Foundation Of A Great Writing Is Great Notetaking And Notemaking

Notes aren't just for remembering things in the future--that's what notetaking is for.

Notemaking, however, emphasizes active engagement with information and the connection of ideas to form novel insights. This type of note cultivation is where great writing comes from. Almost every genius in history was an avid notetaker. Leonardo Da Vinci had hundreds of notebooks filled with hundreds of thousands of words on topics like architecture, anatomy, painting, and more. Charle's Darwin had dozens of notebooks he made on his journey through the Galapagos Islands. Nikolas Luhman fueled his insane prolificity with his massive filing cabinets full of index cards he connected through a simple and elegant Zettelkasten notemaking system.

Clearly notes aren't just for remembering things, they are a tool for upgrading your thinking.

And with modern-day digital linked notetaking apps like Obsidian, our ability to notemake is more powerful than ever.

The Art Of Online Writing

Great writing has the potential to break you out of your normal framing of the world and into the sublime--or hell, depending on what you're writing.

My first experience with this was while reading Flow: The Psychology Of Optimal Experience by Mihayl Csikszentmihalyi. It clicked so many things about my childhood and experience at Cornell into place the world felt magical. Reading this article, you can cause these transformations in other people. You have a profound amount of wisdom inside of you.

If you don't write it down, it will be lost to the ages.

After spending 1000+ hours in the Personal Knowledge Management community, I have found it's surprisingly simple as well (but by no means easy). All you need is a notetaking app, a system for collecting, connecting, and creating out of information you consume, and follow three rules: create short notes, connect your notes, nurture your notes.

If you want to learn more, you should check out my Obsidian Beginner Resource List.

Save yourself countless hours of time and energy looking for the best Obsidian learning resources. It includes all of the resources I wish I had on Obsidian 3 years ago, including the best creators to follow, links to immerse yourself in the community, and my most popular curated content on Obsidian.